Fleming Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Fleming Key, Florida on RentalSaver.com!

Fleming Key Rentals

From $1190 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 $1190 per night (USD)
VRBO
From $889 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 $889 per night (USD)
Expedia
Click For Pricing
VRBO
JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West. A true guest favorite with over 1 ...
Click For Pricing
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $1183 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 $1183 per night (USD)
VRBO
From $299 per night (USD)
Expedia
Private Home in Heart of Old Town (Shared Pool!)
Bedrooms:
1
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 $449 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 $449 per night (USD)
VRBO
From $1988 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 $1988 per night (USD)
Expedia
From $872 per night (USD)
VRBO
SEAPORT SKYLINE-Beach-Pool-King-BBQ-Hot Tub-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)
VRBO
From $376 per night (USD)
Expedia
The Caribbean Suite - 2-K-bedroom /1 bath/ kitchenette/sleeps 6
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This deluxe "Key West Charmer" is a beautifully restored Victorian home built in the 1880's that was converted into indi ...
From $376 per night (USD)
Expedia
Click For Pricing
VRBO
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 Pricing
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $662 per night (USD)
VRBO
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
2
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)
VRBO
From $423 per night (USD)
Expedia
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 $423 per night (USD)
Expedia
From $455 per night (USD)
VRBO
Welcome to the Shady Palms - Private Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $455 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $422 per night (USD)
VRBO
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 $422 per night (USD)
VRBO
From $784 per night (USD)
Expedia
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 $784 per night (USD)
Expedia
From $242 per night (USD)
VRBO
Heavenly Hideaway-Monthly 3BD 2.5BA Private Pool - RealKeyWest
Bedrooms:
0
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 $242 per night (USD)
VRBO
From $306 per night (USD)
Expedia
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $306 per night (USD)
Expedia
From $271 per night (USD)
VRBO
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 $271 per night (USD)
VRBO
From $444 per night (USD)
Expedia
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 $444 per night (USD)
Expedia
From $811 per night (USD)
VRBO
Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!
Bedrooms:
4
Bathrooms:
4
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)
VRBO
From $370 per night (USD)
Expedia
THE FICUS HOUSE ~ Adult Only, Lush 3 BR, 2.5 Ba Gem with Pool and Cottage!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
VINTAGE ISLAND PARADISE... Tucked within luxuriant foliage lies this timeless, adult only, tropical sanctuary in the mid ...
From $370 per night (USD)
Expedia
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 $431 per night (USD)
Expedia
PURA VIDA ~ 3 Bed/3.5 Bath Home on Quaint Old Town Lane!
Bedrooms:
3
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 $431 per night (USD)
Expedia
From $609 per night (USD)
VRBO
Miami Vice Sailboat Used For TV Series with 2 Hour Sandbar Motor Boat Trip
Bedrooms:
1
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 $609 per night (USD)
VRBO
From $341 per night (USD)
Expedia
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + 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! It is not so ...
From $341 per night (USD)
Expedia
From $615 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 $615 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Runaway Bills | 3 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This stylish Conch Home is tucked away on a quiet lane in Old Town Key West. Surrounded by distinctive neighborhoods thi ...
From $356 per night (USD)
Expedia
From $379 per night (USD)
VRBO
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 $379 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 $943 per night (USD)
VRBO
Waterfront 4 Bed, 4-Bath Condo @ 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 $943 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 $1006 per night (USD)
VRBO
Downtown Retreat - A++ Location W/ Private Heated Pool/Hot Tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in ...
From $1006 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 $300 per night (USD)
VRBO
~ VILLA AZUL ~ Enjoy this historic home with pool house and parking.
Bedrooms:
2
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 $300 per night (USD)
VRBO
From $385 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 $385 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $386 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 $386 per night (USD)
Expedia
From $1666 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 $1666 per night (USD)
VRBO
Click For Pricing
Expedia
Waterfront 4-Bedroom 3-Bath 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 ...
Click For Pricing
Expedia
From $543 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 $543 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
$Historic \Old Town\ Charm$
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
Click For Pricing
Expedia
3-Bedroom 3-Bath 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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Waterfront 4-Bed, 4-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 ...
Click For Pricing
VRBO
From $811 per night (USD)
Expedia
4-Bed 4.5 Bath Condo @ Bayfront Suites & Marina Non-Waterfront
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $811 per night (USD)
Expedia
From $735 per night (USD)
VRBO
3 Bedroom Condo at Bayfront Suites & Marina - Non-Waterfront
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $735 per night (USD)
VRBO
From $843 per night (USD)
Expedia
4-Bed, 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 $843 per night (USD)
Expedia
From $883 per night (USD)
VRBO
4-Bed, 4.5 Bath Condo at Bayfront Suites & Marina Non-Waterfront
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $883 per night (USD)
VRBO
From $700 per night (USD)
Expedia
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 $700 per night (USD)
