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 $1725 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 $1725 per night (USD)
VRBO
From $1117 per night (USD)
VRBO
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 $1117 per night (USD)
VRBO
From $1147 per night (USD)
VRBO
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Bottom’s Up Bungalow — Your Private Tropical Escape in Old Town Key West Step into a world of comfort and is ...
From $1147 per night (USD)
VRBO
From $898 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 $898 per night (USD)
VRBO
From $1473 per night (USD)
VRBO
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $1473 per night (USD)
VRBO
From $208 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 $208 per night (USD)
Expedia
From $667 per night (USD)
VRBO
**OLD TOWN OASIS @ THE ANNEX** Oceanside 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! OLD TOWN OASI ...
From $667 per night (USD)
VRBO
From $1996 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 $1996 per night (USD)
Expedia
From $849 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 $849 per night (USD)
VRBO
From $430 per night (USD)
VRBO
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 $430 per night (USD)
VRBO
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
From $516 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 $516 per night (USD)
Expedia
From $650 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 $650 per night (USD)
VRBO
From $658 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 $658 per night (USD)
VRBO
From $574 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 $574 per night (USD)
VRBO
From $248 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 $248 per night (USD)
VRBO
From $514 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 $514 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 $465 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 $465 per night (USD)
VRBO
From $587 per night (USD)
VRBO
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 $587 per night (USD)
VRBO
From $278 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 $278 per night (USD)
VRBO
From $659 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 $659 per night (USD)
VRBO
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 $459 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 $459 per night (USD)
Expedia
From $650 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 $650 per night (USD)
VRBO
From $568 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 $568 per night (USD)
Expedia
From $603 per night (USD)
VRBO
Miami Vice Sailboat Used For TV Series we moved out of the Perry Marina
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
We are working on renovations other repairs. We are taking a limited number of day sails and plan to retire. Please chec ...
From $603 per night (USD)
VRBO
From $511 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 $511 per night (USD)
Expedia
From $586 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 $586 per night (USD)
VRBO
From $322 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 $322 per night (USD)
Expedia
From $463 per night (USD)
VRBO
2 Bedroom 1 Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $463 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 Pricing
Expedia
From $1216 per night (USD)
VRBO
Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites & Marina - NO CLEANING FEE
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1216 per night (USD)
VRBO
From $833 per night (USD)
Expedia
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 $833 per night (USD)
Expedia
From $210 per night (USD)
VRBO
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 $210 per night (USD)
VRBO
From $433 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 $433 per night (USD)
VRBO
From $497 per night (USD)
VRBO
~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 $497 per night (USD)
VRBO
From $742 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 $742 per night (USD)
VRBO
From $572 per night (USD)
VRBO
~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 $572 per night (USD)
VRBO
From $2667 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 $2667 per night (USD)
VRBO
From $585 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 $585 per night (USD)
VRBO
From $1296 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 $1296 per night (USD)
VRBO
$Historic \Old Town\ Charm$
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
From $912 per night (USD)
Expedia
3-Bedroom 3-Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $912 per night (USD)
Expedia
From $1047 per night (USD)
VRBO
Waterfront 4-Bed, 4-Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE
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 $1090 per night (USD)
Expedia
4-Bed 4.5 Bath Condo @ Bayfront Suites - NO CLEANING FEE (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 $1090 per night (USD)
Expedia
From $746 per night (USD)
VRBO
3 Bed 3 Bath Condo @ Bayfront Suites - NO CLEANING FEE (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 $746 per night (USD)
VRBO
From $1055 per night (USD)
Expedia
4-Bed, 3-Bath Waterfront Condo at Bayfront Suites & Marina - NO CLEANING FEE
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1055 per night (USD)
Expedia
From $1190 per night (USD)
VRBO
4-Bed, 4.5 Bath Condo & Bayfront Suites - NO CLEANING FEE (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 $1190 per night (USD)
VRBO
From $771 per night (USD)
Expedia
Waterfront 3-Bedroom Condo at Bayfront Suites & Marina - NO CLEANING FEE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $771 per night (USD)
Expedia
From $203 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 $203 per night (USD)
VRBO
From $267 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 $267 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
Bedrooms:
2
Bathrooms:
3
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 $215 per night (USD)
VRBO
From $610 per night (USD)
VRBO
Key West 44ft Sailboat Wild Thing-we are moving !
