Key West Rentals
From $874 per night (USD)HomeAway
Architects Cottage in fantastic Old Town location!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
We have a wonderful MONTHLY rental to offer you: an historic 'conch' house has been completely redesigned and custom cra ...
From $874 per night (USD)HomeAway
From $370 per night (USD)VRBO
Villa Nouveau Key West ~ Fabulous downtown Key West location just off-Duval St.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sometimes a Key West cottage that at first glance appears predictable from the outside, is full of abundant surprises wh ...
From $370 per night (USD)VRBO
From $190 per night (USD)HomeAway
Parrot Perch by AT HOME IN KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Unbeatable location at a great price! The Parrot Perch is in the gated Shipyard Community of the prestigious Truman Anne ...
From $190 per night (USD)HomeAway
From $45 per night (USD)VRBO
Truman Annex unit 254
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Key Lime has a large open kitchen, vaulted ceilings and tile floors throughout. This immaculate unit has two-bedrooms, 2 ...
From $45 per night (USD)VRBO
From $150 per night (USD)HomeAway
Serenity at La Brisa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
If you wish to escape from the world of anxiety and pressure, Serenity is the home for you. Our unique view of the Salt ...
From $150 per night (USD)HomeAway
From $80 per night (USD)VRBO
~POPPY COTTAGE~ Cute Home In Quiet Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
About THE PROPERTY: Can you say “perfectly adorable”? We thought so. Now picture “perfectly adorable” and you have fou ...
From $80 per night (USD)VRBO
From $100 per night (USD)HomeAway
Fishing Paradise @ Sunset Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Sports Fishing Paradise has everything you could want in a home away from home. It is close to Old Town so you can still ...
From $100 per night (USD)HomeAway
From $75 per night (USD)VRBO
The Caribbean Suite - 2-K-bedroom / 1 bath / kitchenette / sleeps up to 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This deluxe "Key West Charmer" is a beautifully restored Victorian home built in the 1880's that was converted into indi ...
From $75 per night (USD)VRBO
From $475 per night (USD)HomeAway
Royal Escape- 3BR/3BA, W/ Private Pool In Casa Marina Area-
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
If Cleopatra and Anthony had dreamed of a Key West hideaway this spacious three bedroom, three bath “Royal Escape” would ...
From $475 per night (USD)HomeAway
From $190 per night (USD)VRBO
Breezy Bungalow by AT HOME IN KEY WEST
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you! When a name says it all you ...
From $190 per night (USD)VRBO
From $150 per night (USD)HomeAway
Fall Special in Truman Annex, two blocks from Duval
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Available for weekly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful ...
From $150 per night (USD)HomeAway
From $225 per night (USD)VRBO
Ashe Splashe: A beautiful restoration of a historic Key West property
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
28 DAY MINIMUM RENTAL From the owners of South of Frances, here is another beautiful, historic restoration project. Th ...
From $225 per night (USD)VRBO
From $300 per night (USD)HomeAway
Located in Old Town, AMELIA HOME offers private pool; PET FRIENDLY PROPERTY!
- Bedrooms:
- 4.5
- Bathrooms:
- 2
- Sleeps:
- 6
After a long day cool off in your private pool, enjoy cold Mojitos on the covered porch and cook up some fresh grouper o ...
From $300 per night (USD)HomeAway
From $329 per night (USD)VRBO
KW GULF FRONT/Gulf view Home with dock and pool.
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
On the entire island of Key West there are fewer than 50 private homes on open water and only a few with their own priva ...
From $329 per night (USD)VRBO
From $215 per night (USD)HomeAway
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)HomeAway
From $186 per night (USD)VRBO
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)VRBO
From $579 per night (USD)HomeAway
Key West Wabi Sabi ~ 1/2 Block Off Duval. Undeniable Adorable Authentic Pool.
- 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)HomeAway
From $370 per night (USD)VRBO
Heavenly Hideout at Key West Mile Zero ~ Mallory Square only 3 Blocks Away!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both ...
