Key West National Wildlife Refuge Rentals
- From $275 per night (USD)
VRBO
Heart of Old Town; 2 Bicycles, Grill, High Speed WiFi, 1st Floor, Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Our condo has always ...
From $275 per night (USD)VRBO
- From $1095 per night (USD)
VRBO
Rare Penthouse 2 bed\/2bath additional King in loft
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath ...
From $1095 per night (USD)VRBO
- From $723 per night (USD)
VRBO
The Galleon Resort in Beautiful Key West. Amazing Views! Over 500 Reviews!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
These are 7-night rentals, with check-in on Saturdays only. Overlooking the shimmering span of Gulf of Mexico in histor ...
From $723 per night (USD)VRBO
- From $589 per night (USD)
VRBO
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 $589 per night (USD)VRBO
- From $308 per night (USD)
VRBO
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 $308 per night (USD)VRBO
- From $795 per night (USD)
Expedia
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 $795 per night (USD)Expedia
- From $100 per night (USD)
VRBO
Private Home in Heart of Old Town (Shared Pool!)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Come escape to paradise in this newly updated and available home steps from Duval! Equipped with all the amenities for a ...
From $100 per night (USD)VRBO
- From $310 per night (USD)
Expedia
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 $310 per night (USD)Expedia
- From $433 per night (USD)
VRBO
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR\/2BA Condo & Pool + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OLD TOWN OASI ...
From $433 per night (USD)VRBO
- From $1500 per night (USD)
VRBO
Key West Suites Hotel - Adam Scott Rote Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central ...
From $1500 per night (USD)VRBO
- From $345 per night (USD)
VRBO
Key West Rooster
- 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 $345 per night (USD)VRBO
- From $287 per night (USD)
Expedia
The Maria Luz, a Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Maria Luz a is located in a Historic Conch house from the early 1900’s updated and decorated by its owner. Feature ...
From $287 per night (USD)Expedia
- From $234 per night (USD)
VRBO
The Gisela, a Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
The Gisela is located in the rear of an adorable Conch Cottage. Finished with a soft and neutral color scheme that will ...
From $234 per night (USD)VRBO
- From $855 per night (USD)
VRBO
SEAPORT SKYLINE at Galleon Resort near Mallory Square—King Suite-Beach-Pool-BBQ
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
OCEANFRONT CASUAL LUXURY CONDO RENTAL WITH BREATHTAKING VIEWS OF KEY WEST HARBOR AND THE GULF OF MEXICO. PENTHOUSE COND ...
From $855 per night (USD)VRBO
- From $294 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $294 per night (USD)VRBO
- From $401 per night (USD)
Expedia
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $401 per night (USD)Expedia
- From $400 per night (USD)
VRBO
A Touch of Bermuda at Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping ...
From $400 per night (USD)VRBO
- From $220 per night (USD)
Expedia
Caroline On My Mind-New Listing-Light, Bright and Airy!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting exp ...
From $220 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Villa Nomade at Shipyard Condominiums
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped kitchen with bar seating and dining area. Th ...
From $313 per night (USD)VRBO
- From $635 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Minimum Age: 25 years old Pet Policy: No Pets An ID and credit card for a refundable security deposit will be required. ...
From $635 per night (USD)VRBO
- From $352 per night (USD)
VRBO
Rose Lane Villas - Villa Porta - 1 Bedroom - 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 with ...
From $352 per night (USD)VRBO
- From $675 per night (USD)
Expedia
Beach Paradise in the Keys! Location! Location! 2 Blocks to Duval St
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
You will love our newly renovated 2 bed/ 2 1/2 bath private townhome in a secure community. Perfect location. This prope ...
From $675 per night (USD)Expedia
- From $345 per night (USD)
VRBO
Perfect Location to Key West Action! Garden View, Pool, Bike Rental!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $345 per night (USD)VRBO
- From $415 per night (USD)
VRBO
Wonderful Stay, Amazing Location! 3 Pools, Bar, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $415 per night (USD)VRBO
- From $487 per night (USD)
VRBO
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! While Old Tow ...
