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 $405 per night (USD)
VRBO
Sunshine Siesta Cottage~Great Old Town Location, Pool, Private Hot Tub!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
BOOK NOW! Walk down the secluded brick path of the 4-unit compound, past the tropical foliage to Unit B, adjacent to the ...
From $405 per night (USD)
VRBO
From $462 per night (USD)
Expedia
**MARGARET’S MAGIC COMPOUND @ SOLARIS HILL** Old Town Compound & Pool + LAST KEY
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Travelers fro ...
From $462 per night (USD)
Expedia
From $707 per night (USD)
VRBO
Eliza's Secret - Elegant Tropical Oasis with Private Pool & Guest House
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Enjoy all of Key West's exciting activities from the privacy and comfort of your own two-story, historic home in Old Tow ...
From $707 per night (USD)
VRBO
From $147 per night (USD)
Expedia
Campbell Cottage in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location...Location...Location! Campbell Cottage is perfectly located to walk to almost everything Key West has to offer ...
From $147 per night (USD)
Expedia
From $374 per night (USD)
VRBO
The Courtyard in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can ...
From $374 per night (USD)
VRBO
From $183 per night (USD)
Expedia
Anchor's Away in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Need a refresher course in relaxation? Find it behind the brass seahorse knocker on the front door of this three-bedroom ...
From $183 per night (USD)
Expedia
From $470 per night (USD)
VRBO
Coral Condo in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom ...
From $470 per night (USD)
VRBO
From $240 per night (USD)
Expedia
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 $240 per night (USD)
Expedia
From $374 per night (USD)
VRBO
Campbell Suite in Key West
Bedrooms:
2
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 $374 per night (USD)
VRBO
From $92 per night (USD)
Expedia
Bay's Hideaway in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summer Discounts!Just the mere idea of planning a vacation puts a smile on most faces. If your vacation includes a stay ...
From $92 per night (USD)
Expedia
From $654 per night (USD)
VRBO
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 $654 per night (USD)
VRBO
From $235 per night (USD)
Expedia
MONTHLY - 1 block from the Seaport and 2 blocks from Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This beautifully decorated property has soaring ceilings with a lovely outdoor dining & bbq area and is walking distance ...
From $235 per night (USD)
Expedia
From $166 per night (USD)
VRBO
Conch Republic Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summer Discounts!This historic conch home, circa 1890, is your dream vacation spot. The welcoming property has been comp ...
From $166 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Old Town Classic with plenty of charm, porch swing and parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Beautiful home with covered porch and swing! Full kitchen, washer/dryer, TV, Internet, A/C, separate patio area with twi ...
From $409 per night (USD)
Expedia
$\A Bird's Eye View\ at The Truman Annex in Key West$
From $393 per night (USD)
VRBO
\"A Bird's Eye View\" at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Stunning, Modern 2 bedroom, 1 bathroom second floor condo in the Truman Annex Shipyard Complex completely renovated. Ful ...
From $393 per night (USD)
VRBO
From $184 per night (USD)
Expedia
Land Of Love by AvantStay | Pets Allowed! Shared Pool! Great Location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Your perfect escape to Key West awaits you in the L ...
From $184 per night (USD)
Expedia
From $188 per night (USD)
VRBO
Boat House by AvantStay | Character Cottage | Central Location Month Long Stays
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
*Please note that this home is available for 28+ night stays only.* Step into a tranquil community on a quiet lane and ...
From $188 per night (USD)
VRBO
$Ibis by AvantStay | Close to Duval Street w\/ Shared Pool | Month Long Stays Only$
From $193 per night (USD)
Expedia
Ibis by AvantStay | Close to Duval Street w\/ Shared Pool | Month Long Stays Only
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*Please note that this home is available for 28+ night stays only.* Enjoy your private front porch in this quiet neighb ...
From $193 per night (USD)
Expedia
$Easy Livin' by AvantStay | Key West Home w\/ Pool & BBQ | Week Long Stays Only$
From $1079 per night (USD)
VRBO
Easy Livin' by AvantStay | Key West Home w\/ Pool & BBQ | Week Long Stays Only
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $1079 per night (USD)
VRBO
$Artist Garden by AvantStay | Great Location w\/ Balcony, Shared Pool & BBQ!$
From $565 per night (USD)
Expedia
Artist Garden by AvantStay | Great Location w\/ Balcony, Shared Pool & BBQ!
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
*Please note that this home is available for stays of 7+ days only. Starting January 1, 2026, it will be available for s ...
