Key West Rentals
From $225 per night (USD)HomeAway
Luxurious monthly rental in mid-town
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
28 Day minimum Rental: Tucked away behind a contemporary privacy fence and an attractive cobblestoned driveway is this h ...
From $225 per night (USD)HomeAway
From $329 per night (USD)VRBO
Secret Villa II @ Old Town: with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa II - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own pri ...
From $329 per night (USD)VRBO
From $1000 per night (USD)HomeAway
Private Home with Sun-filled Pool-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Backyard pool offers lots of sunshine. This home sits in Key Lime Grove Subdivision which I was born and raised in. It ...
From $1000 per night (USD)HomeAway
From $225 per night (USD)VRBO
Sunrise Suite 203-Fun and Relaxation of Resort Living,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suite 203 vacation rental in Key West is a quiet alternative to the bustling noise of downtown Key West. Locate ...
From $225 per night (USD)VRBO
From $140 per night (USD)HomeAway
~ COPA CABANA ~ Cute Conch Home w/ Pvt Pool In "Old Town." Live Like A Local!
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
About THE PROPERTY: Open the door to Key West’s past when you arrive at Copa Cabana, a quaint, 1923 “shotgun” house th ...
From $140 per night (USD)HomeAway
From $200 per night (USD)VRBO
Ann Street Cottage: A bright and airy home near Duval Street
- Bedrooms:
- 2.5
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom c ...
From $200 per night (USD)VRBO
From $1000 per night (USD)HomeAway
Luxury rental with heated private pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This is a Beautiful tropical oasis with a heated private pool. You will have two beach cruisers to use during your stay ...
From $1000 per night (USD)HomeAway
From $215 per night (USD)VRBO
Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our Key West Condo, the Key West Cabana. This spacious well appointed 2 bedroom, 2 full bath condo that’s ri ...
From $215 per night (USD)VRBO
From $325 per night (USD)HomeAway
Downtown Cottage just off famous Duval Street-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stay in the Conch Republic Consul General's Cottage. Historic Carriage House is located a few blocks from famous Duval S ...
From $325 per night (USD)HomeAway
From $329 per night (USD)VRBO
"Casa Catalina" Private Home In Old Town- Pool- Steps From Duval Street-Updat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Classic Conch house with all of the historic feel and all of the modern conveniences. Larger than most cigar maker’s co ...
From $329 per night (USD)VRBO
From $484 per night (USD)HomeAway
Key West Dreamin' ~ Private Pool Near Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities ...
From $484 per night (USD)HomeAway
From $140 per night (USD)VRBO
~ LOLA'S PLACE ~ Stunning Home w/Pool, parking in the <3 of Key West. Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About THE PROPERTY: Lola's Place features everything you might want or need for your monthly vacation in Key West, sta ...
From $140 per night (USD)VRBO
From $578 per night (USD)HomeAway
~ Chick-A-Pea Cottage ~ Breathtaking Home w/ Pool & Parking, 1 Block to Duval
- Bedrooms:
- 3.5
- Bathrooms:
- 4
- Sleeps:
- 8
About THE PROPERTY: Chick-A-Pea is a traditional Key West cottage that has undergone a complete renovation. The charm ...
From $578 per night (USD)HomeAway
From $214 per night (USD)VRBO
Elizabeth Retreat: A three bedroom historic home in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just ...
From $214 per night (USD)VRBO
From $275 per night (USD)HomeAway
Positively Poolside - 2 Bedroom 2 1/2 Bath Townhome in Key West Golf Club
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
This fantastic 2 bedroom 2 1/2 bath townhome is in a gated community nestled among the fairways and greens of the covete ...
From $275 per night (USD)HomeAway
From $85 per night (USD)VRBO
Key Lime Pie Suite at Top Of Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart ...
From $85 per night (USD)VRBO
From $325 per night (USD)HomeAway
Island Hideway Minutes From Higgs Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Higgs Beach Hideaway offers all the amenities for a long term stay in Key West. This tropical home features 3 bedrooms w ...
From $325 per night (USD)HomeAway
From $957 per night (USD)VRBO
~ MAISONS de LUXE ~ 2 Stunning Homes w/ Private Pool ON DUVAL. Dogs OK!
- Bedrooms:
- 7.5
- Bathrooms:
- 6
- Sleeps:
- 12
About THE PROPERTY and BED CONFIGURATIONS: GRAND MAISON (the Main House) is located in the Gallery District right on Du ...
From $957 per night (USD)VRBO
From $450 per night (USD)HomeAway
Three bedroom, two bath with private pool 2 blocks from Duval street
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This historic Conch House has been completely redesigned and custom crafted by 2 architects as their home away from home ...
From $450 per night (USD)HomeAway
From $425 per night (USD)VRBO
Villa Paradiso: A unique mid-town paradise
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This mid-town Key West home is recently refreshed with light colors and beautiful British Colonial furnishings. It featu ...
