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 $257 per night (USD)
VRBO
La Hacienda in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Looking as though it were plucked from the glossy pages of Spanish literature, La Hacienda is one of Key West's most dis ...
From $257 per night (USD)
VRBO
From $561 per night (USD)
Expedia
Campbell Suite in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Let your rendezvous with paradise begin at the Campbell Courtyard compound in the heart of Old Town Key West. Campbell S ...
From $561 per night (USD)
Expedia
From $163 per night (USD)
VRBO
Bay's Hideaway in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just the mere idea of planning a vacation puts a smile on most faces. If your vacation includes a stay in the Conch Repu ...
From $163 per night (USD)
VRBO
From $814 per night (USD)
Expedia
Quilted Giraffe in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes yo ...
From $814 per night (USD)
Expedia
From $376 per night (USD)
VRBO
Florida | Waterfront 2BR/2BA w/ Pool + Dock Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just ...
From $376 per night (USD)
VRBO
From $318 per night (USD)
VRBO
Casa Bella Petite le Bleu - Luxury Key West Cottage w Pool - 2 Blocks Off Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
First impressions are everything. And it's love at first sight with the charming 2BR 2BA Casa Bella Petite le Bleu. This ...
From $318 per night (USD)
VRBO
From $304 per night (USD)
VRBO
Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Keys Please Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $304 per night (USD)
VRBO
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Expedia
Single home with pool, center of Old Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Beautiful, newly renovated single home of corner lot in the center of old town. 4 blocks from Duval and 4 blocks from se ...
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Expedia
$The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars$
From $619 per night (USD)
VRBO
The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy your tropical vacation, whether work-free or not, in this Old Town home only a couple of minutes from Duval and Wh ...
From $619 per night (USD)
VRBO
From $435 per night (USD)
Expedia
The Pinder House: Historic Charm w/ Pool, Steps from Duval St & the Seaport
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additi ...
From $435 per night (USD)
Expedia
From $1455 per night (USD)
VRBO
Designer Octagon House of Key West - w Private Pool - Blocks off Duval
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Standing prominently in the sought-after Key West Historic Seaport Neighborhood, this iconic Designer Octagon House of K ...
From $1455 per night (USD)
VRBO
From $1597 per night (USD)
Expedia
A Palm Tree Haven in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This lovely single-family, two-story luxury home is in the prestigious Truman Annex gated community on a very private cu ...
From $1597 per night (USD)
Expedia
From $2496 per night (USD)
VRBO
Harbor House Suite A | 4 Bed, 4 Bath
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Welcome to Luxury Harbor House Suites, an exceptional NIGHTLY vacation rental property located in the heart of Key West' ...
From $2496 per night (USD)
VRBO
From $282 per night (USD)
Expedia
UPTOWN FUNK ~ Newly Renovated 3 BR Townhome in Old Town with Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
IMMACULATE UPSCALE DELIGHT… Embrace the island vibes and immerse yourself in the Key West spirit in this enchanting 3 st ...
From $282 per night (USD)
Expedia
From $683 per night (USD)
VRBO
Ann Street Tranquility: A cozy and peaceful cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Stre ...
From $683 per night (USD)
VRBO
From $350 per night (USD)
VRBO
Old Town cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The newly remodeled home is located in the middle of Old Town down a private lane just a block from Duval Street. One of ...
From $350 per night (USD)
VRBO
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VRBO
Best Location -Hyatt Sunset Harbor- water view-Jan 26 to Feb 2. Seven nights
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
LISTING is ONLY available January 26 to Feb 2. Best location in town. Only 1.5 blocks to Duvall Street but quiet. Key We ...
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VRBO
From $641 per night (USD)
VRBO
Deluxe Key West Ocean Front Condo Week - April 22 - 29, 2025
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Deluxe Ocean Front Condo in Key West Florida with a spectacular 3rd Floor balcony view of the Marina and Ocean. One Full ...
From $641 per night (USD)
VRBO
From $2118 per night (USD)
VRBO
Luxury 4BDR/4BA Penthouse | 4 Bed, 4 Bath
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to the Luxury Harbor House Suites! We proudly offer you a newly renovated 2,400SF, 4BDR/4BA Penthouse in the Cit ...
From $2118 per night (USD)
VRBO
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Expedia
Priced to book! 2 Bdr/2Ba Walking distance to Duval St., Mallory Square, Trolley
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
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Expedia
From $254 per night (USD)
VRBO
Old Town Elegance with Island Breezes and Poolside Bliss
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Charming Pool Cottage in the Heart of Old Town Key West Perfectly situated in historic Old Town Key West, this quaint a ...