From $565 per night (USD)
Expedia
$Paradise Palms by AvantStay | Great Location w\/ Outdoor Dining, BBQ$
From $192 per night (USD)
VRBO
Paradise Palms by AvantStay | Great Location w\/ Outdoor Dining, BBQ
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Make your next Florida vacation something special w ...
From $192 per night (USD)
VRBO
$First Breath by AvantStay | Close to Old Town w\/ Pool | Month Long Stays Only$
From $327 per night (USD)
Expedia
First Breath by AvantStay | Close to Old Town w\/ Pool | Month Long Stays Only
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*Please note that this home is available for 28+ night stays only.* Bring the family to this 3 bed, 2 bath private conc ...
From $327 per night (USD)
Expedia
$Casa de Rosalie by AvantStay | Great Location w\/ Pool, BBQ & Outdoor Dining$
From $319 per night (USD)
VRBO
Casa de Rosalie by AvantStay | Great Location w\/ Pool, BBQ & Outdoor Dining
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
*Please note that this home is available for 28+ night stays only.* Built-in 1889 with original Dade County Pine, histo ...
From $319 per night (USD)
VRBO
From $225 per night (USD)
Expedia
Lazy Gecko by AvantStay | Walk to Duval St in Key West! | Month Long Stays Only
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Grab your bike and head for some fresh seafood at t ...
From $225 per night (USD)
Expedia
Click For Pricing
VRBO
Priced to book! Sleeps 4- Walking Distance to Duval!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
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VRBO
$Amazing Location 3bed\/2bath & Swim Spa\n\n$
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Expedia
Amazing Location 3bed\/2bath & Swim Spa\n\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Fully furnished ground floor cottage with 3 bedrooms (queen bed in each), 2 full bathrooms, plus a loft with an addition ...
Click For Pricing
Expedia
From $4210 per night (USD)
VRBO
Combined Bayview Manor and Bayview Retreat, accommodating up to 22 guests!
Bedrooms:
7
Bathrooms:
9
Sleeps:
22
Enjoy the comfort of accommodating up to 22 guests, in beds, over two luxury waterfront homes on Garrison Bight! Central ...
From $4210 per night (USD)
VRBO
From $1550 per night (USD)
Expedia
Bayview Manor at Paradise Harbor with Private Pool and Dock!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $1550 per night (USD)
Expedia
From $640 per night (USD)
VRBO
NEW MONTHLY LISTING! Seacret Paradise: Desirable Oasis in the Heart of Old Town
Bedrooms:
4
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 $640 per night (USD)
VRBO
$Quaint Key West Getaway: Historic Knowles House w\/Private Pool & Rooftop Deck$
From $3012 per night (USD)
Expedia
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 $3012 per night (USD)
Expedia
From $1204 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 $1204 per night (USD)
VRBO
Click For Pricing
Expedia
OLD TOWN LUXURY HOME - completely remodeled, updated, steps to Duval Street.
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Located in the heart of Old Town, this rare home has 3 Bedrooms with 3.5 Baths in the Main House. New in 2021 to the hig ...
Click For Pricing
Expedia
From $201 per night (USD)
VRBO
Lazy Lane Cottage in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A picturesque lane plus a charming 2 bedroom, 2 full bath conch cottage set the scene for your best vacation ever. Wheth ...
From $201 per night (USD)
VRBO
From $989 per night (USD)
Expedia
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 $989 per night (USD)
Expedia
From $200 per night (USD)
VRBO
Peaceful and relaxing setting with the feel of the island!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
If Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort an ...
From $200 per night (USD)
VRBO
From $713 per night (USD)
Expedia
**TRUMAN’S TROVE @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Hunting for t ...
From $713 per night (USD)
Expedia
From $1013 per night (USD)
VRBO
Kemp House in Key West
Bedrooms:
4
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 $1013 per night (USD)
VRBO
From $375 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 $375 per night (USD)
Expedia
Click For Pricing
VRBO
5 Star Timeshare Resort - The Galleon located in Old Key West, Florida
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon, in the heart of "Old Town Key West" located on the historic Seaport/Marina and a short walk to world famous ...
Click For Pricing
VRBO
From $456 per night (USD)
Expedia
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn ...
From $456 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
$\Abaco\ Key West • 2\/2 End Unit Waterfront+Dockage$
From $652 per night (USD)
Expedia
\"Abaco\" Key West • 2\/2 End Unit Waterfront+Dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax & fish! Bring your family & friends to this 1350 sqft Waterfront corner home. Boat slips availabl ...
From $652 per night (USD)
Expedia
From $158 per night (USD)
VRBO
The Oasis: Stylishly Updated 1BR Home Convenient to Duval St & Beaches, Shared Pool & Pet-Friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additi ...