From $370 per night (USD)VRBO
From $165 per night (USD)HomeAway
Conch Get Enough! - Old Town's Truman Annex
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy an early morning cup of coffee on your private bedroom balcony after being gently woken by the crowing of a wild r ...
From $165 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 $1534 per night (USD)HomeAway
Bella Grand Premier ~ Superbly Renovated Victorian Estate at Historic Seaport
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Classic romantic 1800’s Key West architecture has inspired a superbly executed renovation of this extraordinary historic ...
From $1534 per night (USD)HomeAway
From $325 per night (USD)VRBO
Downtown Cottage just off famous Duval Street
- 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)VRBO
From $329 per night (USD)HomeAway
"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)HomeAway
From $300 per night (USD)VRBO
By The Beautiful Sea ~ Ocean View At The Beach Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
If you’re craving a Key West beach accommodation with a bone fide front-line view to the sea, you know they’re not easy ...
From $300 per night (USD)VRBO
From $520 per night (USD)HomeAway
Amelia's Hideaway ~ Hidden Courtyard Villa with Private Pool
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 10
"In-the-know" travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as th ...
From $520 per night (USD)HomeAway
From $484 per night (USD)VRBO
Key West Dreamin' ~ Downtown Location Near Duval Street with a Private Pool
- 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)VRBO
From $264 per night (USD)HomeAway
Fairway to Heaven at the KW Golf Club
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 6
Fairway to Heaven is a newly furnished and decorated bungalow, ideally located at the beautiful 18 hole Key West Golf Cl ...
From $264 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 $225 per night (USD)VRBO
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)VRBO
From $329 per night (USD)HomeAway
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)HomeAway
From $230 per night (USD)VRBO
Enjoy private hot tub at KEY WEST GINGER HOUSE. YOUR FIDO IS WELCOME TOO!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located right around the corner from Banana Cafe and Duval Street ,but still offering plenty of privacy, this cozy cotta ...
From $230 per night (USD)VRBO
From $1000 per night (USD)HomeAway
Southernmost Point in USA
- 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 $325 per night (USD)VRBO
Caribbean Cottage ~ Duval Street Key West Caribbean Cottage With Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian s ...
From $325 per night (USD)VRBO
From $325 per night (USD)HomeAway
Elegant Key West Tree House ~ Overlooks Historic Tropical Tree Garden
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, ...
From $325 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 $250 per night (USD)HomeAway
Island Time Key West Monthly Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Elegance and modern sophistication are apparent as you enter this luxurious home conveniently located in a quiet Old To ...
From $250 per night (USD)HomeAway
From $140 per night (USD)VRBO
~ 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)VRBO
From $200 per night (USD)HomeAway
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)HomeAway
From $300 per night (USD)VRBO
Dancing Palms Villa ~ Hidden in the Heart of Old Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant st ...
From $300 per night (USD)VRBO
From $225 per night (USD)HomeAway
Vista Fresco : Oceanside condominiums with resort-style amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors ...
From $225 per night (USD)HomeAway
From $1000 per night (USD)VRBO
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)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 offers walking distance to historic sites, restaurants, nightlife and the beach.
- 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 get-a-way vacation rental for those seeking a good time, but would like ...
From $148 per night (USD)VRBO
From $110 per night (USD)HomeAway
Private & Peaceful Cottage Feel, Discounted Rates 50$ off
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
GREAT LOCATION AND GREAT VALUE! The rates posted are incredibly reasonable, considering what you are getting. My plac ...
From $110 per night (USD)HomeAway
From $265 per night (USD)VRBO
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)VRBO
From $275 per night (USD)HomeAway
New Beach Club unit - Freshly decorated
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
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 $45 per night (USD)VRBO
Truman Annex unit202-3
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Truman Annex unit202-3 This upstairs unit has beautiful views and offers a private front and back porch. There is a quee ...