From $487 per night (USD)VRBO
- From $401 per night (USD)
VRBO
Amazing Stay, Great Location! Bike Rental, Pools, Onsite Bar
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $401 per night (USD)VRBO
- From $359 per night (USD)
VRBO
Luxurious Vacation! Pools, Tiki Bar, Bike Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $359 per night (USD)VRBO
- From $752 per night (USD)
Expedia
Sunset Harbor - Old Town Key West Location - Beautiful Property
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the perfect location in old town Key West. Situated on the western side of the island, this resort is located ...
From $752 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Treasure Cove- 2BDR\/2.5BA | 2 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
~~7 day minimum~~Experience the famous island city of Key West and stay at the Treasure Cove Townhouse in the private P ...
From $350 per night (USD)VRBO
- From $300 per night (USD)
VRBO
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 ...
From $300 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Rarely Available! Quiet Lane in the Heart of Old Town, Sleeps 4 + 🐶🐾
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unbeatable location just 1 block from the iconic Green Parrot Bar and 2 blocks from world famous Duval Street. Blue Heav ...
From $150 per night (USD)VRBO
- From $224 per night (USD)
Expedia
Tropical Jewel: Historic Seaport Oldtown - 2BR\/2BA - Pool - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WELCOME TO TROPICAL JEWEL! Near all the action of the historic seaport and Duval Street, you can get out into the cit ...
From $224 per night (USD)Expedia
- From $375 per night (USD)
VRBO
A Touch Of Cuba In Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Conch Republic and the Shipyard section of the Truman Annex. You have many choices of accommodations and sin ...
From $375 per night (USD)VRBO
- From $275 per night (USD)
Expedia
MAI TAI TERRACE - KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Mai Tai Terrace located in The Shipyard subdivision of Truman Annex in beautiful Key West. This 2-bedroom, ...
From $275 per night (USD)Expedia
- From $171 per night (USD)
VRBO
Conch Haven luxury 1 Bedroom Old Town MONTHLY
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short w ...
From $171 per night (USD)VRBO
- From $375 per night (USD)
Expedia
MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Featured in The Key West Citizen Home of the Week. Perfect location, and newly renovated with fresh paint, new kitchen w ...
From $375 per night (USD)Expedia
- From $394 per night (USD)
VRBO
Rose Lane Villas - Villa Rosa - 1 Bedroom - 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 $394 per night (USD)VRBO
- From $811 per night (USD)
Expedia
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & 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! Hidden amongs ...
From $811 per night (USD)Expedia
- From $285 per night (USD)
VRBO
Key West, Gated Truman Annex Condo, new Waterfront Park, and Ft. Zach Beach.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This condo has a unique location in the Gated Truman Annex. It is very quiet, but yet very close to all Key West has t ...
From $285 per night (USD)VRBO
- From $500 per night (USD)
VRBO
Truman Annex Best Location in Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
We stick to a Saturday check in during the in season months (Jan-April) Greetings from Paradise, where the temperature ...
From $500 per night (USD)VRBO
- From $285 per night (USD)
VRBO
Tropical Getaway! 3 Pools, Bike Rental, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $285 per night (USD)VRBO
- From $321 per night (USD)
VRBO
Wonderful Beach Vacation! 3 Pools, Tiki Bar, Bike Rentals, Pets Allowed, Dining!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $321 per night (USD)VRBO
- Click For Pricing
VRBO
Amazing Vacation! 4 Spacious Units! 3 Pools, Tiki Bar, Bike Rental!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
Click For PricingVRBO
- From $364 per night (USD)
VRBO
Family and Friends Vacation! Pet-friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tropical island paradise! Breathe in the ocean air from your private balcony. Step out on to legendary Duval Street, the ...