From $158 per night (USD)
VRBO
$Ashe St Serenade: 3BD\/3.5BA Luxury Retreat, Private Pool in an Island Oasis.$
From $416 per night (USD)
Expedia
Ashe St Serenade: 3BD\/3.5BA Luxury Retreat, Private Pool in an Island Oasis.
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Welcome to your dream getaway in the charming Old Town Key West, where the tranquility of island living meets the excite ...
From $416 per night (USD)
Expedia
From $338 per night (USD)
VRBO
**PERFECT HARMONY @ MIDTOWN** 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! PERFECT HARMO ...
From $338 per night (USD)
VRBO
$Lavender on White - 3 BD \/2 BA House w\/ Private Heated Pool and great Kitchen$
From $620 per night (USD)
Expedia
Lavender on White - 3 BD \/2 BA House w\/ Private Heated Pool and great Kitchen
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Nestled in a prime location, Lavender on White offers the perfect blend of tranquility and accessibility. Situated in th ...
From $620 per night (USD)
Expedia
$Priced to Book! 1BR\/1BA Walking distance to Duval St.$
Click For Pricing
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 ...
Click For Pricing
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 $534 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 $534 per night (USD)
VRBO
From $894 per night (USD)
Expedia
SEAPORT SAILING-Beach-Pool-King-BBQ-Hot Tub-Race Week!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
OCEANFRONT CASUAL LUXURY MARINA PENTHOUSE CONDO RENTAL WITH BREATHTAKING VIEWS OF KEY WEST HARBOR AND THE GULF OF MEXICO ...
From $894 per night (USD)
Expedia
From $200 per night (USD)
VRBO
Blue Heron by AvantStay | Pool & BBQ in Key West
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.* Welcome to our charm ...
From $200 per night (USD)
VRBO
$The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars$
From $494 per night (USD)
Expedia
The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars
Bedrooms:
3
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 $494 per night (USD)
Expedia
From $636 per night (USD)
VRBO
4-bedroom vacation home in Key West - steps to Duval St & Florida Keys Beaches
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
Escape to the heart of Key West's historic district and immerse yourself in the vibrant island lifestyle. This 4-bedroom ...
From $636 per night (USD)
VRBO
From $248 per night (USD)
Expedia
Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Keys Please Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $248 per night (USD)
Expedia
Click For Pricing
VRBO
Single home with pool, center of Old Town
Bedrooms:
1
Bathrooms:
3
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 ...
Click For Pricing
VRBO
$Three Condos w\/ Entertainment, Private Parking & Beach Nearby - Great for Groups$
From $1221 per night (USD)
Expedia
Three Condos w\/ Entertainment, Private Parking & Beach Nearby - Great for Groups
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Three Flowers Guesthouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $1221 per night (USD)
Expedia
From $388 per night (USD)
VRBO
Hollinsed House Studio - Great Location!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to Harvey's Haven—a beautiful studio in the heart of Old Town Key West! Conveniently located at the Hollinsed Ho ...
From $388 per night (USD)
VRBO
From $468 per night (USD)
VRBO
Traditional Two Queen, Pier House, Comfortable Ambiance, next to Nightlife Sight
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $468 per night (USD)
VRBO
From $295 per night (USD)
VRBO
LA CASITA EN CIMA~ Enjoy Key West in this lovely gem with a heated pool.
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 $295 per night (USD)
VRBO
From $356 per night (USD)
Expedia
**THE WICKED TUNA @ THE SEAPORT** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Get ready to ...
From $356 per night (USD)
Expedia
From $414 per night (USD)
VRBO
**CASA AVILA @ OLD TOWN** Private Home & 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! CASA AVILA co ...
From $414 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Cozy 2-bedroom cottage in Old Town Key West, with shared pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This memorable cottage is the perfect home base for your trip to Key West. With 2 bedrooms, including 1 king bed and 1 q ...
From $416 per night (USD)
Expedia
From $562 per night (USD)
VRBO
THREE ARCHES IN PARADISE~ A Mediterranean marvel in a walkable location!
Bedrooms:
4
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 $562 per night (USD)
VRBO
$Hyatt resort 2-bdr 2 bath Duvale St in Key West with kitchen washer\/dryer pool$
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Expedia
Hyatt resort 2-bdr 2 bath Duvale St in Key West with kitchen washer\/dryer pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Discover the beauty of Key West from this 2-bedroom 2 bath resort. The spacious bedrooms feature a king and queen bed, p ...