From $45 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 $85 per night (USD)HomeAway
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)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
- 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:
- 5
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/ 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 $59 per night (USD)VRBO
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)VRBO
From $500 per night (USD)HomeAway
The Hamilton House in old town Key West
- Bedrooms:
- 5.5
- Bathrooms:
- 5
- Sleeps:
- 9
Monthly Rentals only. Minimum 28 days.Steps away from the Southernmost point and Duval street. This single family home o ...
From $500 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: Welcome to Steamplant 207! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key Wes ...
From $240 per night (USD)VRBO
From $329 per night (USD)HomeAway
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)HomeAway
From $100 per night (USD)VRBO
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)VRBO
From $126 per night (USD)HomeAway
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)HomeAway
From $150 per night (USD)VRBO
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)VRBO
From $55 per night (USD)HomeAway
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)HomeAway
From $500 per night (USD)VRBO
Casa Loca- One of a kind estate 1/2 block from Duval in Old Town Key West
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Loca ---Experience the uniqueness of Key West by staying at one of Key West Hideaways one of a kind vacation rent ...
From $500 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:
- 6
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 $125 per night (USD)VRBO
Historic District-Great Location-Pool View-Beach Nearby-Gated Community
- 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 $70 per night (USD)HomeAway
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)HomeAway
From $809 per night (USD)VRBO
Grande Dame Key West ~ This award winning renovation of a 3 - story Estate
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
Grande Dame Key West – (The Watson House) vacation rental estate is an impeccably detailed 3-story Classic Folk Victoria ...
From $809 per night (USD)VRBO
From $275 per night (USD)HomeAway
Luxury 2 Bedroom 2.5 Bath Townhouse on Duval Street. Great Location
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Located just steps from famous Duval street, this two-story town home is located in quaint, cobble stoned Duval Square. ...
From $275 per night (USD)HomeAway
From $100 per night (USD)VRBO
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)VRBO
From $200 per night (USD)HomeAway
Spectacuar views of Smather's Beach and the Atlantic Ocean
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Our Home Away from Home! NEW - all kitchen appliances, new pillow top mattresses in both bedrooms, 46' flat p ...
From $200 per night (USD)HomeAway
From $751 per night (USD)VRBO
~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)VRBO
From $295 per night (USD)HomeAway
Catherine House: A charming Old Town Key West cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming Key West style cottage is just a short walk to a selection of great restaurants, art galleries, and shoppi ...
From $295 per night (USD)HomeAway
From $150 per night (USD)VRBO
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)VRBO
From $59 per night (USD)HomeAway
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)HomeAway
From $85 per night (USD)VRBO
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)VRBO
From $150 per night (USD)HomeAway
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)HomeAway
From $200 per night (USD)VRBO
Craig & Cindy Key West 2 Bedroom Beachside Resort Condo
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
Our luxurious condo is part of the spectacular Beachside Resort & Conference Center. Beachside is Key West and South Fl ...
From $200 per night (USD)VRBO
From $520 per night (USD)HomeAway
Villa Déjà vu Key West ~ Private pool & garden located just off Upper Duval.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
You know that incredible experience of Déjà vu? When you enter someplace for the very first time, and instantly you get ...
From $520 per night (USD)HomeAway
From $229 per night (USD)VRBO
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)VRBO
From $275 per night (USD)HomeAway
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)HomeAway
From $260 per night (USD)VRBO
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)VRBO
From $225 per night (USD)HomeAway
Truman's Hideaway by AT HOME IN KEY WEST
- 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)HomeAway
From $163 per night (USD)VRBO
~ BESS TRUMAN SUITE ~ Perfect Suite w/ Heated PooI Just Steps to Duval St!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
About THE PROPERTY: Bess Truman Suite is steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restauran ...
From $163 per night (USD)VRBO
From $249 per night (USD)TripAdvisor
Center of It All - Paradise Island Suite
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duva ...
From $249 per night (USD)TripAdvisor
From $162 per night (USD)PerfectPlaces
Wind Swept
- Bedrooms:
- 1.5
- Bathrooms:
- 2
- Sleeps:
- 6
Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the on ...
From $162 per night (USD)PerfectPlaces