Key West Rentals
- From $457 per night (USD)
VRBO
A LICENSE TO CHILL at the Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
The historic Foundry, known as building #11, features three story townhomes, located in the award-winning residential ne ...
From $457 per night (USD)VRBO
- From $1060 per night (USD)
Expedia
**BAHAMIAN BLUES @ BAHAMA VILLAGE** Impeccable Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! BAHAMIAN BLUE ...
From $1060 per night (USD)Expedia
- From $340 per night (USD)
VRBO
PELICAN - A cheerful condo in beautiful Truman Annex and close to Duval St.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
When choosing your dates, please keep in mind that we rent a minimum of 7 DAYS from SATURDAY to SATURDAY. (One exception ...
From $340 per night (USD)VRBO
- From $245 per night (USD)
Expedia
Quaint Island Escape Condo w\/Spacious Balcony Deck in Beautiful Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This lovely Island Escape Condo is a upper level condo located in the prestigious Truman Annex. Not just another rental ...
From $245 per night (USD)Expedia
- From $1029 per night (USD)
VRBO
DOLPHIN WATCH in Key West @ The Truman Annex Compass Realty
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attrac ...
From $1029 per night (USD)VRBO
- From $379 per night (USD)
Expedia
AMBERJACK at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gate ...
From $379 per night (USD)Expedia
- From $821 per night (USD)
VRBO
CATCH OF THE DAY at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
View passing ships and sunsets from your own first floor, large deck with plenty of seating for a large family in the Tr ...
From $821 per night (USD)VRBO
- From $364 per night (USD)
Expedia
SOUTHARD COMFORT at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
LOCATION, LOCATION, LOCATION! Southard Comfort is on Southard Street in the TRUMAN ANNEX, which is one of the most beau ...
From $364 per night (USD)Expedia
- From $131 per night (USD)
VRBO
Colorful cottage w\/shared pool, central AC, washer\/dryer
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Grinnell Street Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $131 per night (USD)VRBO
- From $675 per night (USD)
Expedia
Luxury Waterfront at Galion Resort in Old Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $675 per night (USD)Expedia
- From $333 per night (USD)
VRBO
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! DOCKSIDE DAYD ...
From $333 per night (USD)VRBO
- From $645 per night (USD)
Expedia
Sunnyside Up by Brightwild | Pool & Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
Summary: This charming Key West conch home is situated on United Street, on the edge of "Old Town" Key West. The kitchen ...
From $645 per night (USD)Expedia
- From $165 per night (USD)
VRBO
South Beachside at 1800 Atlantic by Smathers Beach & 10 minute bike Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully renovated 2 bedroom 2 bath ocean view Condo at 1800 Atlantic. Fabulous layout where both bedrooms and the li ...
From $165 per night (USD)VRBO
- Click For Pricing
VRBO
Lovely 2 bedroom, 2 bathroom steps from the beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Key West at La Brisa, a gated Condo community, just steps from the beach on Key West's Atlantic coast. Walk in ...
Click For PricingVRBO
- From $586 per night (USD)
VRBO
PARADISE ON THE OCEANat The Truman Annex in Key West
- Bedrooms:
- 3
- 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 $586 per night (USD)VRBO
- From $379 per night (USD)
Expedia
A SUNRISE COTTAGE at The Truman Annex in Key West
- 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 $379 per night (USD)Expedia
- From $356 per night (USD)
VRBO
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "Cocktails & Dreams," an impeccably updated second-floor condo located in the coveted Shipyard Condominiums. ...
From $356 per night (USD)VRBO
- From $336 per night (USD)
Expedia
ALMOST PARADISE at The Truman Annex in Key West
- 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 $336 per night (USD)Expedia
- From $1638 per night (USD)
VRBO
The Curry House by Brightwild | Historic Guesthome
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 18
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $1638 per night (USD)VRBO
- From $203 per night (USD)
Expedia
Curry House #6 by Brightwild | King Bed, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic conch house charm that take you back in time. This guest ...
From $203 per night (USD)Expedia
- From $339 per night (USD)
VRBO
Curry House by Brightwild | Balcony & Pool -Rm 3&4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $339 per night (USD)VRBO
- From $216 per night (USD)
Expedia
Curry House Room 1 | Heated Pool & Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic conch house charm that take you back in time. This guesth ...
