Key West Rentals
From $300 per night (USD)HomeAway
"BEACH HOUSE"~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
PRESTIGIOUS TROPICAL RETREAT... Indulge in this spectacular two-story home situated in the premier gated community of hi ...
From $300 per night (USD)HomeAway
From $200 per night (USD)VRBO
Charming Old Town Cottage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This charming conch home is newly renovated. Classic wood frame with Two bedrooms and Two baths on the first floor as we ...
From $200 per night (USD)VRBO
From $414 per night (USD)HomeAway
Sunset Dalite @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the breathtaking views of the Atlantic Ocean and the Gulf of Mexico from your front row seat! | This gorgeous cond ...
From $414 per night (USD)HomeAway
From $436 per night (USD)VRBO
**THE ZESTY LIME @ OLD TOWN** Beautifully Restored Home + 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 yo ...
From $436 per night (USD)VRBO
From $300 per night (USD)HomeAway
**SOUTHERNMOST PALMS @ THE ANNEX** Villa Near Duval & Beach + 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 yo ...
From $300 per night (USD)HomeAway
From $50 per night (USD)VRBO
Rose Lane Villas - Villa Alta - 1 bedroom - Sleeps 4 - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 wit ...
From $50 per night (USD)VRBO
Click For PricingHomeAway
10% off Available Dates Spring/Summer 2021
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
To provide our guests with a clean and sanitized home, our cleaning service cleans AND disinfects all high-touch surface ...
Click For PricingHomeAway
From $90 per night (USD)VRBO
Luxurious Historic House With Pool in Old Town INTRODUCTORY RATES! 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Monthly rental STUDIO with POOL just AVAILABLE. Same amenities. Save money if planing to come for over 14 days! Find it ...
From $90 per night (USD)VRBO
From $207 per night (USD)HomeAway
A Sunset View @ 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 $250 per night (USD)VRBO
"MOJITO DREAMIN" ~ Pet Friendly 3B/3Ba Condo Near Golf Course and Restaurants
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
WELL MANICURED COMMUNITY, SHORT DISTANCE FROM KEY WEST… Enjoy this modern, coastal inspired townhome that reflects the l ...
From $250 per night (USD)VRBO
From $480 per night (USD)HomeAway
SEAPORT SUNSETS at Galleon Resort in Old Town (Beach-Pool-BBQ)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING VIEWS OF KEY WEST HARBOR, SUNSET KE ...
From $480 per night (USD)HomeAway
From $749 per night (USD)VRBO
Oversized Oldtown home for the whole family with private pool and dock!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
"Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...
From $749 per night (USD)VRBO
From $250 per night (USD)HomeAway
Waterfront Home on Florida Bay with private heated pool in Key Cove Landings
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $250 per night (USD)HomeAway
From $240 per night (USD)VRBO
@@ New Ownerss many upgrades, Tropical retreat on the ocean@@
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located overlooking the tropical courtyard and garden area. Nicely decorated two bedroom two bath unit. Newly renovated ...
From $240 per night (USD)VRBO
From $207 per night (USD)HomeAway
Island Time @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $207 per night (USD)HomeAway
From $240 per night (USD)VRBO
**OCTOPUS'S GARDEN @ CORAL HAMMOCK** Spacious 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 yo ...
From $240 per night (USD)VRBO
From $250 per night (USD)HomeAway
Waterfront Home with private Pool & lush landscaping
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $250 per night (USD)HomeAway
From $207 per night (USD)VRBO
Aqua Oasis @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
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)VRBO
From $100 per night (USD)HomeAway
**SPLISH SPLASH @ THE GOLF CLUB** Sleek Home + LAST KEY SERVICES...
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $100 per night (USD)HomeAway
From $205 per night (USD)VRBO
Heavenly Hideaway-Monthly 2BD/21/2BA Private Pool Home
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
HEAVENLY HIDEAWAY! We are complying with the directives listed on the Monroe County website. Please be aware that info ...
From $205 per night (USD)VRBO
From $319 per night (USD)HomeAway
Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Location, location, location. Our spacious1800 Atlantic 3 bedroom condo offers a fabulous view of the ocean from all thr ...
From $319 per night (USD)HomeAway
Click For PricingVRBO
Key West Suites Hotel #205
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used t ...