Expedia
From $148 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 $148 per night (USD)
VRBO
From $331 per night (USD)
Expedia
Hidden Treasure in Old Town: 3BR Home with Pool in Peaceful Gated Enclave
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Your Key West Hideaway home is located in the heart of Old Town. Key West landmarks, attractions, Duval St, restaurants, ...
From $331 per night (USD)
Expedia
From $216 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 $216 per night (USD)
VRBO
From $286 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 $286 per night (USD)
Expedia
From $523 per night (USD)
VRBO
Key West 44ft Sailboat Wild Thing-Summer Fun Sandbar Motorboat Trips
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Boats are located at the Perry Marina! Summer special starting 6/1/25 until 10/1/25 receive upon weather availability-a ...
From $523 per night (USD)
VRBO
From $315 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 $315 per night (USD)
Expedia
From $454 per night (USD)
VRBO
LOVE LANDING ~ Charming 3 Bedroom, 3 Bathroom Home w/ Pool and Parking!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
MARITIME-INSPIRED LIVING… Come unwind in this desirable retreat, tucked in a quiet and private lane just a stone's throw ...
From $454 per night (USD)
VRBO
$The Hollinsed House \Victorian Delights\ - Large 1 Bedroom$
From $297 per night (USD)
Expedia
The Hollinsed House \"Victorian Delights\" - Large 1 Bedroom
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Mingle with other guests around the tropical gardens surrounding the heated pool and sundeck creating the perfect settin ...
From $297 per night (USD)
Expedia
From $697 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 $697 per night (USD)
VRBO
From $538 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 $538 per night (USD)
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $652 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 $652 per night (USD)
Expedia
From $947 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 $947 per night (USD)
VRBO
From $448 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 $448 per night (USD)
Expedia
From $279 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 $279 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $670 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 $670 per night (USD)
VRBO
From $316 per night (USD)
Expedia
WANDERLUST ~ Stunning 3 Bed, 3 Bath Retreat in Peaceful Neighborhood w/ Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
STUNNING KEY WEST RETREAT… Just renovated, this island gem exudes the utmost island spirit with authentic historic chara ...
From $316 per night (USD)
Expedia
From $829 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 $829 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $967 per night (USD)
VRBO
~ SOUTHARD COMFORT ~ Feel the Key West vibe in Old Town with a private pool.
Bedrooms:
2
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 $967 per night (USD)
VRBO
From $373 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 $373 per night (USD)
Expedia
From $356 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 $356 per night (USD)
VRBO
From $478 per night (USD)
Expedia
~TROPICAL DREAM~Sun deck, pool, and parking adorn this home in Old Town.
Bedrooms:
4
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 $478 per night (USD)
Expedia
From $347 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 $347 per night (USD)
VRBO
From $614 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 $614 per night (USD)
Expedia
From $1455 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 $1455 per night (USD)
VRBO
From $343 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 $343 per night (USD)
Expedia
From $1182 per night (USD)
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 ...
From $1182 per night (USD)
VRBO
From $215 per night (USD)
Expedia
Old Town! Spacious Condo in Historic Home w/Pool!
Bedrooms:
2
Bathrooms:
1
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 $215 per night (USD)
Expedia
From $1285 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 $1285 per night (USD)
VRBO
From $313 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 $313 per night (USD)
Expedia
From $619 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 $619 per night (USD)
VRBO
From $682 per night (USD)
Expedia
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + 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! Traveling to ...
From $682 per night (USD)
Expedia
From $1651 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 $1651 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
Bedrooms:
1
Bathrooms:
1
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 ...
Click For Pricing
VRBO
From $336 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 $336 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 $932 per night (USD)
Expedia
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For the ultim ...
From $932 per night (USD)
Expedia
From $1860 per night (USD)
VRBO
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of a ...
From $1860 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + 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! This precious ...
Click For Pricing
VRBO
From $1291 per night (USD)
Expedia
**CASA VICTORIA @ OLD TOWN** Historic 5BR 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! CASA VICTORIA ...
From $1291 per night (USD)
Expedia
From $453 per night (USD)
VRBO
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate 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! For many, the ...
From $453 per night (USD)
VRBO
From $672 per night (USD)
Expedia
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + 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! Traveling to ...
From $672 per night (USD)
Expedia
From $770 per night (USD)
VRBO
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The high-end sophisticated Rooftop Penthouse is located directly above the famous Wyland Gallery on Duval Street. Enjoy ...
From $770 per night (USD)
VRBO
From $609 per night (USD)
Expedia
Poolside Suite with 1 Bedroom, 1 Bath with Kitchen and Pullout Sofa
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A beautifully renovated suite featuring a living room with a queen sofa bed, a modern kitchenette and a spacious master ...
From $609 per night (USD)
Expedia

Search Your Destination Now!

Fleming Key Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 794 Rentals