From $425 per night (USD)VRBO
From $265 per night (USD)HomeAway
Bonaire Suite- A beautiful Island Retreat- Shared Pool- Gated compound
- Bedrooms:
- 2.5
- Bathrooms:
- 1
- Sleeps:
- 6
Bonaire Suite is bi-level suite with 2 queen beds upstairs separated by a privacy curtain and a queen sofa bed in the li ...
From $265 per night (USD)HomeAway
From $275 per night (USD)VRBO
OCEANFRONT ECSTASY - KW Beach Club #304
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy endless views just feet away from the tranquil waters of the Atlantic Ocean. “Beach Club #304” is a serene waterfr ...
From $275 per night (USD)VRBO
From $186 per night (USD)HomeAway
Beachfront, Deluxe 3 BR oceanfront condo, great rates
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Oceanfront at Smathers Beach in Beautiful Key West, Florida. Why pay for a hotel, when you can enjoy your own private oa ...
From $186 per night (USD)HomeAway
From $579 per night (USD)VRBO
Key West Wabi Sabi ~ Authentic Key West Cottage
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island livi ...
From $579 per night (USD)VRBO
From $315 per night (USD)HomeAway
Island Dream House one block from the Historic Seaport
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This charming historic Conch cottage is located on a quaint lane between Eaton and Caroline Streets one block from the h ...
From $315 per night (USD)HomeAway
From $1389 per night (USD)VRBO
4Br/4.5Ba Historic Home With Pool In Old Town
- Bedrooms:
- 5.5
- Bathrooms:
- 3
- Sleeps:
- 10
This historic seasonal rental with its cypress siding was built circa 1886. Your hosts, who have spent a considerable pa ...
From $1389 per night (USD)VRBO
From $240 per night (USD)HomeAway
DUVAL BREEZE Great Location, Walk Everywhere, Overlooks Duval, Rooftop Pool!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and g ...
From $240 per night (USD)HomeAway
From $400 per night (USD)VRBO
Top Of Duval - Your Own Private 6 Bedroom Hotel
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart ...
From $400 per night (USD)VRBO
From $75 per night (USD)HomeAway
All inclusive sailing charter .70 foot catamaran
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
A large sailboat capable of all types of entertainment. Large bedrooms and the largest bathrooms I have seen on this siz ...
From $75 per night (USD)HomeAway
From $148 per night (USD)VRBO
~ CASABLANCA ~ Fabulous Cottage w/ HEATED Pool, Parking & Tons of Sun!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
About THE PROPERTY: Casablanca is the perfect Key West vacation rental for those seeking a good time, but who would li ...
From $148 per night (USD)VRBO
From $110 per night (USD)HomeAway
Turn lemons into lemonade Jan. Feb. & March. Prices lowest ever!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
STERILIZED WITH 4 QUAD CLEANING SYSTEM ...
From $110 per night (USD)HomeAway
From $50 per night (USD)VRBO
Condo 2 br, Ocean view from Balcony, Pets Welcome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This condo is privately owned and managed. No condo fees. Condo's features one and two bedrooms, with a king bed in the ...
From $50 per night (USD)VRBO
From $250 per night (USD)HomeAway
Ole Olivia! 4 bedroom- MONTHLY RENTAL ONLY- Open for Feb and March 2019
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
You will be delighted with this wonderful home with recent renovations, perfectly placed pool, and plenty of outdoor liv ...
From $250 per night (USD)HomeAway
From $150 per night (USD)VRBO
South Street Cottage: Bright & sunny in the Casa Marina district
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
28 DAY MINIMUM RENTAL A bright and sunny pool home situated on a quiet street in the Casa Marina district of Key West. ...
From $150 per night (USD)VRBO
From $649 per night (USD)HomeAway
Key West Golf Club - Completely Renovated - Tree House Too.
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
You may rely on the accuracy of the calendar that appears on VRBO. Please note we are flexible with dates. It is not re ...
From $649 per night (USD)HomeAway
From $260 per night (USD)VRBO
~TROPICAL DREAM~ World Class Luxury Home w/Pool, Roma Spa & Parking. Dogs OK!
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
About THE PROPERTY: We guarantee that Tropical Dream will fulfill even the highest expectations. Amazing LUXURY Vacati ...
From $260 per night (USD)VRBO
From $1000 per night (USD)HomeAway
Stone Throw Famous Duval Street Location-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
House is located just steps from famous Dvual Street. Duval Street stretches from the Atlantic Ocean to the Gulf of Mexi ...
From $1000 per night (USD)HomeAway
From $356 per night (USD)VRBO
~POTTER'S COTTAGE~ Historic Home w/ Private Heated Pool In Prime Location!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About THE PROPERTY: Experience hotel-like 5-star luxury but with the exclusive privacy of this adorable Key West home. ...