Click For PricingVRBO
From $171 per night (USD)HomeAway
Marlin Blue @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Make your special trip to paradise most memorable with a stay in your bright and airy Shipyard Unit. Located within Trum ...
From $171 per night (USD)HomeAway
From $389 per night (USD)VRBO
**CASA FELIZ @ OLD TOWN** Historic Home & Pool | Near Duval + LAST KEY SERVICES.
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $389 per night (USD)VRBO
From $270 per night (USD)HomeAway
@ New Ownership, New Look, Ocean Hideaway Winter Savings Book now @
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Where the Ocean Meets the Windswept is nothing like You don't have to spend a fortune to enjoy a spacious, clean and c ...
From $270 per night (USD)HomeAway
From $279 per night (USD)VRBO
A Sunrise Cottage @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This charming 2 story 2 bedroom with loft, two bath cottage in the Shipyard Condominiums is located just off the pool an ...
From $279 per night (USD)VRBO
From $140 per night (USD)HomeAway
Sunset & Ocean View in Key West's Truman Annex, Bikes, Pool, Free WiFi & Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
We want to let you know that your safety and comfort is our priority. Past reviews have always praised how clean our con ...
From $140 per night (USD)HomeAway
From $394 per night (USD)VRBO
**SWEPT AWAY @ OLD TOWN** Dreamy Private Home & Jacuzzi + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $394 per night (USD)VRBO
From $328 per night (USD)HomeAway
**LA PROVENCE TROPICALE @ THE GOLF CLUB** Lavish Home + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $328 per night (USD)HomeAway
From $195 per night (USD)VRBO
**BOHEMIAN RHAPSODY @ CASA MARINA** Spacious Home / Pool + LAST KEY SERVICES...
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $195 per night (USD)VRBO
From $683 per night (USD)HomeAway
**MAISON TROPICALE @ OLD TOWN** Historic Home + 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 yo ...
From $683 per night (USD)HomeAway
From $495 per night (USD)VRBO
"CAPTAIN'S QUARTERS" ~ A Vintage Key West Retreat that is full of Charm!!
- Bedrooms:
- 3.5
- Bathrooms:
- 4
- Sleeps:
- 10
HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE Once you step through the threshold of this Old Town ...
From $495 per night (USD)VRBO
From $524 per night (USD)HomeAway
Luxury Waterfront home with elevator, private pool AND dock!
- Bedrooms:
- 4.5
- Bathrooms:
- 3
- Sleeps:
- 8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $524 per night (USD)HomeAway
From $393 per night (USD)VRBO
Luxury Waterfront at the Galleon Resort in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, ful ...
From $393 per night (USD)VRBO
From $223 per night (USD)HomeAway
**SUNSET POINT @ SUNSET MARINA** Condo / Pool & Spa + 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 yo ...
From $223 per night (USD)HomeAway
From $309 per night (USD)VRBO
CHARMING MONTHLY VACATION RENTAL
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Welcome to charming Studio Royale, a monthly Vacation Rental located in quirky Old Town Key West. Heated in ground pool. ...
From $309 per night (USD)VRBO
From $125 per night (USD)HomeAway
My Florida Escape: 2 BR, 2 BA Condominium in Key West, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You will love our piece of paradise. Our home away from home is tiled throughout. All new furnishings in 2017. Large fla ...
From $125 per night (USD)HomeAway
From $218 per night (USD)VRBO
**FOLLOW THE SUN @ THE BEACH** Ocean Condo / Pool & Tennis + 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 yo ...
From $218 per night (USD)VRBO
From $981 per night (USD)HomeAway
**SOUTHERNMOST HOSPITALITY VII** 7BR/7BA & Pool + LAST KEY SERVICES...
- Bedrooms:
- 8.5
- Bathrooms:
- 7
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $981 per night (USD)HomeAway
Click For PricingVRBO
Villa Mer at Shipyard Condominiums
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax at Villa Mer in luxurious surroundings. Renovated in 2019 it has a fully equipped kitchen with bar seating. The li ...
Click For PricingVRBO
From $90 per night (USD)HomeAway
Luxurious Historic House With Pool in Old Town 1 INTRODUCTORY RATES!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Monthly rental STUDIO with POOL just AVAILABLE. Same amenities. Save money if planing to come for over 14 days! Find it ...