From $364 per night (USD)VRBO
- From $464 per night (USD)
VRBO
ADMIRAL'S PARADISE in Key West
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ...
From $464 per night (USD)VRBO
- From $975 per night (USD)
Expedia
Sky Suites Retreat by Brightwild–2 Stunning Condos
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: This elegant, elevated 2nd story loft with vaulted ceilings has been designed for your next dream Key West geta ...
From $975 per night (USD)Expedia
- From $158 per night (USD)
VRBO
Old Town Beauty built in 1883
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 ...
From $158 per night (USD)VRBO
- From $504 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Minimum Age: 25 years old Pet Policy: No Pets An ID and credit card for a refundable security deposit will be required. ...
From $504 per night (USD)VRBO
- Click For Pricing
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Minimum Age: 25 years old Pet Policy: No Pets An ID and credit card for a refundable security deposit will be required. ...
Click For PricingVRBO
- From $390 per night (USD)
VRBO
Miami Vice Sailboat Key West North Fleming Key
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Our business is growing with new natural setting stay at our moorings in quiet secluded area in Key West Harbor!” We h ...
From $390 per night (USD)VRBO
- From $149 per night (USD)
VRBO
ISLAND PEARL - Cozy Nightly Rental just off Duval RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
WELCOME TO ISLAND PEARL Nestled in the heart of Key West, located behind a main house, the Island Pearl vacation rent ...
From $149 per night (USD)VRBO
- From $250 per night (USD)
Expedia
SUMMER LOVIN~Incredibly Located 3 Bedroom, 3 Bathroom Home w\/ Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
SIMPLY CHARMING... An ideal way to spend your tropical vacation immersed in this historic, charming abode showcasing mod ...
From $250 per night (USD)Expedia
- From $292 per night (USD)
VRBO
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! It is not so ...
From $292 per night (USD)VRBO
- From $1029 per night (USD)
VRBO
Waterfront Views from Dolphin Watch
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Dolphin Watch is located in prestigious Truman Annex and is one of the few private waterfront homes. We are less than tw ...
From $1029 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Location, Location, Location!!! Downtown Key West - Truman Annex!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
All the amenities of a fantastic resort suite and free assigned parking in the middle of everything in Key West...2/1 th ...
From $300 per night (USD)VRBO
- Click For Pricing
Expedia
Sunset views at the Galleon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You will be back year after year! Unit features full kitchen with Master King, Guest Twin Beds, and Pull out Sleeper Sof ...
Click For PricingExpedia
- Click For Pricing
Expedia
Pilar`s Secret - An oasis right off Duval Street - Sleeps up to 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Pilar’s Secret is tucked away in the heart of Key West just half a block off famous Duval Street. This hidden oasis is t ...
Click For PricingExpedia
- From $595 per night (USD)
Expedia
Downtown Retreat - A++ Location W\/ Private Heated Pool\/Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in ...
From $595 per night (USD)Expedia
- From $488 per night (USD)
VRBO
Galleon Resort Efficiency Historic District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
$25,00 Renovation completed end of 2016/beginning of 2017!! Different than ANY other Efficiency at the Galleon!! You w ...
From $488 per night (USD)VRBO
- From $752 per night (USD)
VRBO
Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
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 $752 per night (USD)VRBO
- From $315 per night (USD)
VRBO
Shabby Chicken Truman Annex: Sunny, Oversized 2BR KING\/twin, 1Bath,1st Flr, Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Amazing LOCATION! Truman Annex: SHABBY CHICKEN - come stay at the large & proud bird in town!! Large front yard and po ...
From $315 per night (USD)VRBO
- From $1165 per night (USD)
VRBO
Palm Trees Ocean Breeze Key West FL
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Three bedroom, four bathroom private home with heated pool . Breathtaking sunsets can be seen from third floor deck over ...