From $254 per night (USD)
VRBO
From $705 per night (USD)
Expedia
FERNWOOD ~ Dreamy, Lush Estate with Incredible Outdoor Space with Pool & Spa!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
THERE'S NO PLACE LIKE YOUR ISLAND HOME... Located in the highly sought-after area of The Meadows and beneath peaceful sw ...
From $705 per night (USD)
Expedia
From $3350 per night (USD)
VRBO
Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21
Bedrooms:
7
Bathrooms:
10
Sleeps:
21
The Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-s ...
From $3350 per night (USD)
VRBO
From $534 per night (USD)
Expedia
DOWNTOWN KEY WEST 2BED OCEANFRONT!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a great OCEANFRONT unit with large balcony to watch sunsets. Hyatt Sunset Harbor is perfectly located in downtow ...
From $534 per night (USD)
Expedia
From $882 per night (USD)
VRBO
Three Condos w/ Entertainment, Private Parking & Beach Nearby - Great for Groups
Bedrooms:
4
Bathrooms:
4
Sleeps:
14
Three Flowers Guesthouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $882 per night (USD)
VRBO
From $1712 per night (USD)
Expedia
Conch House in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Quintessential Grand Key West Estate! The James J. Curtis House c. 1874 was acquired by the Navy in 1903 and the home b ...
From $1712 per night (USD)
Expedia
From $132 per night (USD)
VRBO
Cubana Casita in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cubana Casita is an easy-access ground floor condo with one bedroom and 1 baths. This special home's 'from the ground up ...
From $132 per night (USD)
VRBO
From $181 per night (USD)
Expedia
The Sea Glass Cottage in Historic Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Spend time in beautiful Key West and live like a local in a true Conch Home! The Sea Glass Cottage is perfect for group ...
From $181 per night (USD)
Expedia
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VRBO
The Sandy Beach House in Historic Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Spend time in Key West and live like a local in a true Conch Home! The Sandy Beach Cottage, a fully-renovated first floo ...
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VRBO
From $238 per night (USD)
VRBO
Airy & Bright Home with Pool in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The perfect getaway for a long stay in Key West. A private pool and patio area lie behind a green gate on a quiet lane i ...
From $238 per night (USD)
VRBO
From $436 per night (USD)
VRBO
~ASHE HOUSE~ Renovated and relaxing with pool, porches, and privacy!
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 $436 per night (USD)
VRBO
From $162 per night (USD)
VRBO
Sunny Apartment with a Large Deck and Great View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming 1 bedroom second floor apartment with a large deck space for dining, sunbathing or watching sunsets. In residen ...
From $162 per night (USD)
VRBO
From $189 per night (USD)
VRBO
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
CLASSIC AND COZY... Exhale your worries away as you approach this delightful condo, one of four that are situated insid ...
From $189 per night (USD)
VRBO
From $544 per night (USD)
Expedia
BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w/ Pool, Spa & Exercise Room!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
OLD TOWN CLASSIC... This beautifully redesigned Conch house is in the heart of Key West. Located in the outstanding loc ...
From $544 per night (USD)
Expedia
From $596 per night (USD)
VRBO
**SOUL OF DUVAL @ DUVAL** Modern/Centrally Located + 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! There’s no do ...
From $596 per night (USD)
VRBO
From $411 per night (USD)
Expedia
THE WEEKEND HOUSE ~ 3 Bedroom, 2 Bath Condo Centrally Located w/ Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
WHERE LIFE IS PURE… This dreamy 3 bedroom, 2 bathroom island getaway is sure to captivate the true essence of Key West c ...
From $411 per night (USD)
Expedia
From $156 per night (USD)
VRBO
Adorable gated loft studio two blocks from Duval in Old Town - Location Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Sanctuary is tucked away on a quiet street just two blocks off Duval St. in Old Town Key West. This hidden gem is on ...
From $156 per night (USD)
VRBO
From $1117 per night (USD)
VRBO
Stunning Views at The Galleon Resort in Beautiful Key West! Charming 2 Bed!
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 $263 per night (USD)
VRBO
Ultimate Escape-2 bed 2 bath Old Town home, parking, open layout, Mid-century
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $263 per night (USD)
VRBO
From $1047 per night (USD)
Expedia
**THE GILDED PINEAPPLE @ THE SEAPORT** Gorgeous Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! THE GILDED PI ...
From $1047 per night (USD)
Expedia
From $382 per night (USD)
VRBO
Conch Cottage Retreat in the heart of Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Experience Old Town Key West in a classic conch home! This home is only steps from shopping, restaurants, the historic s ...