From $90 per night (USD)HomeAway
From $218 per night (USD)VRBO
**LAYOVER in PARADISE @ CASA MARINA** New Home / Pool + 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 yo ...
From $218 per night (USD)VRBO
Click For PricingHomeAway
BEAUTIFULLY RENOVATED 3/5- 2 BLOCKS TO DUVAL, PRIVATE POOL, 2 CAR PARKING
- Bedrooms:
- 6
- Bathrooms:
- 3
- Sleeps:
- 8
**28-NIGHT MINIMUM PER CITY OF KEY WEST ORDINANCES** Fall in love with Key West while staying in our newly remodeled, g ...
Click For PricingHomeAway
From $378 per night (USD)VRBO
JASMINE PLACE - 1 blk to Duval - Private Pool - Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO JASMINE PLACE! We are complying with the directives listed on the Monroe County website. Please be aware th ...
From $378 per night (USD)VRBO
From $251 per night (USD)HomeAway
**VILLA MODERNA @ CASA MARINA** Sleek Home & 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 yo ...
From $251 per night (USD)HomeAway
From $500 per night (USD)VRBO
"ORCHID ESCAPE"~ 2 bedroom 2 bath set in Old Town with private dip pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
CLASSIC OLD KEY WEST HOME... This home is boasting a rare combination of location and character. A mix of historic detai ...
From $500 per night (USD)VRBO
From $83 per night (USD)HomeAway
It's a Salt Life After All @ the Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This 2 bedroom 2 bath town-home is just what you are looking for. *****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONL ...
From $83 per night (USD)HomeAway
From $215 per night (USD)VRBO
37 ft. Economy Boat In Downtown Key West Sailboat Perfect Small Charter Boat
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
Hurry pick your spring break dates we are filling up fast in Key West! This is the REAL Key West Experience. Our mari ...
From $215 per night (USD)VRBO
From $168 per night (USD)HomeAway
@@ Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret @@
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for compute ...
From $168 per night (USD)HomeAway
From $100 per night (USD)VRBO
Sea Breeze Cottage in Truman Annex Location! Location! Location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the beautiful Truman Annex. Get ready ...
From $100 per night (USD)VRBO
From $171 per night (USD)HomeAway
Annie's Hideaway @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This charming one bedroom, one bath 2nd floor property features an Olympic queen in the master bedroom and a large cover ...
From $171 per night (USD)HomeAway
From $300 per night (USD)VRBO
2 bdrm Condo w/ boat slip Pelican Landing Flamingo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
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)VRBO
From $500 per night (USD)HomeAway
Your Private Oasis in Old Town Key West - The Cigar Maker's Tropical Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Your tropical oasis in Historic Old Town Key West awaits for your monthly rental! 1890 Cigar Maker's Tropical Cottage re ...
From $500 per night (USD)HomeAway
From $245 per night (USD)VRBO
"THE QUARTERDECK" ~ Colorful & Comfortable 2Ba/ 1Ba Unit in The Shipyard!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
COMFORT AND VALUE IN TRUMAN ANNEX… This newly renovated two bedroom condo is located in The Shipyard, a neighborhood of ...
From $245 per night (USD)VRBO
From $125 per night (USD)HomeAway
@ Beautifully renovated Condo on the Ocean Available Feb & March 20201 @
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Garden View. 2 bedroom 2 full bathrooms, sleeps a max of 6. Luxurious tropical courtyard view two bedroom condo. This e ...
From $125 per night (USD)HomeAway
From $273 per night (USD)VRBO
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $273 per night (USD)VRBO
Click For PricingHomeAway
Old Town Charm Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This charming Old Town cottage is a short walk to Duval Street nightlife, restaurants, shops and culture… and a walk or ...
Click For PricingHomeAway
From $225 per night (USD)VRBO
@@ Fantastic Spring& Summer Stay Downtown walk everywhere @@
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilt ...
From $225 per night (USD)VRBO
From $79 per night (USD)HomeAway
Villa Fleur at Shipyard Condominiums
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax at Villa Fleur in luxurious surroundings. Renovated in 2018 it has a fully equipped kitchen with bar seating and d ...
From $79 per night (USD)HomeAway
From $193 per night (USD)VRBO
"IN GOOD SPIRITS"~Waterfront Condo w/Wrap-Around Balcony & Community Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
BEACHES ON BOTH SIDES... This two bedroom condo is close to the airport, beaches, restaurants and minutes away from Duva ...
