Fleming Key Rentals
From $1238 per night (USD)VRBO
Rare Penthouse 2 bed\/2bath additional King in loft
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath ...
From $1238 per night (USD)VRBO
From $913 per night (USD)Expedia
The Galleon Resort in Beautiful Key West. Amazing Views! 2 bedroom villa!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Concierge Realty is proud to present luxury villas at The Galleon Resort! **Reservations are available in weekly (7 nig ...
From $913 per night (USD)Expedia
From $611 per night (USD)VRBO
BOTTOMS UP BUNGALOW - 2 Bedroom \/ 2 Bathroom With PRIVATE POOL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West. This pristine Florida Bungalow ...
From $611 per night (USD)VRBO
From $765 per night (USD)Expedia
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 $765 per night (USD)Expedia
From $1529 per night (USD)VRBO
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 $1529 per night (USD)VRBO
From $299 per night (USD)Expedia
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 $299 per night (USD)Expedia
From $662 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 $662 per night (USD)VRBO
From $2186 per night (USD)Expedia
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 $2186 per night (USD)Expedia
From $277 per night (USD)VRBO
The Rex, a Key West Monthly Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located apartment. Just a short walk from some of Key West best restaurants ...
From $277 per night (USD)VRBO
From $337 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 $337 per night (USD)Expedia
From $276 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 $276 per night (USD)VRBO
From $872 per night (USD)Expedia
SEAPORT SKYLINE at Galleon Resort-Beach-Pool-King Suite-BBQ-Rooftop views!
- 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 $872 per night (USD)Expedia
From $370 per night (USD)VRBO
The Caribbean Suite - 2-K-bedroom \/1 bath\/ kitchenette\/sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
This deluxe "Key West Charmer" is a beautifully restored Victorian home built in the 1880's that was converted into indi ...
From $370 per night (USD)VRBO
Click For PricingExpedia
Cozy studio cottage in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to ...
Click For PricingExpedia
From $233 per night (USD)VRBO
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 $233 per night (USD)VRBO
From $662 per night (USD)Expedia
Heart of Key West - 2BR Waterfront at the Galleon Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $662 per night (USD)Expedia
From $506 per night (USD)VRBO
Rose Lane Villas - Villa Porta - 1 Bedroom - Downtown Key West
- Bedrooms:
- 1
- 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 $506 per night (USD)VRBO
From $360 per night (USD)Expedia
Welcome to the Shady Palms - Private Pool - RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $360 per night (USD)Expedia
From $376 per night (USD)VRBO
TRANQUILITY - Meadows Monthly Rental - Private Pool - 3BDR\/3BA - RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Tranquility, a luxurious vacation rental nestled in a tropical setting. This stunning 3 bedroom, 3 bathroom h ...
From $376 per night (USD)VRBO
From $501 per night (USD)Expedia
CONCH COTTAGE: Old Town - Hot Tub - 1 Block from Duval - 1BD\/1BA RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
WELCOME TO CONCH COTTAGE! In the 20th century many residents of Key West began referring to themselves as “Conchs”, no ...
From $501 per night (USD)Expedia
From $792 per night (USD)VRBO
ISLAND TIME - 5 Bed\/3 Bath OldTown Complex - MONTHLY - Private pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
WELCOME TO ISLAND TIME! Key West Island Time is a rare find in old town Key West. It is a total of 5 bedrooms and three ...
From $792 per night (USD)VRBO
From $261 per night (USD)Expedia
Heavenly Hideaway-Monthly 3BD 2.5BA Private Pool - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
HEAVENLY HIDEAWAY! Welcome to our Heavenly Hideaway, a serene oasis nestled in the heart of Key West. This enchanting 3 ...
From $261 per night (USD)Expedia
From $348 per night (USD)VRBO
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $348 per night (USD)VRBO
From $273 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 $273 per night (USD)Expedia
From $546 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 $546 per night (USD)VRBO
From $811 per night (USD)Expedia
Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Down a hidden lane in the heart of Old Town Key West you will find Loco Court. The compound is located one block off Duv ...
From $811 per night (USD)Expedia
From $1025 per night (USD)VRBO
Getaway in Key West: Tranquil Room w\/ Balcony | Resort w\/ Pool Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1025 per night (USD)VRBO
From $964 per night (USD)VRBO
Old Town Key West Family Retreat | Spacious Room w\/ Balcony | Parking Onsite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $964 per night (USD)VRBO
From $454 per night (USD)VRBO
THE FICUS HOUSE ~ Adult Only, Lush 3 BR, 2.5 Ba Gem with Pool and Cottage!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
VINTAGE ISLAND PARADISE... Tucked within luxuriant foliage lies this timeless, adult only, tropical sanctuary in the mid ...