From $1165 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Truman Annex - Beautiful Townhome - President's Lane
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2-story townhouse; master bedroom with King Bed and double doors to deck; full bath; second bedroom with two t ...
From $300 per night (USD)VRBO
- From $370 per night (USD)
VRBO
A Truman Annex Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our lovely condo which is located in the famed Truman Annex Complex right in the heart of fabulous Key West. ...
From $370 per night (USD)VRBO
- From $700 per night (USD)
VRBO
WASTIN AWAY IN MARGARITAVILLE! HYATT RESIDENCE CLUB JEWEL IN HEART OF KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
ONLY AVAILABLE 2/20-2/27: PRIME REAL ESTATE IN THE HEART OF KEY WEST. HYATT RESIDENCE CLUB COVETED RESORT SUNSET HARBOR ...
From $700 per night (USD)VRBO
- From $626 per night (USD)
Expedia
~Serene Lily~ Luxurious 2 bed, 2.5 bath home in the upscale Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
WEEKLY RENTAL: This property has a 7 night minimum stay. THE PROPERTY: Located where the Gulf meets the Atlantic, this ...
From $626 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Beautiful sunsets!! Harbour Place, Truman Annex. Walk or bike to everything!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Harbor Place is one of the most prestigious properties in Key West! This unit offers breath taking water views overlook ...
From $450 per night (USD)VRBO
- From $457 per night (USD)
Expedia
NEW YEAR - NEW CRAZY LOW DEALS ON FANTASTIC HOME
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
City of Key West Business License # 28224 We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memo ...
From $457 per night (USD)Expedia
- From $786 per night (USD)
VRBO
Old Town Key West - Historic & Charming - 2 Blks From Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
OVERVIEW The Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described as ...
From $786 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Key West Hen
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Give me a call if you have any questions! 702-232-3750 Welcome to your home away from home and enter through the canop ...
From $299 per night (USD)VRBO
- From $753 per night (USD)
VRBO
Tropical State of Mind Key West FL
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 5
Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition TV found in every bedroom in ...
From $753 per night (USD)VRBO
- From $444 per night (USD)
VRBO
Key West 44ft Sailboat Wild Thing - spring and summer openings now.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
*Our business model has changed. We no longer are located at a dock; We are excited to share our moorings at North Flem ...
From $444 per night (USD)VRBO
- From $375 per night (USD)
VRBO
**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! COLORS OF THE ...
From $375 per night (USD)VRBO
- From $458 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Fleming House 2 bdrm 2.5 bath private house
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
We are Craig & Cindy and we thank you for inquiring about our Truman Annex Key West vacation homes. Truman Annex is ide ...
From $458 per night (USD)Expedia
- From $850 per night (USD)
VRBO
Namaste 'The Spirit Within Me Salutes The Spirit Within You'
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom B ...
From $850 per night (USD)VRBO
- From $851 per night (USD)
VRBO
Heavenly Hideout at Rainbow's End
- 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 $851 per night (USD)VRBO
- From $400 per night (USD)
VRBO
Old Town Bali Hideaway For 2, Just Steps From Duval
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound j ...
From $400 per night (USD)VRBO
- From $379 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 $379 per night (USD)VRBO
- From $666 per night (USD)
VRBO
Hyatt Sunset Harbour Resort-Prime location on Key West!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
All rentals will be in seven-night increments with a Friday through Sunday for check-in. Thank you for choosing Dash R ...
From $666 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Cozy Piece of Key West History
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PERFECTLY located, 100 y-o "Conch" House, w AAA+ front-porch, and 3 full baths to go w 3 BRs... brand-new kitchen, compl ...
From $300 per night (USD)VRBO
- From $208 per night (USD)
VRBO
THE OLD SAPODILLA HOUSE ~ Pet Friendly Home in Historic Bahama Village
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PERFECT GETAWAY JUST STEPS FROM DUVAL... Private family home with poolside cottage totals three bedrooms and three full ...