From $193 per night (USD)VRBO
From $202 per night (USD)HomeAway
**BLUE HERON'S COVE @ THE ANNEX** Luxury Villa by Duval + 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 yo ...
From $202 per night (USD)HomeAway
From $207 per night (USD)VRBO
Another Three Hour Tour @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
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)VRBO
From $134 per night (USD)HomeAway
@Atlantic Docks Fantastic Ocean View Condo- Short bike ride to Old Town@
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1800 Atlantic Condominiums Unit C433 2 Bedroom 2 full baths Elegant sophistication abound in this fabulous 2 bedroom 2 ...
From $134 per night (USD)HomeAway
From $599 per night (USD)VRBO
Spacious Luxury Waterfront Home with Elevator, Pool and Private Dock!
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $599 per night (USD)VRBO
From $496 per night (USD)HomeAway
**SEVENTH HEAVEN @ THE ANNEX** Elegant Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $496 per night (USD)HomeAway
From $1195 per night (USD)VRBO
"THE SEASHELL" ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
CLASSIC KEY When only the best will do! The Seashell is the classic Old Town Key West home. Perfect setting for your dr ...
From $1195 per night (USD)VRBO
From $168 per night (USD)HomeAway
**BIRD of PARADISE** Elegant Home & 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 yo ...
From $168 per night (USD)HomeAway
From $517 per night (USD)VRBO
A Love Shack in the Keys!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Fully furnished cottage home in the heart of old town key west. This place is perfect for a couple as the house is small ...
From $517 per night (USD)VRBO
From $214 per night (USD)HomeAway
2 Bedroom 1 Bathroom in Shipyard at Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
7 night minimum rental. Paradise is definitely found in this Non-Smoking, first floor condo only two short blocks off of ...
From $214 per night (USD)HomeAway
From $89 per night (USD)VRBO
“STONE'S THROW” ~ 2 Bedroom Cottage with Shared Pool, its a PERFECT LOCATION!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CLOSE TO THE This Adorable Conch Cottage is a “Stone’s Throw” from everything that Key West has to offer! Literally st ...
From $89 per night (USD)VRBO
From $293 per night (USD)HomeAway
A Mangrove Snapper @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This charming getaway in the prestigious Porter Court is located in the award winning Truman Annex in Old Town Key West. ...
From $293 per night (USD)HomeAway
From $95 per night (USD)VRBO
View View View best describes our newly furnished 2 bedroom 2 bath condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
our 2 bedroom 2 bath unit has a beautiful view of the Atlantic ocean and Smathers beach from our living & dining room, f ...
From $95 per night (USD)VRBO
From $414 per night (USD)HomeAway
Driftwood Buoy @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
A luxury, ocean front, 2 bedroom, (king in master, twins or twins as king in guest bedroom, queen sleeper in living room ...
From $414 per night (USD)HomeAway
From $321 per night (USD)VRBO
Spacious Waterfront 4 Bedroom Home With Private Heated Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
If you’re looking for an upscale escape by the sea, Havana Daydream is your Key West hidden gem. Enjoy the island life i ...
From $321 per night (USD)VRBO
From $50 per night (USD)HomeAway
Rose Lane Villas - Villa Vista - 2 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 $245 per night (USD)VRBO
"ATLANTIC BREEZE" ~ 2B/2BA Tropical Retreat w/ Pool, Fitness Area & Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
BEACHES ON BOTH SIDES... This two bedroom condo is close to the airport, beaches, restaurants and minutes away from Duva ...
From $245 per night (USD)VRBO
From $443 per night (USD)HomeAway
The Plantation @ the Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
‘The Plantation” is a Three Bedroom Town home located within the prestigious gated community of ‘Truman Annex’ in Key We ...
From $443 per night (USD)HomeAway
From $150 per night (USD)HomeAway
Cool Breeze @ the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cool Breeze at the Key West Golf Club-*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY.***** | This community is ...
From $150 per night (USD)HomeAway
From $233 per night (USD)VRBO
A Bella Capri @ the Beach
- Bedrooms:
- 4.5
- Bathrooms:
- 5
- Sleeps:
- 10
This magnificent 5 bedroom Mediterranean villa has a landmark presence, complete privacy and a breathtaking outdoor plaz ...
From $233 per night (USD)VRBO
From $207 per night (USD)HomeAway
Tropical Breezes @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
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 $208 per night (USD)VRBO
Sail Boat Catamaran / House Boat/ Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
As you starting reading about my boat, I would like to tell you what we doing to protect traveling public from Covid-1 ...