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We are moving ! Check for details here! Will be retiring and will take limited number of custom sailing trips. Located ...
From $610 per night (USD)
VRBO
From $291 per night (USD)
VRBO
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 $291 per night (USD)
VRBO
From $529 per night (USD)
Expedia
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 $529 per night (USD)
Expedia
$The Hollinsed House \Victorian Delights\ - Large 1 Bedroom$
From $327 per night (USD)
VRBO
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 $327 per night (USD)
VRBO
From $1034 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 $1034 per night (USD)
VRBO
From $864 per night (USD)
VRBO
~ 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 $864 per night (USD)
VRBO
From $329 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 $329 per night (USD)
VRBO
From $1119 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 $1119 per night (USD)
VRBO
From $1218 per night (USD)
Expedia
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 $1218 per night (USD)
Expedia
From $534 per night (USD)
VRBO
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 $534 per night (USD)
VRBO
From $372 per night (USD)
Expedia
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 $372 per night (USD)
Expedia
From $516 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 $516 per night (USD)
VRBO
From $904 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 $904 per night (USD)
VRBO
From $489 per night (USD)
VRBO
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 $489 per night (USD)
VRBO
From $1880 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 $1880 per night (USD)
VRBO
From $501 per night (USD)
VRBO
~ 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 $501 per night (USD)
VRBO
From $1473 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 $1473 per night (USD)
VRBO
From $713 per night (USD)
VRBO
~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
**This home is available in August only as a monthly rental (28 nights in the same month).** Come and live like a local! ...
From $713 per night (USD)
VRBO
From $461 per night (USD)
Expedia
~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 $461 per night (USD)
Expedia
From $490 per night (USD)
VRBO
~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 $490 per night (USD)
VRBO
From $560 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 $560 per night (USD)
VRBO
From $967 per night (USD)
VRBO
~ 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 $967 per night (USD)
VRBO
From $2281 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 $2281 per night (USD)
VRBO
From $411 per night (USD)
VRBO
~ 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 $411 per night (USD)
VRBO
From $1386 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 $1386 per night (USD)
VRBO
From $181 per night (USD)
VRBO
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 $181 per night (USD)
VRBO
From $1439 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 $1439 per night (USD)
VRBO
From $483 per night (USD)
VRBO
**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 $483 per night (USD)
VRBO
From $607 per night (USD)
Expedia
**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 $607 per night (USD)
Expedia
From $920 per night (USD)
VRBO
**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 $920 per night (USD)
VRBO
From $2524 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 $2524 per night (USD)
Expedia
From $775 per night (USD)
VRBO
**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 $775 per night (USD)
VRBO
From $557 per night (USD)
VRBO
COLONY CALYPSO - A quaint 1 Bedroom Cottage just two blocks to Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Part of a small collection of cottages known as The Colony, this quaint cottage sits to the back of the property and is ...
From $557 per night (USD)
VRBO
Click For Pricing
VRBO
Hyatt Sunset Harbor on the Water-Luxury Key West 2 Bedroom Condo Dec 21-Dec 28.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is the luxury boutique resort you and your family and friends deserve. A few steps to famous Mallory Square and all ...
Click For Pricing
VRBO
From $435 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 $435 per night (USD)
Expedia
From $391 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 $391 per night (USD)
VRBO
From $1086 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 $1086 per night (USD)
Expedia
From $2467 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 $2467 per night (USD)
VRBO
From $988 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 $988 per night (USD)
Expedia
From $964 per night (USD)
VRBO
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This precious ...
From $964 per night (USD)
VRBO
From $2011 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 $2011 per night (USD)
Expedia
From $636 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 $636 per night (USD)
VRBO
From $1333 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 $1333 per night (USD)
Expedia
From $955 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 $955 per night (USD)
VRBO
From $283 per night (USD)
Expedia
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Jasmine Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $283 per night (USD)
Expedia
From $325 per night (USD)
VRBO
Breezy Florida Home with Shared Pool, Dog & Snowbird-Friendly - Walk to Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Conched Out Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $325 per night (USD)
VRBO
From $457 per night (USD)
Expedia
Sunny condo with pool, lovely deck, central AC & washer/dryer - central location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Oceana Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $457 per night (USD)
Expedia

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