From $216 per night (USD)Expedia
- From $230 per night (USD)
VRBO
Curry House #8 by Brightwild | King Bed, Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $230 per night (USD)VRBO
- From $203 per night (USD)
Expedia
Curry House #7 by Brightwild | King Bed, Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $203 per night (USD)Expedia
- From $185 per night (USD)
VRBO
Curry House #2 by Brightwild | Balcony & Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $185 per night (USD)VRBO
- From $211 per night (USD)
Expedia
Curry House by Brightwild | Heated Pool - Rm #9
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $211 per night (USD)Expedia
- From $240 per night (USD)
VRBO
Curry House Room 5 | King Bed, 1st Floor
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: "Curry House" provides three stories full of historic charm that take you back in time. This guesthouse has pr ...
From $240 per night (USD)VRBO
- From $165 per night (USD)
Expedia
**PAINTED SKY @ SUNSET MARINA** Waterfront Condo & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! With a backdr ...
From $165 per night (USD)Expedia
- From $494 per night (USD)
VRBO
Sweet Caroline by Brightwild | Pool & Parking
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $494 per night (USD)VRBO
- From $228 per night (USD)
Expedia
Key Lime Cottage by Brightwild | Pool & Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $228 per night (USD)Expedia
- From $214 per night (USD)
VRBO
Sugar Pie Suite by Brightwild | Pool & Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $214 per night (USD)VRBO
- From $190 per night (USD)
Expedia
Honey Bun Hideaway by Brightwild | Pool & Grill!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $190 per night (USD)Expedia
- From $244 per night (USD)
VRBO
Banana Split by Brightwild | Pool & Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $244 per night (USD)VRBO
- From $209 per night (USD)
Expedia
Creme Brulee Suite by Brightwild | Pool & Grill
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Banana's Foster Guest House is a charming, historic home situated in the heart of Key West. This unique old con ...
From $209 per night (USD)Expedia
- From $1014 per night (USD)
VRBO
Villa Déjà vu Key West
- 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 $1014 per night (USD)VRBO
- From $429 per night (USD)
Expedia
COLORFUL COCKTAIL at The Truman Annex in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This Shipyard unit is a two level condominium which has a private courtyard with a deck to enjoy the beautiful weather a ...
From $429 per night (USD)Expedia
- From $733 per night (USD)
VRBO
**BANANA BLOSSOMS @ THE ANNEX** Lush Villa by Beach + Pool + LAST KEY SERVICES
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! When explorin ...
From $733 per night (USD)VRBO
- From $557 per night (USD)
Expedia
A PALM OASIS at The Truman Annex in Key West.....
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
NEW LISTING!!! This charming two bedroom, two and one half bath townhome has recently been updated and added to our rent ...
From $557 per night (USD)Expedia
- From $258 per night (USD)
VRBO
Coastal Inspired Cottage in Bahama Village Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Bahama Dreams, a fully renovated 3 bedroom/ 2 bath eyebrow style home just two blocks off iconic Duval Street ...
From $258 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Colorful beachfront condo w\/ ocean view balcony & shared hot tub\/pool\/tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Atlantic Parrot Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $180 per night (USD)Expedia
- From $346 per night (USD)
VRBO
2bed 2bath condo w\/ lagoon pool, private balcony, parking, close to beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $346 per night (USD)VRBO
- From $177 per night (USD)
Expedia
Bright Keys Cottage with Enclosed Yard, Deck, Porch, Partial, AC, & WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Key Rest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $177 per night (USD)Expedia
- From $379 per night (USD)
VRBO
MONTHLY RENTAL, block to Duval, POOL, your own personal resort, 3 BR\/ 3 BA
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to "Shipwrecked in Paradise"! Historic Key West Eyebrow House with private pool..... ONE block to Duval, the He ...
From $379 per night (USD)VRBO
- From $1096 per night (USD)
VRBO
A KEY ESCAPE ~ 3 Bedroom, 2.5 Bathroom Home in Old Town w\/ Private Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
KEY WEST IN STYLE... Imagine carefree days in the tropics, spent in the comfort of this exceptionally located retreat wi ...
From $1096 per night (USD)VRBO
- From $620 per night (USD)
VRBO
Modern and spacious historic home with private pool and off-street parking.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Brisa Azul (Blue Breeze) is located in the heart of Old Town Key West and will provide the perfect venue to experience t ...