From $208 per night (USD)VRBO
From $100 per night (USD)HomeAway
Truman Annex Condo, Close to Beach & Duval with 2 Bikes, Upper level, Free WIFI!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A TRUE CARIBBEAN PARADISE! Location! Location! Location! The Conch Retreat Condo is located in the Beautiful Shipyard of ...
From $100 per night (USD)HomeAway
From $271 per night (USD)VRBO
Alegre @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in picturesque Truman Annex in fabulous, sunny Key West, Alegre is close to all the fun and activities yet quiet ...
From $271 per night (USD)VRBO
From $171 per night (USD)HomeAway
Oyster's Pearl @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This 1BR 1BA condo has an extra large living room with a big screen TV. It sits nestled in the back of the Shipyard back ...
From $171 per night (USD)HomeAway
From $125 per night (USD)VRBO
@Free Island Spirit Key West March 2020 $5500 Monthly plus fees @@
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Lovely 3rd floor interior courtyard view monthly rental. Enjoy the serenity of this bright and airy unit. This unit offe ...
From $125 per night (USD)VRBO
From $343 per night (USD)HomeAway
Forever Young @ Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breath taking water ...
From $343 per night (USD)HomeAway
From $207 per night (USD)VRBO
About Time @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $207 per night (USD)VRBO
From $414 per night (USD)HomeAway
Aqua Breeze @ 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 $714 per night (USD)VRBO
"SOUTHERNMOST BELLE"~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
LUXURY IN OLD TOWN... Grand home in the Historic Seaport area of Old Town Key West. Tucked behind a canopy of palms this ...
From $714 per night (USD)VRBO
From $327 per night (USD)HomeAway
**WINDSWEPT PALMS @ THE BEACH** Oceanfront / Pool & Jacuzzi + 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 yo ...
From $327 per night (USD)HomeAway
From $89 per night (USD)VRBO
Downtown, Affordable & Clean available Winter of 2021- Extended stay discount
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar ...
From $89 per night (USD)VRBO
From $268 per night (USD)HomeAway
@ Amazing Ocean Front 3 Bedroom Open Winter of 2022 @
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride ...
From $268 per night (USD)HomeAway
From $234 per night (USD)VRBO
Peaceful Setting Amongst The Active Island Life Style
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the New and Completely Renovated bathrooms to this tropical residence. This is quiet, peaceful living on the Atlan ...
From $234 per night (USD)VRBO
From $236 per night (USD)HomeAway
A Sunset Poolside @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This amazing FIRST FLOOR end unit features two bedrooms and TWO ensuite bathrooms with walk in showers. Each bedroom has ...
From $236 per night (USD)HomeAway
From $218 per night (USD)VRBO
**SOUTHERN STAR @ THE MEADOWS** 4BR Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 4.5
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $218 per night (USD)VRBO
From $171 per night (USD)HomeAway
SPECTACULAR PRICE :) Tropical Vineyard @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
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 $300 per night (USD)VRBO
2 bdrm Condo w/ boat slip Pelican Landing Andros
- 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)VRBO
From $207 per night (USD)HomeAway
Blue Heaven @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
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 $872 per night (USD)VRBO
**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $872 per night (USD)VRBO
From $175 per night (USD)HomeAway
Beach Chic w a Waterfront Park View
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Please call or text if you’d like to book our home 702 232... 3750 When booking our home please include a brief descri ...
From $175 per night (USD)HomeAway
From $487 per night (USD)VRBO
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $487 per night (USD)VRBO
From $643 per night (USD)HomeAway
!!LADY EMMA!! BEAUTY!! VERY PRIVATE!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Lady Emma which is located in the best location in Old Town, the world famous Truman Annex on Emma St. The Tr ...
From $643 per night (USD)HomeAway
From $189 per night (USD)VRBO
**HEART of the HARBOR @ THE SEAPORT** Old Town Living & Pool + 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 yo ...
From $189 per night (USD)VRBO
From $436 per night (USD)HomeAway
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + 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 yo ...
From $436 per night (USD)HomeAway
From $545 per night (USD)VRBO
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $545 per night (USD)VRBO
From $171 per night (USD)HomeAway
Sand Crab Cabana @ 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 $200 per night (USD)VRBO
Old Town Key West - Historic & Charming - 2 Blks From Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
A few words about the 'damn'pandemic… The health and safety of our guests and employees is our top priority. Our homes ...