From $454 per night (USD)VRBO
From $920 per night (USD)VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $920 per night (USD)VRBO
From $531 per night (USD)VRBO
PURA VIDA ~ 3 Bed\/3.5 Bath Home on Quaint Old Town Lane!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $531 per night (USD)VRBO
From $565 per night (USD)Expedia
Miami Vice Sailboat Used For TV Series Ready To Charter! Includes 2 Hour Sail
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Our business is now in a pristine marina at the stock island division in Key West. Perry Marina has a shuttle that ru ...
From $565 per night (USD)Expedia
From $475 per night (USD)VRBO
Casa Verde - Perfection in a monthly rental - private pool - RealKeyWest
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
As you step through the door, you are enveloped in a serene atmosphere highlighted by soothing tropical colors and impre ...
From $475 per night (USD)VRBO
From $409 per night (USD)Expedia
**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 60 days prior to your arrival! It is not so ...
From $409 per night (USD)Expedia
From $450 per night (USD)VRBO
**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If you’re loo ...
From $450 per night (USD)VRBO
From $265 per night (USD)Expedia
Runaway Bills | 3 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
This stylish Conch Home is tucked away on a quiet lane in Old Town Key West. Surrounded by distinctive neighborhoods thi ...
From $265 per night (USD)Expedia
From $492 per night (USD)VRBO
Sunset South: First Floor 2 Bedroom 1 Bath Condo at Bayfront Suites & Marina
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $492 per night (USD)VRBO
From $433 per night (USD)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 ...
From $433 per night (USD)Expedia
From $991 per night (USD)VRBO
Upper Bayview North: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $991 per night (USD)VRBO
From $609 per night (USD)Expedia
Town Home with King Bed, Full Kitchen, and Pullout Sofa
- Bedrooms:
- 0
- Bathrooms:
- 0
- Sleeps:
- 4
This is a two-story Victorian Town Home with 1st and 2nd floor private verandas overlooking historic Fleming Street. It ...
From $609 per night (USD)Expedia
From $1070 per night (USD)VRBO
Downtown Retreat - A++ Location W\/ Private Heated Pool\/Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in ...
From $1070 per night (USD)VRBO
From $208 per night (USD)Expedia
Just Restored One Bedroom Hideaway with Garden and Hot Tub 5 No Need For A Car
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This one bedroom apartment on the ground floor is completely restored with a full kitchen and laundry. This unit has eve ...
From $208 per night (USD)Expedia
From $319 per night (USD)VRBO
~ VILLA AZUL ~ Enjoy this historic home with pool house and parking.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $319 per night (USD)VRBO
From $488 per night (USD)Expedia
~ROOSTER CONCH~ Amazing location with shared pool and covered balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Enjoy your stay in the tropics at Rooster Conch, part of the highly touted "Queen Conch" complex, which in ...
From $488 per night (USD)Expedia
From $934 per night (USD)VRBO
SEA CONCH~ Amazing location with shared pool, deck, and parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
THE PROPERTY: Enjoy your stay in the tropics at Sea Conch, part of the highly touted "Queen Conch" complex, which includ ...
From $934 per night (USD)VRBO
From $504 per night (USD)Expedia
~HORSE CONCH~ Amazing location with shared pool and covered balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Enjoy your stay in the tropics at Horse Conch, part of the highly touted "Queen Conch" complex, which incl ...
From $504 per night (USD)Expedia
From $2002 per night (USD)VRBO
~QUEEN CONCH ~ Amazing location with pool and room for family and friends!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
THE PROPERTY: Enjoy your stay in the tropics at the highly touted "Queen Conch" complex, which includes 3 separate renta ...
From $2002 per night (USD)VRBO
From $1030 per night (USD)Expedia
Upper Bayview South: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1030 per night (USD)Expedia
From $506 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 $506 per night (USD)VRBO
From $1080 per night (USD)Expedia
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 $1080 per night (USD)Expedia
From $802 per night (USD)VRBO
Historic \"Old Town\" Charm
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
* We are activally cleaning and sanitizing this rental with extra sanitation methods with each stay. LUXURY IN OLD TOWN ...