From $356 per night (USD)VRBO
From $940 per night (USD)HomeAway
~ VILLA JOSINE ~ Luxurious "Old Town" Home w/ 18'Heated Pool & Parking!
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 8
About THE PROPERTY: Villa Josine is an amazingly beautiful home located in one of the most sought after locations in ...
From $940 per night (USD)HomeAway
From $371 per night (USD)VRBO
Hyatt Beach House- 2 Bedroom Located On The Gulf With Private White Sand Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This villa is for seven night rentals with check-in and check-out on Fridays, Saturdays and Sundays ONLY! Great destin ...
From $371 per night (USD)VRBO
From $217 per night (USD)HomeAway
~ SEAS THE DAY ~ Cute Condo w/ Pool & Private Parking! Walk to Ft Zach Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
About THE PROPERTY: Historic Key West Vacation Rentals invites you to enjoy this vacation rental aptly named "Seas the ...
From $217 per night (USD)HomeAway
From $329 per night (USD)VRBO
Secret Villa I @ Old Town with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa I - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own priv ...
From $329 per night (USD)VRBO
From $100 per night (USD)HomeAway
Lennon's Lodge-2 BR Luxury Cottage w/Private 6 person Spa, 2 Heated Pools!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Part of 4 exclusive units at Abbey Road in a private, gated compound just off Duval Street The original Cuban tile has ...
From $100 per night (USD)HomeAway
From $126 per night (USD)VRBO
Ocean views and beach breezes at La Brisa's #303 West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
28 DAY MINIMUM RENTAL Let "the breeze" of La Brisa cool you as you relax on your balcony overlooking a natural water sa ...
From $126 per night (USD)VRBO
From $130 per night (USD)HomeAway
Namaste 'the spirit within me salutes the spirit within you'
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom B ...
From $130 per night (USD)HomeAway
From $349 per night (USD)VRBO
Charming Key West Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
True Key West flavor! 1 Bedroom 1 Bathroom apartment newly remodeled and updated Conch House located on White St.with h ...
From $349 per night (USD)VRBO
From $250 per night (USD)HomeAway
Bottom's Up Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Perfection in the Meadows awaits you in a pristine Florida Bungalow. This two bedroom, two bathroom home offers all the ...
From $250 per night (USD)HomeAway
From $85 per night (USD)VRBO
Mile Zero Suite at Top Of Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart ...
From $85 per night (USD)VRBO
From $59 per night (USD)HomeAway
Dec 19- 26 2020 Only - Oceanfront Key West Condo - Quiet and away from crowds
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our unit at Coconut Beach Resort Note: This is available for the dates Saturday 12/19/20 to Saturday 12/26/ ...
From $59 per night (USD)HomeAway
From $240 per night (USD)VRBO
~STEAMPLANT 207~ Luxury 3-Story Condo w/ Pvt Rooftop Pool & Amazing Views!
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
THE PROPERTY: Steamplant 207! Two Level, 5 Star Luxury Residence Breathtaking panoramic views of Key West. * Private Ro ...
From $240 per night (USD)VRBO
From $200 per night (USD)HomeAway
One bedroom, two bath, sleeps 2 - Monthly Rental- AVAILABLE FOR JANUARY
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
This cozy and comfortable home will transition you from the hustle and bustle of your everyday life to the relaxing hist ...
From $200 per night (USD)HomeAway
From $450 per night (USD)VRBO
The Caroline House Estate
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $450 per night (USD)VRBO
From $485 per night (USD)HomeAway
~ SOUTHARD COMFORT ~ Historic Home w/ Heated Pool, Parking & Quiet Location!
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
About THE PROPERTY: “Southard Comfort” is true Island living in Historic "Old Town" Key West. Nancy & Carl welcome yo ...
From $485 per night (USD)HomeAway
From $350 per night (USD)VRBO
Duval Square Courtyard Condo is just steps from the action
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
In the heart of Old Town, convenient to everything, this condo is set above a brick and tree lined courtyard that includ ...
From $350 per night (USD)VRBO
From $275 per night (USD)HomeAway
Beach Club #103 - Unique oceanfront living with breathtaking views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $275 per night (USD)HomeAway
From $414 per night (USD)VRBO
Key West Oasis, Seperate Cottage, Very Private Pool & Back Yard
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $414 per night (USD)VRBO
From $178 per night (USD)HomeAway
Key West home w/shared pool and just steps from historic Old Town
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
Bright Key West Beauty Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $178 per night (USD)HomeAway
From $315 per night (USD)VRBO
~FAIR WINDS @ THE FOUNDRY~ Updated Townhome w/ Pool, Close To Ft Zach Beach!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
About THE PROPERTY: Fair Winds at the Foundry is a gorgeous coastal 3 story, 2 bedroom, 2.5 bath immaculate light and ...
From $315 per night (USD)VRBO
From $150 per night (USD)HomeAway
Majestic Escape near Duval! Pool, wifi, renovated 2/2 1/2, private courtyard.