From $620 per night (USD)VRBO
- From $412 per night (USD)
VRBO
KATE'S KRAWL OFF DUVAL ~ 1 BR, 1 Ba Home w\/ Outdoor Area Steps to Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
SALT AIR & SUNSHINE... This 1 bedroom, 1 bathroom private home is a sweet surprise just off Duval St. It's a breath of f ...
From $412 per night (USD)VRBO
- From $1084 per night (USD)
VRBO
TROPICAL RETREAT ~ 3 Bedroom, 3.5 Bath 1\/2 Block From Duval St. w\/ Pool!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
SPOIL YOURSELF IN PARADISE... Indulge yourself in the rustic charm of historic Key West enveloped in lush, vibrant surro ...
From $1084 per night (USD)VRBO
- From $181 per night (USD)
VRBO
A “whole” in one vacation home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Amazing two bedroom townhouse with two decks, two bathrooms and a open kitchen in the famous Key West Golf Course resort ...
From $181 per night (USD)VRBO
- From $291 per night (USD)
VRBO
**CASITA OLIVIETTA @ SOLARES HILL** Brand New Home & Private Pool + LAST KEY SER
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! You don’t oft ...
From $291 per night (USD)VRBO
- From $220 per night (USD)
VRBO
INTO THE MYSTIC ~ Adorable 2 Bedroom, 3 Bathroom Townhome w\/ Community Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
YOUR PEACEFUL PARADISE AWAITS… Find this unmatched island escape tucked away in the lust and intimate Southernmost Caban ...
From $220 per night (USD)VRBO
- From $357 per night (USD)
VRBO
CROOKED PALM ~ 3 Bedroom, 3 Bathroom Luxury Home w\/ Pool & Compact Parking!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
LET THE REAL WORLD SLIP AWAY... Experience quintessential island serenity within this charming and newly renovated home ...
From $357 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin
- Bedrooms:
- 2
- 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 $250 per night (USD)Expedia
- From $1228 per night (USD)
VRBO
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w\/ Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BEGIN YOUR ISLAND ESCAPE... Come get lost in the magic of this captivating island retreat offering modern amenities with ...
From $1228 per night (USD)VRBO
- From $971 per night (USD)
VRBO
ISLAND OASIS ~ Stylish 2 Bedroom, 2 Bath Home w\/ Private Heated Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
YOUR SOUTHERN SANCTUARY... Find your serenity in this stylish and cheery townhome, just a short distance away from the s ...
From $971 per night (USD)VRBO
- From $391 per night (USD)
VRBO
Parrotville - 2 bedroom \/ 2 bath Townhome Close to Duval
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Parrotville is part of the Windward Park gated community just off Simonton Street, one block from Duval Street. A total ...
From $391 per night (USD)VRBO
- From $240 per night (USD)
Expedia
FORE REEL at the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Fore Reel! Have you ever dreamed of living in a quaint Key West Golfing gated community with so many wonderfu ...
From $240 per night (USD)Expedia
- From $250 per night (USD)
VRBO
ISLAND TIME at Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Island Time***PLEASE NOTE THIS IS A MONTHLY RENTAL ONLY***This is a beautiful, private two-story open plan townhome back ...
From $250 per night (USD)VRBO
- From $323 per night (USD)
Expedia
~LA MAISONNETTE~ Gated condominium 1 block from the allure of Duval Street.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Location, location, location, is what this chic condominium is all about! From here you can walk 1 block t ...
From $323 per night (USD)Expedia
- From $155 per night (USD)
VRBO
Escape the Snow - Paradise awaits. A month in Key West Jan 15th- Feb 18th 22
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located facing the tranquil lush courtyard at 1800 Atlantic. This spacious family retreat features a renovated kitchen. ...
From $155 per night (USD)VRBO
- From $499 per night (USD)
Expedia
**THE BEAMING BARRACUDA @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERV
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! THE BEAMING B ...
From $499 per night (USD)Expedia
- From $487 per night (USD)
VRBO
Hyatt Beach House! Quiet Key West Location! Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on a private beach, this quiet piece of Key West is an excellent choice for relaxation while also situated only ...
From $487 per night (USD)VRBO
- From $571 per night (USD)
Expedia
Sunset Harbor - Old Town Key West Location - Beautiful Property
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located ...
From $571 per night (USD)Expedia
- From $460 per night (USD)
VRBO
The Galleon Resort Best Resort Location in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
June unit 1bd 1ba with pull out sofa-sleeps 4, 5th floor with large balcony, great marina views. The Galleon Resort has ...