From $382 per night (USD)
VRBO
From $524 per night (USD)
Expedia
Two fully independent units in a Duplex, with independent entrances. One Rent!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to "Old Key West". Our Classic Old Town style duplex, with two independent fully renovated homes in the same pro ...
From $524 per night (USD)
Expedia
From $1044 per night (USD)
VRBO
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Elizabeth's Secret! You have found your secret! A very private and secluded tropical oasis awaits you behin ...
From $1044 per night (USD)
VRBO
From $649 per night (USD)
Expedia
Private Parking, Pool, Pet Friendly - Casa Azul
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Summary: Casa Azul is a luxe modern cottage with an open-concept living area that ends up filled with natural sunlight. ...
From $649 per night (USD)
Expedia
From $449 per night (USD)
VRBO
Ashe St Serenade: 3BD/3.5BA Luxury Retreat, Private Pool in an Island Oasis.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your dream getaway in the charming Old Town Key West, where the tranquility of island living meets the excite ...
From $449 per night (USD)
VRBO
From $669 per night (USD)
Expedia
Lavender on White - 3 BD /2 BA House w/ Private Heated Pool and great Kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Nestled in a prime location, Lavender on White offers the perfect blend of tranquility and accessibility. Situated in th ...
From $669 per night (USD)
Expedia
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VRBO
Priced to Book! 1BR/1BA Walking distance to Duval St.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
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VRBO
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Expedia
Key West “Blue Zone” Oasis with Pool, Pet Friendly
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Unwind and reconnect with nature at our tranquil VRBO property. As you enter the serene sanctuary, you'll be enveloped b ...
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Expedia
From $426 per night (USD)
VRBO
The Crystalmarine Suite – Rustic Luxury on the Sea
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Romantic getaway on the sea with panoramic views of the ocean. Capture each sunrise and sunset on board this one-of-a-ki ...
From $426 per night (USD)
VRBO
From $819 per night (USD)
Expedia
Private Heated Pool-2BR/2BA-OldTown Location-Avail Jan 1 -March 31 -Weekly Maid
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Charming house in Old town near the cemetery and 3 blocks from Duval. Complete renovation with Central Air, full design ...
From $819 per night (USD)
Expedia
From $555 per night (USD)
VRBO
AMBER COTTAGE ~ Renovated 3 Bedroom, 3.5 Bathroom Home w/ Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
AN ISLAND STUNNER... This is the back cottage of the delightful Jewel Box Cottages compound, located in Old Town, just s ...
From $555 per night (USD)
VRBO
From $430 per night (USD)
Expedia
PEARL COTTAGE ~ 3 Bedroom, 3.5 Bathroom Home with Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
CONCH STYLE CHARM... This is the front cottage of the delightful Jewel Box Cottage compound, located in Old Town, just a ...
From $430 per night (USD)
Expedia
From $1028 per night (USD)
VRBO
JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w/ Private Pools!
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
BEDAZZLING COMPOUND... Two delightful conch style island homes are situated on one glorious parcel in Old Town, just a s ...
From $1028 per night (USD)
VRBO
From $167 per night (USD)
Expedia
Prime Old Town Location w/ Pool, Walk to Duval Steet | Blue Heron by AvantStay
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*This condo is available for 28+ day stays only, and the pool area is shared with 3 other condos.* Located at 906-2 Tru ...
From $167 per night (USD)
Expedia
From $794 per night (USD)
VRBO
The Caroline Suite | 1 bed, 1 bath condo w/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover your perfect island escape at The Caroline Suite, a recently refreshed 1 bedroom, 1 bathroom nightly vacation r ...
From $794 per night (USD)
VRBO
From $1778 per night (USD)
VRBO
The Cathouse, an Old Town tropical poolside oasis with huge, heated pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Relax in this tropical poolside townhouse in the heart of Key West. Wake up surrounded by lush tropical landscaping and ...
From $1778 per night (USD)
VRBO
From $2981 per night (USD)
VRBO
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
The iconic William Skelton Home in downtown Key West offers an ideal retreat for your group of 16 guests. The six bedroo ...
From $2981 per night (USD)
VRBO
From $746 per night (USD)
Expedia
**TRUMAN’S TROVE @ THE ANNEX** Private Home & 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! Hunting for t ...
From $746 per night (USD)
Expedia
From $505 per night (USD)
VRBO
Paradise found! 2 br/1 bth restored Old Town home with private cocktail pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Fully renovated and furnished 2 bedroom,1 bath cottage in a lovely tropical setting across from the cemetery in Old Town ...
From $505 per night (USD)
VRBO
From $1164 per night (USD)
Expedia
Kemp House in Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of ...