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
You will love our newly renovated 2 bed/ 2 1/2 bath private townhome in a secure community. Perfect location. This prope ...
From $150 per night (USD)HomeAway
From $55 per night (USD)VRBO
ShangriLa Suite / Queen Studio / Sleeps 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $55 per night (USD)VRBO
From $150 per night (USD)HomeAway
Luxurious Key West Pool Home block from Duval & completely remodeled in 2017!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Old Town refuge barely a block from world famous Duval Street with glimpse of Key West Light House! Located in the Histo ...
From $150 per night (USD)HomeAway
From $450 per night (USD)VRBO
Conch Republlic Cottage - Nightly Group Rental Unit - Sleeps up to 10 off Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
This nightly group rental consists of 3 separate units, Porchside Paradise, Orange Blossom Suite and Deckside Suite. Co ...
From $450 per night (USD)VRBO
From $260 per night (USD)HomeAway
La Casa del Luces- Steps from the Beach and Duval - Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
La Casa de Luces - Come to relax or to play while enjoying the spectacular sunsets and the blue waters of Key West! This ...
From $260 per night (USD)HomeAway
From $322 per night (USD)VRBO
~ POINCIANA PARADISE ~ Historic Home w/ Hot Tub & Parking for 2 Near Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
About THE PROPERTY: The Poinciana Paradise vacation rentals are located on a tiny lane in 'Old Town' Key West. This ...
From $322 per night (USD)VRBO
From $150 per night (USD)HomeAway
KEY WEST CHARMING Lounge on the Patio or Shared Pool, Walk to Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Recently painted, upgraded with new floors and updated kitchen Key West Charming is just the perfect home away from home ...
From $150 per night (USD)HomeAway
From $180 per night (USD)VRBO
BRISA DEL MAR Atlantic Ocean Condo, Next to Beach, Kayaks + Paddleboard Fun!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy spectacular ocean views from this lovely rental! This two bedroom, two bath condominium is located oceanfront in ...
From $180 per night (USD)VRBO
From $742 per night (USD)HomeAway
~ GRAND MAISON ~ Amazing Home On Duval w/ Heated Pool & Off Street Parking
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Grand Maison on Duval is located in the Gallery District right on Duval Street near the Southernmost Point ...
From $742 per night (USD)HomeAway
From $425 per night (USD)VRBO
Pete's Cottages: Twin Cypress cottages steps from Duval
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypre ...
From $425 per night (USD)VRBO
From $182 per night (USD)HomeAway
THOMPSON'S COURT - Mid Town Getaway with pool & jacuzzi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL Thompson's Court is the quintessential south Florida home: a sprawling, peach-colored, ranch-styl ...
From $182 per night (USD)HomeAway
From $125 per night (USD)VRBO
Key West Coop - our tropical oasis in the Historic District close to everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully remodeled Cottage in the Historic District of Key West. Walk or ride your bike to anywhere on the island. ...
From $125 per night (USD)VRBO
From $75 per night (USD)HomeAway
Harbour Place 115 in Truman Annex Key West
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Harbor Place is one of the most prestigious properties in Key West! This unit offers breath taking water views overlook ...
From $75 per night (USD)HomeAway
From $230 per night (USD)VRBO
Pete's West Cottage steps from Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypre ...
From $230 per night (USD)VRBO
From $365 per night (USD)HomeAway
Downtown Location in Historic District-No Contact Check-In
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in the Conch Republic Consul General's Cottage. This one bedroom cottage is located in the historic district and o ...
From $365 per night (USD)HomeAway
From $179 per night (USD)VRBO
Rent a Piece of Paradise, Best Location on the Island!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $179 per night (USD)VRBO
From $170 per night (USD)HomeAway
~ SEA VISTA ~ On the Gulf w/private DOCK, Pet Friendly, Pvt Pool & Parking
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 7
About THE PROPERTY: Just steps away from putting your toes in the ocean... Ever dream of waking up, walking out your ...
From $170 per night (USD)HomeAway
From $180 per night (USD)VRBO
LINGER LONGER Private Home, Steps to Pool, Family Friendly, Walk to Duval!
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
Just imagine stepping out of the rental and stepping right into the pool! Enjoy a carefree vacation in this beautifully ...
From $180 per night (USD)VRBO
From $185 per night (USD)HomeAway
Tom's Chicken Coop: Nice Ocean View, Pool, Renovated, Close to Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located only two miles from Duval 1800 Atlantic Blvd offers the best of both worlds; close to downtown without most of t ...
From $185 per night (USD)HomeAway
From $450 per night (USD)VRBO
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $450 per night (USD)VRBO
From $159 per night (USD)HomeAway
~ MY HAPPY PLACE ~ Tropical Home w/ Private Pool In Heart of 'Old Town' KW
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About THE PROPERTY: My Happy Place is an exemplary renovation of an historic, Key West house. It retains its original ...