From $460 per night (USD)VRBO
- From $368 per night (USD)
VRBO
Zen Cigar Maker Cottage, magical serpentine pool, serene landscaping, pkg\/bikes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the Key West Shire! A sublime sanctuary where all your worldly troubles melt away and relaxation is paramoun ...
From $368 per night (USD)VRBO
- Click For Pricing
VRBO
Studio at Hyatt Residence Club Key West, Sunset Harbor.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Seth Nock Licensed Broker, Selling Timeshares INC. Studio at Hyatt Residence Club Key West, Sunset Harbor. Check-in: ...
Click For PricingVRBO
- From $250 per night (USD)
Expedia
Anchors Away - Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Anchors Away offers traditional Conch style living and is located in the coveted Old Town Key West. This home is unbeata ...
From $250 per night (USD)Expedia
- From $327 per night (USD)
VRBO
LATITUDE ADJUSTMENT ~ Prestigious 3 Bedroom, 3.5 Bathroom Home with Pool!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
UNMATCHED ISLAND RETREAT… Tucked away within one of the island’s most impressive lanes in the Casa Marina district, this ...
From $327 per night (USD)VRBO
- From $250 per night (USD)
Expedia
TAILGATE KEY at the Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Tailgate Key! This unique vacation property is located in the Key West Golf Club Community set amongst lush t ...
From $250 per night (USD)Expedia
- From $437 per night (USD)
VRBO
SWEET'S SPOT at The Truman Annex in Key West
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 6
This Harbour Place condominium is in Key West's most prestigious community of Truman Annex offering breathtaking water a ...
From $437 per night (USD)VRBO
- From $182 per night (USD)
VRBO
**LARGE PRIVATE HEATED POOL and PATIO**1\/3 Mile from Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Located on a quiet residential street in the beautiful key west neighborhood of casa marina just blocks from Higgs Beach ...
From $182 per night (USD)VRBO
- From $338 per night (USD)
VRBO
Red Room at Grand Maloney Hotel with Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $338 per night (USD)VRBO
- From $368 per night (USD)
Expedia
Road's End by Brightwild | Steps to Duval St!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Just a stone's throw away from Mile Marker Zero lies the aptly named "Road's End," a charming 1 Bd, 1.5 Bth tow ...
From $368 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Perfect 2 BR Escape Near Smathers Beach w Bikes, fishing poles & Beach Chairs!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sophisticated 2 bedroom, 1 bathroom Key West Home just steps from the white sand and salty hues of Smathers Beach, short ...
From $225 per night (USD)VRBO
- From $307 per night (USD)
Expedia
BEST TIME at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This Shipyard unit is a one level condominium on the second floor which has 2 decks to enjoy the beautiful weather and e ...
From $307 per night (USD)Expedia
- From $653 per night (USD)
VRBO
**ISLAND OPULENCE @ MIDTOWN** Grand Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 11
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The moment yo ...
From $653 per night (USD)VRBO
- From $283 per night (USD)
Expedia
African Queen by Brightwild | GREAT Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: African Queen Cottage is part of the quiet complex called "Harborwalk Hideaways," located in the Historic Seapo ...
From $283 per night (USD)Expedia
- From $321 per night (USD)
VRBO
Pilar's Cottage by Brightwild | Studio w\/Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Pilar Cottage is part of the quiet complex called "Harborwalk Hideaways," located in the Historic Seaport distr ...
From $321 per night (USD)VRBO
- From $1255 per night (USD)
Expedia
Harborwalk Hideaways by Brightwild |Prime Location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: Harborwalk Hideaways is a stunning, newly-renovated vacation rental complex tucked away in the Historic Seaport ...
From $1255 per night (USD)Expedia
- From $350 per night (USD)
VRBO
POOLSIDE HANGOVER at The Truman Annex in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is an amazing two bedroom TWO BATH condo over by the gorgeous pool. Fully equipped for you to enjoy your time away ...
From $350 per night (USD)VRBO
- From $775 per night (USD)
Expedia
Windsor Townhome #4- 3 bedroom 3.5 bath with private pool
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently ...
From $775 per night (USD)Expedia
- Click For Pricing
VRBO
PAGITT HOUSE: Old Town - Private Pool - 3BR/2BA - Sleeps 6 - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
WELCOME TO PAGITT HOUSE! Experience the original Key West by staying at this historical treasure! Pagitt House is a ...