From $1164 per night (USD)
Expedia
From $256 per night (USD)
VRBO
Charming + Circa 1889 Historic Eyebrow Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
28 Night Minimum. Welcome to "The Saltbox"! Featured in design magazines. 710 Ashe Street is a charming house circa 18 ...
From $256 per night (USD)
VRBO
From $1134 per night (USD)
VRBO
Angela’s Conch Cottage - Old Town “Extraordinary home & heated pool”
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Angela’s Conch Cottage, as seen on HG TV's House Hunters, is located in the heart of Old Town Key West, across from the ...
From $1134 per night (USD)
VRBO
From $894 per night (USD)
VRBO
SEAPORT PANORAMA-Beach-Pool-King-BBQ-Kitchen views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY V ...
From $894 per night (USD)
VRBO
From $471 per night (USD)
Expedia
The Elizabeth Suite | 1 bed, 1 bath w/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience the charm of historic Key West with a stay at The Elizabeth Suite, a recently renovated 1 bedroom, 1 bathroom ...
From $471 per night (USD)
Expedia
From $402 per night (USD)
VRBO
The Fleming Suite | 1 bed, 1 bath condo w/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to The Fleming Suite, a 1 bedroom, 1 bathroom vacation rental located at The Bayview House in vibrant Key West. ...
From $402 per night (USD)
VRBO
From $262 per night (USD)
VRBO
Breezy Key West First-Floor Condo w/ Pool Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience your next seaside vacation in style at this 2-bedroom, 2-bathroom Key West vacation rental. This 1st-floor co ...
From $262 per night (USD)
VRBO
From $803 per night (USD)
VRBO
Key West Andros 2BR•Waterfront, Pool, Dock&Pet OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Time to fish, relax, and unwind! Bring your family & friends to this spacious 1,350 sqft waterfront corner cond ...
From $803 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Our Piece of Paradise-
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your ideal Key West getaway! Perfect for families and ideally situated between Old Town, New Town, and Duval ...
From $402 per night (USD)
Expedia
From $631 per night (USD)
VRBO
Midnight Cowboy by AvantStay | 3 Artistic Spaces
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-ti ...
From $631 per night (USD)
VRBO
From $248 per night (USD)
Expedia
Tennessee Williams by AvantStay | Funky Design + Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Tennessee Williams is a one-of-a-kind Key West esca ...
From $248 per night (USD)
Expedia
From $1033 per night (USD)
VRBO
Rooftop Penthouse, Walk to Duval - KAMP
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $1033 per night (USD)
VRBO
From $325 per night (USD)
Expedia
Bohemian island home full of color and modern amenities - in a great location
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Casa Del Sol Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $325 per night (USD)
Expedia
From $575 per night (USD)
VRBO
Experience The Galleon – A 5-Star Timeshare Resort in Charming Old Key West, Fl
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to The Galleon Resort, ideally situated in the heart of Old Town Key West on the historic Seaport/Marina—just a ...
From $575 per night (USD)
VRBO
Click For Pricing
Expedia
Beautifully decorated home located in the White Street Gallery District.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
On The Rocks is a beautifully renovated and decorated home located in the White Street Gallery District. It combines the ...
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Expedia
From $356 per night (USD)
VRBO
TURTLE HOUSE a dream come true!
Bedrooms:
2
Bathrooms:
2
Sleeps:
3
Turtle House. A Key West Artist's oasis. Now available for March 2023. Easter in Key West! Delight in the uniquene ...
From $356 per night (USD)
VRBO
From $180 per night (USD)
VRBO
STUNNING! HEART OF OLD TOWN!: Walk to Duval and Historic Seaport in minutes.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Live like a local in this unique loft apartment in the heart of Key West's Old Town historic district. Walk to Duval Str ...
From $180 per night (USD)
VRBO
From $680 per night (USD)
VRBO
NEW MONTHLY LISTING! Seacret Paradise: Desirable Oasis in the Heart of Old Town
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Charming Key West Oasis - Perfect Blend of Tranquility and Vibrancy! Escape to a hidden gem nestled on a serene lane be ...
From $680 per night (USD)
VRBO
From $4836 per night (USD)
VRBO
Quaint Key West Getaway: Historic Knowles House w/Private Pool & Rooftop Deck
Bedrooms:
8
Bathrooms:
7
Sleeps:
16
Short walk to Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. 7 to 8 rooms with ens ...
From $4836 per night (USD)
VRBO
From $1524 per night (USD)
VRBO
Truman House in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home w ...