From $159 per night (USD)HomeAway
From $380 per night (USD)VRBO
Havana Lane: An updated classic conch cottage with still a rustic edge!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming conch cottage has gone through some wonderful changes in 2019! Enter the private courtyard of the home, t ...
From $380 per night (USD)VRBO
From $240 per night (USD)HomeAway
Cuban Club Suites - 2 Bed/2 Bath - Shared Pool - Sleeps up to 8- Summer Rates
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Built in 1917 as a 'club' for Cuban cigar makers and their families as their 'home away from home', it soon became the c ...
From $240 per night (USD)HomeAway
From $520 per night (USD)VRBO
Pavilion Villa ~ A Private Paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a ha ...
From $520 per night (USD)VRBO
From $150 per night (USD)HomeAway
Albury Bungalow: A quiet retreat in the Meadows
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
28 DAY MINIMUM RENTAL A perfect spot for two couples, two singles or others wanting privacy as well as togetherness. Th ...
From $150 per night (USD)HomeAway
From $59 per night (USD)VRBO
Beautiful views and ready access to Duval Street festivities and boat docks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two bedroom condo units in the premier Galleon Resort with unique access to dockage and rental boats. The units include ...
From $59 per night (USD)VRBO
From $85 per night (USD)HomeAway
Paradise Penthouse Suite at Top of Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart ...
From $85 per night (USD)HomeAway
From $150 per night (USD)VRBO
Blue Coral: A Private Oasis In The Heart Of Old Town Key West
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 6
This house was renovated / rebuilt in 2014. I rent SAT to SAT. I can do 5 to 6 nights in that time frame. I DON"T RENT ...
From $150 per night (USD)VRBO
From $229 per night (USD)HomeAway
Cozy Condo in the Truman Annex - Fully Updated 2BR/1BA - Footsteps from pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Conch Life Condo is a cozy 2 bedroom / 1 bathroom condo in the Truman Annex to fully experience the conch life. Full ...
From $229 per night (USD)HomeAway
From $275 per night (USD)VRBO
Beach Club #204 - Unique Oceanfront living
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $275 per night (USD)VRBO
From $260 per night (USD)HomeAway
ARTIST'S HOUSE @ Duval Square by Rent Key West Vacations - Located on Duval
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom, 2.5 bath rooftop town home is located within the quaint community of Duval Square. Beautifully decorated ...
From $260 per night (USD)HomeAway
From $225 per night (USD)VRBO
TRUMAN'S HIDEAWAY Huge Patio, Grill, Shared Pool, Family Fun + Sunset View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
It’s hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's ...
From $225 per night (USD)VRBO
From $203 per night (USD)HomeAway
Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes th ...
From $203 per night (USD)HomeAway
From $200 per night (USD)VRBO
Shipyard Palms: A first floor condo in the Shipyard of Truman Annex
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of Old Town, with the beautiful community of private homes and condominium of Truman Annex, this Shipyard C ...
From $200 per night (USD)VRBO
From $150 per night (USD)HomeAway
Truman Annex Unit 177
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Hemingway's Cottage is the first floor of a two story town home in the award winning private gated community Truman Anne ...
From $150 per night (USD)HomeAway
From $500 per night (USD)VRBO
Flower Power House ~ Boho Beautiful
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 15
Boho beautiful, the free-spirited presence of the Key West Flower Power House vacation rental, has much more in common w ...
From $500 per night (USD)VRBO
From $130 per night (USD)HomeAway
Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
We want to let you know that your safety and comfort is our priority. Past reviews have always praised how clean our con ...
From $130 per night (USD)HomeAway
From $425 per night (USD)VRBO
Craig & Cindy's Key West Truman Annex Porter House (4 bedroom with private pool)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The two story Truman Annex Porter House is the largest of our Key West properties and features 4 bedrooms and a private ...
From $425 per night (USD)VRBO
From $350 per night (USD)HomeAway
TROPICAL DREAMING Private Home with Private Pool, Patio + BBQ, Pet Friendly!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Do not look any further! Your perfect vacation home rental is right here! Offering a private pool with lounge chairs and ...
From $350 per night (USD)HomeAway
From $70 per night (USD)VRBO
Heart of Old Town, Truman Annex Beautiful Large 1st Flr, 2BR KING/twins, Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! Large front yard and porch to watch Key ...
From $70 per night (USD)VRBO
From $100 per night (USD)HomeAway
Peaceful One Bedroom Retreat Located Blocks From Duval Street And The Harbor.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This one bedroom loft apartment with full kitchen and laundry has everything you need for an extended stay! Located on o ...
From $100 per night (USD)HomeAway
From $200 per night (USD)VRBO
Spectacuar views of Smather's Beach and the Atlantic Ocean
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Our Home Away from home. Our condo is located in the LaBrisa complex which is a gated community across from ...