From $200 per night (USD)VRBO
From $545 per night (USD)HomeAway
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $545 per night (USD)HomeAway
From $257 per night (USD)VRBO
Green Bamboo @ the Truman Annex
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to Paradise! This 2 bedroom townhouse, one bedroom is a king and the second bedroom features twin beds which can ...
From $257 per night (USD)VRBO
From $349 per night (USD)HomeAway
KEY WEST LIVIN' Beautiful 50' Yacht with 3 Bed, 2 Bath sleeps 6.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
SAFER THEN ANY HOTEL IN KEY WEST PRIVATE AND SECLUDED ACCOMMODATION. We are The safest option for travel to Key West ...
From $349 per night (USD)HomeAway
From $291 per night (USD)VRBO
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 8
- Bathrooms:
- 5
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $291 per night (USD)VRBO
From $531 per night (USD)HomeAway
**THE ADMIRAL'S ESTATE** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6.5
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $531 per night (USD)HomeAway
From $550 per night (USD)VRBO
**COASTAL CABANA @ LOVE LANE** Cul-de-Sac Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $550 per night (USD)VRBO
From $184 per night (USD)HomeAway
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $184 per night (USD)HomeAway
From $240 per night (USD)VRBO
Fall Specials Enchanting garden view on the Ocean Great Rates @@
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
1st floor garden-view unit, King in the master bedroom, A double and a single in the guest bedroom and a queen sleeper ...
From $240 per night (USD)VRBO
From $279 per night (USD)HomeAway
Amberjack @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gate ...
From $279 per night (USD)HomeAway
From $294 per night (USD)VRBO
**CIELO AZUL @ THE BEACH CLUB** Oceanfront Condo / Pools + 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 yo ...
From $294 per night (USD)VRBO
From $446 per night (USD)HomeAway
**THE POLYNESIAN HOUSE @ CASA MARINA** Estate & Huge Pool + LAST KEY SERVICES...
- Bedrooms:
- 5.5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $446 per night (USD)HomeAway
From $240 per night (USD)VRBO
Poolside Breeze Retreat A103: 2 BR, 2 BA Condominium in Key West, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Poolside Breeze is a nicely decorated two bedroom 1st floor condominium with an excellent location very close to the poo ...
From $240 per night (USD)VRBO
Click For PricingHomeAway
PEAK OF DUVAL: Sophisticated Bright & Breezy Duval Street Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
Click For PricingHomeAway
From $545 per night (USD)VRBO
"STRIPES" ~ Delightful Condo Located in the Heart of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key ...
From $545 per night (USD)VRBO
From $273 per night (USD)HomeAway
**2 COOL FISH @ THE ANNEX** Chic Villa + Pool + LAST KEY SERVICES…
- Bedrooms:
- 2.5
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $273 per night (USD)HomeAway
From $207 per night (USD)VRBO
Manatee @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
'Manatee' is a beautiful two bedroom, one bath, 1st floor condominium located within the prestigious gated community of ...
From $207 per night (USD)VRBO
From $150 per night (USD)HomeAway
Closer to Cuba than Walmart - Blu
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West. This nightly rental i ...
From $150 per night (USD)HomeAway
From $995 per night (USD)VRBO
"SEAHORSE COVE" ~ Tropical Luxury Located In The Heart Of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...
From $995 per night (USD)VRBO
From $467 per night (USD)HomeAway
**CASA SUITE CASA @ CASA MARINA** Lush Home / Pool + LAST KEY SERVICE...
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $467 per night (USD)HomeAway
From $59 per night (USD)VRBO
The Galleon Resort Best Resort Location in KW
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This October condo is a 2BR, 2BA sunset/pool view sleeps 6. Condo has a full modern kitchen with granite/stainless, di ...
From $59 per night (USD)VRBO
From $322 per night (USD)HomeAway
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + 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 yo ...
From $322 per night (USD)HomeAway
From $207 per night (USD)VRBO
Almost Paradise @ the Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
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)VRBO
From $614 per night (USD)HomeAway
Catch of the Day @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
View passing ships and sunsets from your own deck or balcony in the Truman Annex's most prestigious building, the former ...