From $208 per night (USD)VRBO
- From $177 per night (USD)
VRBO
~ THE PINK HOUSE ~ Saline pool, lush privacy and 2 ensuites with balconies.
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 5
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $177 per night (USD)VRBO
- From $366 per night (USD)
VRBO
~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
WEEKLY RENTAL: This property has a 7 night minimum stay. THE PROPERTY: As you open the white picket gate to this thre ...
From $366 per night (USD)VRBO
- From $1191 per night (USD)
VRBO
~ CLOUD 9 ~ It's heaven on earth in this 3B\/3BA lavish home with pool\/parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
THE PROPERTY: If you are looking for a peaceful retreat that is close to everything, this is the ultimate home for you. ...
From $1191 per night (USD)VRBO
- From $269 per night (USD)
VRBO
~ SEAS THE DAY ~ Nestled in a gated community by Fort Zachary Taylor beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
**Home is available September 1 for a monthly rental (only). 28 night minimum** WEEKLY RENTAL: This property has a 7 n ...
From $269 per night (USD)VRBO
- Click For Pricing
VRBO
Very Rare-The Galleon 3 King Bd, 3 Bath w\/ 4th king bd in loft + sleeper sofa
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
The Galleon Resort in Key West is a Perfect Resort for you, your Guests and your Family. The unit is spacious and very b ...
Click For PricingVRBO
- From $941 per night (USD)
VRBO
**BRISA FRESCA @ THE ANNEX** Airy Home by Duval & Beach + 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! A trip to Key ...
From $941 per night (USD)VRBO
- From $365 per night (USD)
Expedia
**VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + 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! VILLA BAHAMA ...
From $365 per night (USD)Expedia
- From $2130 per night (USD)
VRBO
**THE ROYAL COMPOUND @ THE ANNEX** Lush Estate & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in th ...
From $2130 per night (USD)VRBO
- From $995 per night (USD)
Expedia
**BAHAMIAN BAMBOO @ THE ANNEX** Chic Home By Duval & Beach + LAST KEY SERVICES.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! BAHAMIAN BAMB ...
From $995 per night (USD)Expedia
- From $589 per night (USD)
VRBO
**GULFSIDE VISTAS @ THE ANNEX** Ocean Penthouse & Pool + LAST KEY SERVICE...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! GULFSIDE VIST ...
From $589 per night (USD)VRBO
- From $1200 per night (USD)
Expedia
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a truly o ...
From $1200 per night (USD)Expedia
- From $349 per night (USD)
VRBO
**SALTWATER HARMONY @ THE ANNEX** Charming Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SALTWATER HAR ...
From $349 per night (USD)VRBO
- From $355 per night (USD)
Expedia
**LA PETITE PENTHOUSE @ THE ANNEX** Elegant Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! LA PETITE PEN ...
From $355 per night (USD)Expedia
- From $1350 per night (USD)
VRBO
**CONCH CASA GRANDE @ THE ANNEX** Home+ Pool near Duval + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CONCH CASA GR ...
From $1350 per night (USD)VRBO
- From $344 per night (USD)
Expedia
**LA GRANDE REUNION @ OLD TOWN** Estate & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling wit ...
From $344 per night (USD)Expedia
- From $486 per night (USD)
VRBO
**PROMENADE TO PARADISE @ THE ANNEX** Ocean Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! If you dream ...
From $486 per night (USD)VRBO
- From $470 per night (USD)
Expedia
**BLUE HERON'S COVE @ THE ANNEX** Luxury Villa by Duval + 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! BLUE HERON'S ...
From $470 per night (USD)Expedia
- From $815 per night (USD)
VRBO
**SEA CAPTAIN'S HAVEN @ THE ANNEX** Luxury Villa & 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! SEA CAPTAIN'S ...
From $815 per night (USD)VRBO
- From $434 per night (USD)
Expedia
**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + 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! This Old Town ...
From $434 per night (USD)Expedia