From $802 per night (USD)VRBO
From $875 per night (USD)Expedia
Middle Sunset: 3 Bedroom 3 Bath Luxury Condo at Bayfront Suites & Marina
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $875 per night (USD)Expedia
From $1047 per night (USD)VRBO
Bayview North One: Waterfront 4 Bedroom 4 Bath Condo at Bayfront Suites
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1047 per night (USD)VRBO
From $977 per night (USD)Expedia
Sunset North: Luxury 4 Bedroom 4.5 Bath Condo at Bayfront Suites & Marina
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $977 per night (USD)Expedia
From $881 per night (USD)VRBO
Upper Sunset South: Luxury 3 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $881 per night (USD)VRBO
From $955 per night (USD)Expedia
Bayview South: 4 Bedroom 3 Bath Waterfront Condo at Bayfront Suites & Marina
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $955 per night (USD)Expedia
From $983 per night (USD)VRBO
Upper Sunset North: Luxury 4 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $983 per night (USD)VRBO
From $923 per night (USD)Expedia
Bayview Middle: Waterfront 3 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $923 per night (USD)Expedia
From $187 per night (USD)VRBO
coral stone
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our apartment offers all the comforts of home, 120 paces to Duval Street - shopping, restaurants and nightlife. Near Hem ...
From $187 per night (USD)VRBO
From $328 per night (USD)Expedia
Hidden Treasure in Old Town: 3BR Home with Pool in Peaceful Gated Enclave
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 5
Your Key West Hideaway home is located in the heart of Old Town. Key West landmarks, attractions, Duval St, restaurants, ...
From $328 per night (USD)Expedia
From $210 per night (USD)VRBO
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
This 3 bedroom home is located one block from where Tennessee Williams home was located. The home has a true historic fl ...
From $210 per night (USD)VRBO
From $151 per night (USD)Expedia
Petite Pearl! Spacious 1 Bedroom, 1 Bath Pool Condo- RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Petite Pearl, your hidden gem nestled in the heart of the coveted Meadows district in Key West. A stone's thr ...
From $151 per night (USD)Expedia
From $509 per night (USD)VRBO
Key West 44ft Sailboat Wild Thing- stay 5 or more nights 1 night free!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Boats are located at the Perry Marina! Summer special starting 5/1/25 to 10/1/25 stay at docks we give you 5th free! We ...
From $509 per night (USD)VRBO
From $332 per night (USD)Expedia
Seaport Walkabout- the best location in town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Open to annual rental at lower rate Two hundred yards from Schooner Wharf and the seaport and steps from Pepe’s in the ...
From $332 per night (USD)Expedia
From $487 per night (USD)VRBO
LOVE LANDING ~ Charming 3 Bedroom, 3 Bathroom Home w\/ Pool and Parking!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
MARITIME-INSPIRED LIVING… Come unwind in this desirable retreat, tucked in a quiet and private lane just a stone's throw ...
From $487 per night (USD)VRBO
From $308 per night (USD)Expedia
The Hollinsed House \"Victorian Delights\" - Large 1 Bedroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $308 per night (USD)Expedia
From $817 per night (USD)VRBO
~ CASABLANCA GRANDE ~ Old Town quiet duplex with pool, hot tub, and parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
THE PROPERTY: Enjoy fresh air and sunshine from your front porch, private pool or hot tub at Casablanca Grande. You are ...
From $817 per night (USD)VRBO
From $732 per night (USD)Expedia
~ POINCIANA PARADISE ~ Casual duplex 2 blocks from Duval Street!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished duplex home comes with Key West charm and c ...
From $732 per night (USD)Expedia
From $293 per night (USD)VRBO
Hollinsed House Poolside \/ King Studio \/ sleeps 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $293 per night (USD)VRBO
From $636 per night (USD)Expedia
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 $636 per night (USD)Expedia
From $1059 per night (USD)VRBO
Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool
- 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 $1059 per night (USD)VRBO
From $433 per night (USD)Expedia
Old Town Bali Hideaway For 2, Just Steps From Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound j ...
From $433 per night (USD)Expedia
From $328 per night (USD)VRBO
ORCHID ESCAPE~ 2 bedroom 2 bath set in Old Town with private dip pool!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
CLASSIC OLD KEY WEST HOME... This home is boasting a rare combination of location and character. A mix of historic detai ...
From $328 per night (USD)VRBO
From $552 per night (USD)Expedia
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 $552 per night (USD)Expedia
From $687 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 $687 per night (USD)VRBO
From $388 per night (USD)Expedia
WANDERLUST ~ Stunning 3 Bed, 3 Bath Retreat in Peaceful Neighborhood w\/ Pool!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
STUNNING KEY WEST RETREAT… Just renovated, this island gem exudes the utmost island spirit with authentic historic chara ...