From $200 per night (USD)VRBO
From $751 per night (USD)HomeAway
~THE TRUMAN SUITES ~ 5 Separate Luxury Suites w/ Heated Pool! Great Location!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 18
About THE PROPERTY: Just steps from everything Key West, The Truman Suites consists of 5 separate fully equipped suites ...
From $751 per night (USD)HomeAway
From $70 per night (USD)VRBO
The Galleria Unit #14 ~ A Stones throw from Duval St! Bikes Included!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This quaint, cute and cozy Studio unit is on a second floor is nothing fancy and only 3 blocks from the action on Duval ...
From $70 per night (USD)VRBO
From $180 per night (USD)HomeAway
~LEMONADE MERMAID~ Dog-Friendly, Heated POOL, Fenced Yard. Off street parking
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
About THE PROPERTY: You’re going to delight being in Lemonade Mermaid! This adorable gingerbread cottage with amazing ...
From $180 per night (USD)HomeAway
From $125 per night (USD)VRBO
Historic District-Pool View-Beach Nearby-No Contact Check-In
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom, fully furnished condominium is located in the Truman Annex, a gated community of private homes and condo ...
From $125 per night (USD)VRBO
From $400 per night (USD)HomeAway
4 bd w/loft Condo w/ boat slip Pelican Landing St John
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $400 per night (USD)HomeAway
From $300 per night (USD)VRBO
Aah Paradise @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
AAH PARADISE This Foundry townhouse is a Bostonian style 3 level home located in Old Town Key West. This home has been r ...
From $300 per night (USD)VRBO
From $571 per night (USD)HomeAway
Special Rates For Both Weekly And Monthly!
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful vacation home in Key West in the award-winning Truman Annex, this 3 story, 4 bedroom 3.5 bath townhome sits on ...
From $571 per night (USD)HomeAway
From $207 per night (USD)VRBO
Island Breezes @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This charming second floor condominium features two bedrooms, and one full bath with views of the Truman Waterfront Park ...
From $207 per night (USD)VRBO
From $209 per night (USD)HomeAway
Flip Flop Retreat Townhome in Quiet Convenient Location
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 5
Two bedroom, 2.5 bath townhome in Truman Annex two blocks to Duval Street. Quiet, clean, comfortable oasis in perfect l ...
From $209 per night (USD)HomeAway
From $59 per night (USD)VRBO
Lock-Out Unit at the Galleon Resort - Best Resort Location In KW
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio(lock-out) for rent 5th floor. The Galleon Resort has its own marina, fishing charters on-site, tiki bar that serv ...
From $59 per night (USD)VRBO
From $349 per night (USD)HomeAway
SPECIAL PRICING May 2021 !" -OCEAN FRONT! 90 FT BALCONY Spectacular Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Notice: Due to Corona Virus We suggest you purchase "Cancel For Any Reason Insurance". VRBO offers insurance at time of ...
From $349 per night (USD)HomeAway
From $257 per night (USD)VRBO
High Tide @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
If you have high expectations you are going to enjoy staying at High Tide. You are within walking distance to restaurant ...
From $257 per night (USD)VRBO
From $136 per night (USD)HomeAway
**SUNDRENCHED REFLECTIONS @ SUNSET MARINA** Bayfront Condo + LAST KEY SERVICES..
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $136 per night (USD)HomeAway
From $300 per night (USD)VRBO
License to Chill in the Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
This unit has been remodeled with a complete new kitchen. The Master bedroom has a King bed, while the guest bedroom has ...
From $300 per night (USD)VRBO
From $2507 per night (USD)HomeAway
**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
- Bedrooms:
- 16
- Bathrooms:
- 13
- Sleeps:
- 32
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $2507 per night (USD)HomeAway
From $288 per night (USD)VRBO
Latitude Penthouse Key West B417: 2 BR, 2 BA Condominium in Key West, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Top floor penthouse ocean-view condominium at 1800 Atlantic in the highly desirable B building. This unit has recently b ...
From $288 per night (USD)VRBO
From $872 per night (USD)HomeAway
**THE LIME & THE COCONUT @ OLD TOWN** 6BR/6BA Compound + LAST KEY SERVICES..
- Bedrooms:
- 9
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $872 per night (USD)HomeAway
From $142 per night (USD)VRBO
** PERFECT HARMONY @ CASA EAST** Home + Pool / Near Beach + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $142 per night (USD)VRBO
From $763 per night (USD)HomeAway
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 9
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $763 per night (USD)HomeAway
From $240 per night (USD)VRBO
Botanical Island Delight C120: 2 BR, 2 BA Condominium in Key West, Sleeps 4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This unit has a king in both bedrooms. 1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smather ...
From $240 per night (USD)VRBO
From $161 per night (USD)HomeAway
@ Winter in Paradise Available Jan 1st - April 1st 2021 - Discounts @
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Lovely 2nd floor unit. Beautifully renovated, This unit has luxurious finishes. Both bedrooms and the living room open o ...