From $1524 per night (USD)
VRBO
From $508 per night (USD)
Expedia
Bring your umbrella drinks @Tiki Beach Too! Shipyard 2bed/2bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your perfect tropical retreat in the heart of Key West, Florida! Nestled within the renowned Shipyard condomi ...
From $508 per night (USD)
Expedia
From $498 per night (USD)
VRBO
MIMOSAS ON PINE ~ 3 Bedroom 2.5 Bath Home w/Pool & Great Spring/Summer Deals!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
YOUR STORYBOOK COTTAGE... This island delight is tucked away on a vibrant and secluded street of The Meadows neighborhoo ...
From $498 per night (USD)
VRBO
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 $402 per night (USD)
VRBO
Snowbird-friendly oasis with private heated pool, lush yard, & ample parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
The Orchid House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $402 per night (USD)
VRBO
From $1068 per night (USD)
Expedia
3 Bedroom Key West Home - Perfect Location & Private Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The historic William Skelton Home is ideally located on Eaton Street in Old Town Key West, steps from Duval Street, hund ...
From $1068 per night (USD)
Expedia
From $1217 per night (USD)
VRBO
**SPIRIT OF KEY WEST @ OLD TOWN** Exquisite 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! SPIRIT OF KEY ...
From $1217 per night (USD)
VRBO
From $525 per night (USD)
Expedia
The Cozy Little Cottage!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to The Cozy Little Cottage !!! A REAL ISLAND GATAWAY IN KEY WEST!!! Nested in the heart of Key West, The Cozy L ...
From $525 per night (USD)
Expedia
From $413 per night (USD)
VRBO
Beautiful Old Town 2 bedroom Cottage on a Private Lane
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Located in the heart of Key West's historic district on a quiet lane with parking directly in front of the private gated ...
From $413 per night (USD)
VRBO
From $426 per night (USD)
VRBO
Winter Months Open Frogmore on Fleming in Downtown Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your dream residence in the heart of Key West, Florida! Nestled in a prime location, this 2-bedroom apartment ...
From $426 per night (USD)
VRBO
$ALL INCLUSIVE! Snorkel/Sail/Spear Fish/Fishing/Fun\n$
Click For Pricing
VRBO
ALL INCLUSIVE! Snorkel/Sail/Spear Fish/Fishing/Fun\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
You will love staying on this 45' GulfStar Sloop. The boat boasts 2 BR, 1.5 bath with shower, full working galley, A/C t ...
Click For Pricing
VRBO
From $196 per night (USD)
Expedia
Dog-friendly condo near beach with pool, grill, outdoor shower, W/D, AC
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Paradise on Packer Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $196 per night (USD)
Expedia
From $862 per night (USD)
VRBO
The Perch on Duval- Hip & Modern Duval Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to Perch on Duval, an elegant and charming 2-bedroom vacation rental situated in the heart of downtown Key West. ...
From $862 per night (USD)
VRBO
From $152 per night (USD)
Expedia
Large 1 bedroom condo in the historic area of Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy your Key West vacation in this spacious 623 square foot condo located on the second floor of this classical reviva ...
From $152 per night (USD)
Expedia
From $2930 per night (USD)
VRBO
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
NEW LISTINGS APRIL - 2024! Welcome to the Pagitt House built in 1933 and located on Elizabeth Street just steps to all ...
From $2930 per night (USD)
VRBO
Click For Pricing
Expedia
Studio Unit in quiet resort adjacent to Old Town Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
With a coveted location in the heart of Old Town and magnificent views of the Gulf of Mexico, Sunset Harbor is the ultim ...
Click For Pricing
Expedia
$Escape to \Casa Escondida\$
From $579 per night (USD)
VRBO
Escape to \"Casa Escondida\"
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to the enchanting "Casa Escondida," a historic Conch Style home with a modern twist, nestled on a tranquil, seclu ...
From $579 per night (USD)
VRBO
From $3877 per night (USD)
VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to The Galleon Resort in Key West, where paradise meets luxury at the southernmost tip of the United States. In ...
From $3877 per night (USD)
VRBO
From $312 per night (USD)
VRBO
Bohemian Retreat with Pool in Old Town Key West | Free Breakfast Onsite!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $312 per night (USD)
VRBO
From $480 per night (USD)
VRBO
Romantic Key West Getaway with Heated Pool, Patio & Breakfast | Near Sunset Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $480 per night (USD)
VRBO
From $446 per night (USD)
VRBO
Quaint Bungalow w/ Private Outdoor Space Near Duval Street | Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $446 per night (USD)
VRBO
From $528 per night (USD)
VRBO
Celebrate History in Key West: Tropical Free Breakfast and Pool Access!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $528 per night (USD)
VRBO

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