From $388 per night (USD)Expedia
From $1228 per night (USD)VRBO
~CHAVEZ HOUSE~ The private pool and lanai are a Key West dream come true!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
** Chavez House is available for 28 night minimum for the month of August ONLY. Live like a local! THE PROPERTY: By br ...
From $1228 per night (USD)VRBO
From $423 per night (USD)Expedia
~ SOLARIS COTTAGE ~ Live like a local in this bright and cozy retreat.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
THE PROPERTY: This one bedroom, one bath, first-floor duplex is conveniently located in Old Town. Walkable to so many Ke ...
From $423 per night (USD)Expedia
From $1296 per night (USD)VRBO
~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
THE PROPERTY: Nancy & Carl invite you to share their love of the island in their enchanted 3-bedroom home. Live like a l ...
From $1296 per night (USD)VRBO
From $480 per night (USD)Expedia
~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
THE PROPERTY: Enjoy fresh air and sunshine from your front porch or backyard hot tub at Casablanca Too. This unpretentio ...
From $480 per night (USD)Expedia
From $430 per night (USD)VRBO
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished first-floor duplex home comes with Key West ...
From $430 per night (USD)VRBO
From $505 per night (USD)Expedia
~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $505 per night (USD)Expedia
From $466 per night (USD)VRBO
~ SOLARIS GARDEN ~ Relax and enjoy this Bohemian dream on a quaint lane.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
THE PROPERTY: Bohemian bits indoors and lush landscaping outdoors will give you that tropical island feeling you are loo ...
From $466 per night (USD)VRBO
From $595 per night (USD)Expedia
~ CASABLANCA ~ Fabulous home w\/ private pool\/parking, in a quiet location.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Between the welcoming front porch and the private pool, you will be sure to enjoy fresh air and sunshine d ...
From $595 per night (USD)Expedia
From $2035 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 $2035 per night (USD)VRBO
From $425 per night (USD)Expedia
~ POINCIANA TREETOP ~ Casual second floor duplex 2 blocks from Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished second-floor duplex home comes with Key Wes ...
From $425 per night (USD)Expedia
From $1145 per night (USD)VRBO
Very Rare-The Galleon 3 King Bd, 3 Bath w\/ 4th king bd in loft + sleeper sofa
- Bedrooms:
- 3
- Bathrooms:
- 5
- 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 ...
From $1145 per night (USD)VRBO
From $222 per night (USD)Expedia
Old Town! Spacious Condo in Historic Home w\/Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into ...
From $222 per night (USD)Expedia
From $1288 per night (USD)VRBO
Havana Lane: An updated classic conch cottage with still a rustic edge!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enter the private courtyard of the home, to a lush tropical oasis. The large, free form pool with coral stone patio mak ...
From $1288 per night (USD)VRBO
From $359 per night (USD)Expedia
**MAISON TROPICALE @ OLD TOWN** Historic Home + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine a tra ...
From $359 per night (USD)Expedia
From $408 per night (USD)VRBO
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! This ultimate ...
From $408 per night (USD)VRBO
From $1196 per night (USD)Expedia
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + 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! Traveling to ...
From $1196 per night (USD)Expedia
From $2119 per night (USD)VRBO
**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 $2119 per night (USD)VRBO
From $518 per night (USD)Expedia
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finally, a la ...
From $518 per night (USD)Expedia
From $363 per night (USD)VRBO
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Part of a small collection of cottages known as The Colony, this quaint cottage sits to the back of the property and is ...
From $363 per night (USD)VRBO
From $343 per night (USD)Expedia
Quaint, Quiet & Convenient - CasaBianca is The Perfect Old Town Sanctuary
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to CasaBianca! Here you'll find the character & charm of Old Town blended perfectly with all the modern amenitie ...
From $343 per night (USD)Expedia
From $340 per night (USD)VRBO
**HAVANA HOUSE @ OLD TOWN** Elegant Cottage Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Located on So ...
From $340 per night (USD)VRBO
From $1325 per night (USD)Expedia
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For the ultim ...
From $1325 per night (USD)Expedia
From $2211 per night (USD)VRBO
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of a ...
From $2211 per night (USD)VRBO
From $1069 per night (USD)Expedia
Find Sanity in the Heart of Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the charm of this fantastic Old Town location surrounded by local businesses and restaurants, allowing you to ...
From $1069 per night (USD)Expedia