From $161 per night (USD)HomeAway
From $111 per night (USD)VRBO
**DRIFTWOOD DREAMS @ 1800 ATLANTIC** Beachside Condo & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $111 per night (USD)VRBO
From $136 per night (USD)HomeAway
**A TOAST TO SUNSET @ SUNSET MARINA** Bayfront Condo & Pool + LAST KEY SERVICES.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $136 per night (USD)HomeAway
From $274 per night (USD)VRBO
Penthouse Level Ocean Views- CHECK FOR LAST MINUTE SPECIALS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PROFESSIONAL CLEANING PER CDC GUIDELINES BEFORE & AFTER EACH STAY You feel the excitement the moment you arrive. The war ...
From $274 per night (USD)VRBO
From $300 per night (USD)HomeAway
2 bdrm Condo w/ boat slip Pelican Landing Harbor Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...
From $300 per night (USD)HomeAway
From $273 per night (USD)VRBO
**LA PETITE PENTHOUSE @ THE ANNEX** Elegant Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $273 per night (USD)VRBO
From $414 per night (USD)HomeAway
Saltwater Angler @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Large corner unit with three balconies and waterfront sunset view. Oversized living room with plenty of seating includin ...
From $414 per night (USD)HomeAway
From $343 per night (USD)VRBO
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $343 per night (USD)VRBO
From $125 per night (USD)HomeAway
"TORTOISE SHELL II" ~ Comfortable, Modern Condo Two Blocks from Duval!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CLASSIC KEY Tortoise Shell II is an elegant two bedroom, 2 bath condominium one block off of famous Duval Street. Secon ...
From $125 per night (USD)HomeAway
From $80 per night (USD)VRBO
Paradise Palm at the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Paradise Palm***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***This is a beautiful, private two-story open plan townhome ba ...
From $80 per night (USD)VRBO
From $207 per night (USD)HomeAway
Angler's Retreat @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A stay in Anglers Retreat is more then just a rental, but will be part of your Key West vacation experience. In addition ...
From $207 per night (USD)HomeAway
From $181 per night (USD)VRBO
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home + Pool + LAST KEY SERVICES.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $181 per night (USD)VRBO
From $171 per night (USD)HomeAway
Hemingway's Hammock @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $171 per night (USD)HomeAway
From $382 per night (USD)VRBO
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $382 per night (USD)VRBO
From $452 per night (USD)HomeAway
**BAHAMIAN BAMBOO @ THE ANNEX** Chic Home By Duval & Beach + LAST KEY SERVICES.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $452 per night (USD)HomeAway
From $214 per night (USD)VRBO
Eaton Manor - 2 Bedroom Condo with a Shared Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...
From $214 per night (USD)VRBO
From $414 per night (USD)HomeAway
Paradise on the Ocean @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This two bedroom condo is located in the Truman Annex, Key West's premier residential community in Harbour Place on the ...
From $414 per night (USD)HomeAway
From $584 per night (USD)VRBO
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $584 per night (USD)VRBO
From $900 per night (USD)HomeAway
!!SPECIAL SEPTEMBER WEEKLY OR MONTHLY RATES!!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
When you are seeking one of the best large home accommodations, look no have found Admirals Treasure, a fabulous 4 bedr ...
From $900 per night (USD)HomeAway
From $329 per night (USD)VRBO
Special Rates For Both Weekly And Monthly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This Private home is located in the historic Truman Annex of old town Key West, where you can get away from it all while ...
From $329 per night (USD)VRBO
From $207 per night (USD)HomeAway
Southard Comfort in the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
LOCATION, LOCATION, LOCATION and under new ownership. Southard Comfort is on Southard Street in the TRUMAN ANNEX, which ...
From $207 per night (USD)HomeAway
From $165 per night (USD)VRBO
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
We understand that these are unprecedented times and no one knows what tomorrow will bring. On July 13, 2020 the City of ...
From $165 per night (USD)VRBO
From $207 per night (USD)HomeAway
Dolphin Delight @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $207 per night (USD)HomeAway
From $288 per night (USD)VRBO
Somewhere on the beach: 2 BR, 2 BA Condominium in Key West, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Somewhere on the Beach has Amazing sweeping views of the Atlantic. April - July 14th 2021 this unit will be undergoing a ...
From $288 per night (USD)VRBO
From $120 per night (USD)HomeAway
Enjoy More Privacy in a Truman Annex End Unit Townhome
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
Contact us about special Summer Rates! Absolute Best Location! Our Townhome is set in the tranquil verdant gardens of ...
From $120 per night (USD)HomeAway
From $134 per night (USD)VRBO
@@ Boat House Harbor May 2021 available @@
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This property has been totally renovated and features a fantastic roll in custom shower which is fully wheelchair access ...