Click For PricingVRBO
- From $1157 per night (USD)
Expedia
A Place on Emma at the Truman Annex in Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Beautifully renovated & furnished 4 bedroom/ 4 bath single family home including a charming detached guest cottage is lo ...
From $1157 per night (USD)Expedia
- From $260 per night (USD)
VRBO
A DUCK ON THE GREEN at the Key West Golf Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
A Duck on the Green --This lovely, fully furnished, townhouse has two and a half bedrooms that sleeps up to five and two ...
From $260 per night (USD)VRBO
- From $307 per night (USD)
Expedia
SOUTHERNMOST SANCTUARY at The Truman Annex in Key West
- 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 $307 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Incredible 2BR Penthouse condo on Front Street with amazing amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is one of Key West's best resorts. Located on Front Street in front of the Marina, it has a large wat ...
From $500 per night (USD)VRBO
- From $302 per night (USD)
VRBO
QUEEN OF SOL ~ 3 Bed, 2 Bath in Peaceful Neighborhood with Dip Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
YOUR PIECE OF PARADISE… Residing in an attractive neighborhood at the highest point of Key West referred to as “Solares ...
From $302 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Come escape to Island Time Hideaway - Wonderful monthly renovated rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully renovated 2 bedroom 2 bath condo at the exclusive 1800 Atlantic Condo's. Each bedroom has a king size bed an ...
From $150 per night (USD)VRBO
- From $479 per night (USD)
VRBO
SAILOR HOUSE ~ Charming 2 Bedroom, 1.5 Bathroom Just Steps to Duval St!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FAR FROM ORDINARY... Extraordinary moments and blissful surroundings lie ahead for your Key West adventure as you soak i ...
From $479 per night (USD)VRBO
- From $184 per night (USD)
VRBO
Beautiful Marina location. Gated community. Quite and secure. SUNSETS !!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunset Marina Condominium Complex is a gated community that has a community pool and spa, and clubhouse. All of the two ...
From $184 per night (USD)VRBO
- From $570 per night (USD)
VRBO
PARADISE PLACE:A tastefully decorated space in the heart of Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Open the door to Paradise Place and find yourself transported to a peaceful sanctuary. The downstairs living area is ...
From $570 per night (USD)VRBO
- From $584 per night (USD)
VRBO
VILLA SERENA@DUVAL SQUARE - A peaceful retreat in the heart of Old Town.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Villa Serena is the perfect space ...
From $584 per night (USD)VRBO
- From $230 per night (USD)
Expedia
Margaritaville: Live Like a Local in Old Town Key West! Dog-Friendly Conch House with Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "Margaretaville," your quintessential Key West getaway that offers you the chance to experience life as a loc ...
From $230 per night (USD)Expedia
- From $374 per night (USD)
VRBO
2Bed 2Bath Shipyard in Truman Annex w\/ shared pool, close to Duval, parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $374 per night (USD)VRBO
- From $1563 per night (USD)
Expedia
Captain's Daughter: Oversized home for the whole family w\/private pool & 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 $1563 per night (USD)Expedia
- From $364 per night (USD)
VRBO
HIGH TIDE at The Truman Annex in Key West
- 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 restaura ...
From $364 per night (USD)VRBO
- From $255 per night (USD)
Expedia
SHELLABRATION at the Key West Golf Club
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY***** This prime two bedroom, two and a half bath fully furnished ...
From $255 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Old Town 4 \/4.5 house with private pool and 2 poolside cottages + outdoor shower
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Newly restored Key West property in old town. Blocks from Duval and the harbor. Private heated pool central AC washer dr ...
From $500 per night (USD)VRBO
- From $340 per night (USD)
VRBO
Beautifully remodeled 1920's home located in old town close to everything.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Location, location, location. A perfect retreat to relax and recharge, or the perfect starting point to explore all tha ...
From $340 per night (USD)VRBO
- From $350 per night (USD)
VRBO
A CONCH ESCAPE at The Truman Annex in Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Location, location, adorable two bedroom, one bath second floor condo overlooking the Truman Waterfront Park is the per ...
From $350 per night (USD)VRBO
- From $336 per night (USD)
Expedia
A SUNSET VIEW at The Truman Annex in Key West
- 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 $336 per night (USD)Expedia