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Expedia
$ALL INCLUSIVE! Snorkel\/Sail\/Spear Fish\/Fishing\/Fun\n$
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VRBO
ALL INCLUSIVE! Snorkel\/Sail\/Spear Fish\/Fishing\/Fun\n
Bedrooms:
2
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 $402 per night (USD)
Expedia
Snowbird-friendly oasis with private heated pool, lush yard, & ample parking
Bedrooms:
3
Bathrooms:
4
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)
Expedia
$Dog-friendly condo near beach with pool, grill, outdoor shower, W\/D, AC$
From $180 per night (USD)
VRBO
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 $180 per night (USD)
VRBO
From $934 per night (USD)
Expedia
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 $934 per night (USD)
Expedia
From $906 per night (USD)
VRBO
Dos Casas - 2 House Compound in Old Town Key West - A Monthly Rental
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discerning travelers for ...
From $906 per night (USD)
VRBO
From $679 per night (USD)
Expedia
**GRENN TURTLE COTTAGE @ THE ANNEX** Stunning Private Home + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! GREEN TURTLE ...
From $679 per night (USD)
Expedia
$First Mate's Escape | Historic Apartment Near Duval w\/ Pool!$
Click For Pricing
VRBO
First Mate's Escape | Historic Apartment Near Duval w\/ Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Step back in time and embrace the enchanting history of Key West with a stay at First Mate's Escape, a stunning loft apa ...
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VRBO
From $363 per night (USD)
Expedia
Welcome Matt's - Truman @ Duval | Ideal One-Bedroom Retreat
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Truman @ Duval Unit B | Ideal One-Bedroom Retreat for Couples Escape to a charming one-bedroom apartment in the heart o ...
From $363 per night (USD)
Expedia
From $776 per night (USD)
VRBO
Charming 4-bedroom house with pool - 10 MIN. WALK TO DUVAL STREET
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Welcome to 1015 Eaton Street, nestled in the heart of the Historic Seaport neighborhood. Renovated in 2024, this 4-bedro ...
From $776 per night (USD)
VRBO
$THE FLAGLER ROOM @ The Inn on Fleming ~ 1st Floor King Room w\/ Shared Pool!$
From $323 per night (USD)
Expedia
THE FLAGLER ROOM @ The Inn on Fleming ~ 1st Floor King Room w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $323 per night (USD)
Expedia
$THE WHITEHEAD ROOM @ The Inn on Fleming ~ 2nd Floor Queen w\/ Shared Pool!$
From $306 per night (USD)
VRBO
THE WHITEHEAD ROOM @ The Inn on Fleming ~ 2nd Floor Queen w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $306 per night (USD)
VRBO
Click For Pricing
Expedia
Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 6, Swimming Pool, Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Have I mentioned that this listing is for the Songwriter’s Festival in sunny Key West, FL? You will be staying at the Hy ...
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Expedia
$THE MALLORY SUITE @ the Inn on Fleming ~ 1st Floor King Suite w\/ Shared Pool!$
From $365 per night (USD)
VRBO
THE MALLORY SUITE @ the Inn on Fleming ~ 1st Floor King Suite w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $365 per night (USD)
VRBO
From $782 per night (USD)
Expedia
Waterfront Resort, Songwriter’s Fest, Old Town, Sleeps 4, Swimming Pool, Hot Tub
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Have I mentioned that this listing is for the Songwriter’s Festival in sunny Key West, FL? You will be staying at the Hy ...
From $782 per night (USD)
Expedia
$THE HEMINGWAY SUITE @ the Inn on Fleming ~ 2nd Floor King w\/ Shared Pool!$
From $315 per night (USD)
VRBO
THE HEMINGWAY SUITE @ the Inn on Fleming ~ 2nd Floor King w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $315 per night (USD)
VRBO
$THE CORNISH SUITE @ Inn on Fleming ~ 3rd Floor 2 Bedroom w\/Shared Pool!$
From $359 per night (USD)
Expedia
THE CORNISH SUITE @ Inn on Fleming ~ 3rd Floor 2 Bedroom w\/Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $359 per night (USD)
Expedia
$THE SIMONTON ROOM @ The Inn on Fleming ~ 1st Floor King Room w\/ Shared Pool!$
From $297 per night (USD)
VRBO
THE SIMONTON ROOM @ The Inn on Fleming ~ 1st Floor King Room w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming was once the residence of Board of Edu ...
From $297 per night (USD)
VRBO
$Villa La Isla- Luxury Vacation Rental 1\/2 block from Duval$
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Expedia
Villa La Isla- Luxury Vacation Rental 1\/2 block from Duval
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Villa la Isla is a brand new, professionally designed luxury residence located in the heart of Old Town Key West. Walkin ...