From $614 per night (USD)HomeAway
Click For PricingVRBO
Discounted April spacious 2 BR second floor apartment in historic Conch home!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Beautiful large 2 bedroom, 1 bath second floor apartment with high ceilings and beautifully decorated. Near beaches and ...
Click For PricingVRBO
Click For PricingHomeAway
LAST MINUTE OFFER! 44' Sailing Yacht & Other Boats
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 9
You will have this one of a kind, yacht all to yourself! This yacht has a large great room and kitchen area with window ...
Click For PricingHomeAway
From $171 per night (USD)VRBO
A Pleasant Stay @ 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)VRBO
From $571 per night (USD)HomeAway
Beautiful Large home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a beautiful private home located in the Historic Truman Gated Community Old Town Key West. Only steps away from Du ...
From $571 per night (USD)HomeAway
From $345 per night (USD)VRBO
"OFF CALL" ~ Rustic, Nautical Decor With King Master Suite & Heated Pool!
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 6
GATED COMMUNITY CLOSE TO BOATING AND GOLFING... “OFF CALL” is a beautiful townhome in the Coral Hammock community; total ...
From $345 per night (USD)VRBO
From $170 per night (USD)HomeAway
**SUZY'S PARROT PERCH @ OLD TOWN** Cozy 2nd Floor Condo + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $170 per night (USD)HomeAway
From $300 per night (USD)VRBO
**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & 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 yo ...
From $300 per night (USD)VRBO
From $1363 per night (USD)HomeAway
**AVALYNN HOUSE @ THE ANNEX** Lush Home by Beach & Duval + LAST KEY SERVICES...
- Bedrooms:
- 4.5
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $1363 per night (USD)HomeAway
From $236 per night (USD)VRBO
Gracie Bay's Hideaway @ The Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Thank you for considering Gracie Bay’s Hideaway for your escape to the tropical paradise of Key West. Here you will enjo ...
From $236 per night (USD)VRBO
From $117 per night (USD)HomeAway
30 night Minimum Stay Heart of Historic downtown 214 2 bed 2 1/2 Bath
- Bedrooms:
- 3.5
- Bathrooms:
- 2
- Sleeps:
- 4
This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps ...
From $117 per night (USD)HomeAway
From $281 per night (USD)VRBO
**CAYO CALYPSO @ HIGGS BEACH** Modern 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 yo ...
From $281 per night (USD)VRBO
From $279 per night (USD)HomeAway
Archipelago l @ the Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Presidents Walk and Southard Court community is located in the Truman Annex Complex which is located 2 blocks from D ...
From $279 per night (USD)HomeAway
From $228 per night (USD)VRBO
"CASA DE VINO" ~ Amazing Price for Charming Townhouse with Pool & Tiki!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
GATED COMMUNITY, CLOSE TO BOATING AND GOLFING... Casa de Vino, in the Coral Hammock Community is a gorgeous three bedroo ...
From $228 per night (USD)VRBO
From $300 per night (USD)HomeAway
NEW UNIT!!! GORGEOUS!! Island Oasis @ Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. | The living area is the ent ...
From $300 per night (USD)HomeAway
From $405 per night (USD)VRBO
Tiki BeachToo! 2 blocks to Duval, pool, grill, bikes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Tiki Beach Too is a Newly Renovated, 2 bedroom/2bathroom, charming town home in enchanting Truman Annex, in the heart of ...
From $405 per night (USD)VRBO
From $104 per night (USD)HomeAway
**COCONUT** Old Town! Adorable!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The 'Coconut' as it's so lovingly referred to is the perfect Pied A Terre for your vacation in the Florida Keys. Open l ...
From $104 per night (USD)HomeAway
From $218 per night (USD)VRBO
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to yo ...
From $218 per night (USD)VRBO
From $218 per night (USD)HomeAway
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach 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 yo ...
From $218 per night (USD)HomeAway
From $382 per night (USD)VRBO
**THE SMILING IBIS @ 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 yo ...
From $382 per night (USD)VRBO
From $507 per night (USD)HomeAway
"LADY ADMIRAL" ~ Sweet cottage & guest house with private pool off Duval
- Bedrooms:
- 3.5
- Bathrooms:
- 3
- Sleeps:
- 8
A SWEET SURPRISE JUST OFF DUVAL... Private single family home with off street parking totaling three bedrooms, two and h ...
From $507 per night (USD)HomeAway