From $134 per night (USD)VRBO
From $171 per night (USD)HomeAway
Alhambra @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $171 per night (USD)HomeAway
From $171 per night (USD)VRBO
SPECTACULAR PRICE!!! Island Spa @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This Shipyard unit has a Queen bed, one bathroom, very sunny, bright condo.It has a very nice large deck balcony facing ...
From $171 per night (USD)VRBO
From $353 per night (USD)HomeAway
**SUNSET DREAMS @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $353 per night (USD)HomeAway
From $218 per night (USD)VRBO
**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $218 per night (USD)VRBO
From $288 per night (USD)HomeAway
Key West On My Mind: 2 BR, 2 BA Condominium in Key West, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stunning 2 bedroom ocean-view oasis vacation rental at the fabulous 1800 Atlantic in Key West. Our family owned unit has ...
From $288 per night (USD)HomeAway
From $382 per night (USD)VRBO
**BANANA BLOSSOMS @ THE ANNEX** Lush Villa by Beach + Pool + LAST KEY SERVICES
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $382 per night (USD)VRBO
From $200 per night (USD)HomeAway
Tropical Old Town Bungalow** Private hot tub** Shared pool** Great Location**
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Great Location*Private Hot Tub*Close to Duval Welcome to paradise! This Tropical Old Town Bungalow is located perfectly ...
From $200 per night (USD)HomeAway
From $179 per night (USD)VRBO
"CARIBBEAN SOUL" ~ 3 Bedroom, 3.5 Bath , Sleeps 6, Private Pool & Parking!
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 6
QUINTESSENTIAL KEY WEST HOME LEAVING NOTHING MORE TO BE DESIRED... Framed by a white picket fence you will be welcomed t ...
From $179 per night (USD)VRBO
From $50 per night (USD)HomeAway
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $50 per night (USD)HomeAway
From $75 per night (USD)VRBO
Boli Townhouse - Luxury Rental in gated Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We want you to know that your safety and comfort while in Key West is our utmost priority. We have upgraded our meticulo ...
From $75 per night (USD)VRBO
From $414 per night (USD)HomeAway
Tropical Executive @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $414 per night (USD)HomeAway
From $350 per night (USD)VRBO
Galleon Resort Waterfront Luxury in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...
From $350 per night (USD)VRBO
From $185 per night (USD)HomeAway
**KEYS KOKOMO @ BEACHSIDE** Home / Pool Near Beach + LAST KEY SERVICE...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $185 per night (USD)HomeAway
From $205 per night (USD)VRBO
Tom's 2000sf Direct Oceanfront Penthouse. Renovated, Heated Pool, Close To Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Covid Cancellation Policy: Until there is a Corona vaccine a 100% refund will be given up until the day of arrival. No ...
From $205 per night (USD)VRBO
From $236 per night (USD)HomeAway
Happy Hour Haven @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
It is always "Happy Hour" in this lovely second floor condo. Coffee in the morning, cocktails anytime, or just relax wi ...
From $236 per night (USD)HomeAway
From $156 per night (USD)VRBO
**KEY WEST STATE OF MIND @ THE GOLF CLUB** Serene Home + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...
From $156 per night (USD)VRBO
From $117 per night (USD)HomeAway
30 night minimum stay requirement. Boater's Dream 2 Bedroom 2 Bathroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
30- Night minimum stay: Private and quiet, this luxurious unit is an ideal place for relaxing and you are only minutes a ...
From $117 per night (USD)HomeAway
From $599 per night (USD)VRBO
Extra large Conch style home in Oldtown with privavte pool AND dock!
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 10
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...
From $599 per night (USD)VRBO
From $207 per night (USD)HomeAway
Southernmost Sanctuary @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Southernmost Sanctuary is a beautiful two bedroom, one bath condominium has recently been updated located in the Shipyar ...
From $207 per night (USD)HomeAway
From $300 per night (USD)VRBO
Special Rates For Both Weekly And Monthly!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This whimsical unit has a whimsy nautical feel on the first two levels with the blue and white decor. This unit sleeps ...
From $300 per night (USD)VRBO
From $125 per night (USD)HomeAway
Charming condo with No Car Needed and Bikes Included. Best location in town !
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
Walk or take your bikes everywhere from this little part of Paradise, you will never need a car. Located in beautiful O ...
From $125 per night (USD)HomeAway
From $125 per night (USD)VRBO
Tropical Escape in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Due to Covid 19, our unit is thoroughly sanitized after check-out. This luxurious condo/hotel features a wonderful trop ...
From $125 per night (USD)VRBO
From $207 per night (USD)HomeAway
Shady Nook @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Two blocks away from Duval Street with direct access to Thomas Street through the rear gate. Has free hook up for intern ...
From $207 per night (USD)HomeAway
From $225 per night (USD)VRBO
Tropical State of Mind Key West FL
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 5
Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition TV found in every bedroom in ...
From $225 per night (USD)VRBO