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Expedia
From $559 per night (USD)
VRBO
**SPIRIT OF KEY WEST @ OLD TOWN** Exquisite Home & Pool + LAST KEY SERVICES…
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SPIRIT OF KEY ...
From $559 per night (USD)
VRBO
From $424 per night (USD)
Expedia
Ann Street Gardens in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key ...
From $424 per night (USD)
Expedia
Click For Pricing
VRBO
Peaceful & Relaxing Key West Bungalow, Near Famous Duval Street, Shops
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Discover the charm of Old Town in our vibrant retreat, steps away from Duval's delights. Dive into history at Hemingway' ...
Click For Pricing
VRBO
$The Secret Garden - Quaint 2 Bedroom \/ 2 Bath Cottage with Shared Pool & Hot Tub$
From $308 per night (USD)
Expedia
The Secret Garden - Quaint 2 Bedroom \/ 2 Bath Cottage with Shared Pool & Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
THE SECRET GARDEN – Charming 2 Bedroom / 2 Bathroom Cottage located in the Center of Old Town - 4 Guests - 2 Spaciou ...
From $308 per night (USD)
Expedia
$Coming Soon July 1! The Jolly Rooster\nNew! 2BR\/2BA - Walk to Duval$
From $336 per night (USD)
VRBO
Coming Soon July 1! The Jolly Rooster\nNew! 2BR\/2BA - Walk to Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coming July 1! UNDER RENOVATION - From the owners of the Dancing Rooster, this newly renovated 2BR/2BA home sleeps 6 and ...
From $336 per night (USD)
VRBO
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Expedia
Charming condo in awesome Key West - great location!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Key West at this wonderful condo. With amenities like King Size Bed, Private Front Porch, Pr ...
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Expedia
From $1001 per night (USD)
VRBO
3 Bedroom Key West Home with 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 $1001 per night (USD)
VRBO
From $893 per night (USD)
Expedia
Sophisticated 5 Bedroom Home With Cocktail Pool. Three streets from Duval!
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
The Blue Pineapple Estate combines a sophisticated blend of cosmopolitan tropical style with a touch of nostalgia, seaml ...
From $893 per night (USD)
Expedia
From $777 per night (USD)
VRBO
OSPREY STUDIO @ The Colony-Sleeps up to 4
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Osprey—a beautiful studio in the heart of Old Town Key West! Perfectly located at the Colony on Olivia Street ...
From $777 per night (USD)
VRBO
From $319 per night (USD)
Expedia
CONCH EASY LIVING -1 block to Duval-Monthly rental
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Discover Conch Easy Livin' at this monthly vacation home in the heart of Old Town Key West! You'll get a real feel of th ...
From $319 per night (USD)
Expedia
From $375 per night (USD)
VRBO
KNOT A WORRY so close to Duval at this monthly rental
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Knot A Worry is a monthly vacation home in the heart of Old Town Key West! Just one block from famous Duval Street, you' ...
From $375 per night (USD)
VRBO
$Casa Loca - so close to Duval 3bd\/2ba private home$
From $1110 per night (USD)
Expedia
Casa Loca - so close to Duval 3bd\/2ba private home
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Casa Loca is perfect for guests who want to enjoy the finest that Key West has to offer! The perfect location, less than ...
From $1110 per night (USD)
Expedia
From $738 per night (USD)
VRBO
Paradise Awaits @ SOLEIL CHALET
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Your own private paradise awaits in this peaceful neighborhood just steps away from the buzz of Duval Street. “Soleil Ch ...
From $738 per night (USD)
VRBO
From $208 per night (USD)
Expedia
KEY LIME COTTAGE - an adorable Monthly rental
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Located on the edge of Old Town near the art district on White Street, Key Lime Cottage offers great accommodations for ...
From $208 per night (USD)
Expedia
From $952 per night (USD)
VRBO
Bella Grand Premier Estate Key West - 2 Blocks off Duval w Private Pool
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Inspired by romantic turn-of-the-century architecture, Bella Grand Premier Estate is a unique Old Town Key West estate w ...
From $952 per night (USD)
VRBO
From $984 per night (USD)
Expedia
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 $984 per night (USD)
Expedia
From $800 per night (USD)
VRBO
Key West Paradise Returns - Gorgeous 3br 3.5ba in the Meadows, Old Town Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
This gorgeous 3br/3.5ba home is very private with a pool and spa, outdoor grill, three ensuite baths, chef's kitchen wit ...
From $800 per night (USD)
VRBO
From $368 per night (USD)
VRBO
Limelight Cottage on Southard
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to your dream vacation rental at the Limelight Cottage in Old Town Key West! This stunning two-bedroom, one-bath ...
From $368 per night (USD)
VRBO

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