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 $1584 per night (USD)
VRBO
Stylish Suite w/ Oceanfront View, Pool, Spa, & Steps to Historic Newport
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1584 per night (USD)
VRBO
From $1152 per night (USD)
VRBO
Pet-Friendly Ocean View Stay! Pool, Spa, Historic Sights Nearby!
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 $1152 per night (USD)
VRBO
From $1590 per night (USD)
VRBO
Lux Gulf View Suite! Pool, Marina Access, Walk to Dining Spots & Museums!
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 $1590 per night (USD)
VRBO
From $1279 per night (USD)
VRBO
Charming 2BR Stay, Ella’s | Garden Retreat w/ Pool Access and Free Breakfast!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $1279 per night (USD)
VRBO
From $1157 per night (USD)
VRBO
~CONCH COTTAGES~ Enjoy your next island vacation with friends right here!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
THE PROPERTY: Enjoy your stay with us at the quaint ‘Conch Cottages’ property, which includes 3 separate rentable units: ...
From $1157 per night (USD)
VRBO
From $347 per night (USD)
Expedia
~ROBINSON CRUSOE COTTAGE~ Delight in island vibes in this home with a pool.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
THE PROPERTY: Enjoy your stay with us at Robinson Crusoe Cottage, part of the quaint Conch Cottages property, which incl ...
From $347 per night (USD)
Expedia
From $943 per night (USD)
VRBO
OLD TOWN: 4 EN SUITES, POOL, PRIVATE PARKING STEPS TO DUVAL
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Just a block and half from iconic Duval Street, this beautifully renovated home blends classic Conch style charm with mo ...
From $943 per night (USD)
VRBO
From $438 per night (USD)
Expedia
** FLIGHT OF THE FLAMINGO @ OLD TOWN ** Home & Private Pool + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! After landing ...
From $438 per night (USD)
Expedia
From $1350 per night (USD)
VRBO
Premier resort overlooking the Gulf. Walk to Mallory Square, restaurants, beach.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Imbibe the relaxed Key West lifestyle from a coveted location in the heart of Old Town. Perfectly situated on the wester ...
From $1350 per night (USD)
VRBO
Click For Pricing
Expedia
Check out Hemmingway's 1st residence in the heart of downtown Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Want to live in paradise on a beautiful island for a month? Check out Hemmingway's 1st residence in the heart of downtow ...
Click For Pricing
Expedia
From $252 per night (USD)
VRBO
Southard Quarter at Truman Annex | Walk to Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to one of the most sought-after neighborhoods in Key West—Truman Annex. This quiet, gated community is known for ...
From $252 per night (USD)
VRBO
From $614 per night (USD)
Expedia
Hyatt Sunset Harbor Key West 1 Bedroom
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Hyatt Residence Club Sunset Harbor has the best location in the heart of Key West’s famed Old Town. Walk to Mallory Squa ...
From $614 per night (USD)
Expedia
From $755 per night (USD)
VRBO
Hyatt Sunset Harbor Key West 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hyatt Residence Club Sunset Harbor has the best location in the heart of Key West’s famed Old Town. Walk to Mallory Squa ...
From $755 per night (USD)
VRBO
From $834 per night (USD)
VRBO
Hemingway Retreat Suite at Suite Dreams Inn
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1 king bedroom with en suite bath, 1 queen bedroom with en suite bath, Full Kitchen, Dining Room, Living Room with Comfo ...
From $834 per night (USD)
VRBO
From $564 per night (USD)
VRBO
Key West Sunset Suite at Suite Dreams Inn
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
1 Queen Bedroom, 1 California King Bedroom, 1 Bathroom, Full Kitchen with dishwasher, Living Room with Double Trundle S ...
From $564 per night (USD)
VRBO
From $1856 per night (USD)
Expedia
Hyatt Sunset Harbor Resort- 2 Bedroom Villa- Old Town Key West- Walk Everywhere
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a great OCEANFRONT villa with a large balcony to watch sunsets! Hyatt Sunset Harbor is perfectly located in down ...
From $1856 per night (USD)
Expedia
From $605 per night (USD)
VRBO
Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Island Dreaming – Your Luxury Key West Getaway Welcome to Paradise Discover the ultimate island retreat at Island Dream ...
From $605 per night (USD)
VRBO
From $1131 per night (USD)
Expedia
Conch Cove - 3br/3ba with private heated pool and private parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Conch Cove | Heated Pool & Prime Location! Conch Cove is your private oasis in Old Town Key West! This 3-bedroom, 3-bat ...
From $1131 per night (USD)
Expedia
Click For Pricing
VRBO
Charming 1-bedroom/1-bath apartment in historical home with pool in Key West, FL
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Your cozy getaway awaits in Key West at this amazing apartment. Nestled in a beautiful private historical home in the he ...
Click For Pricing
VRBO
From $336 per night (USD)
Expedia
~SUNNY DAZE COTTAGE~ A private, newly constructed home in best location.
Bedrooms:
2
Bathrooms:
2
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 $336 per night (USD)
Expedia
From $258 per night (USD)
VRBO
SUNNY OUTLOOK~2 BR/2Ba 2nd FL, Waterfront views, Pool Access & Dockage!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This home is currently listed for sale and has been priced to offset showings that may be requested during your stay. ...
From $258 per night (USD)
VRBO
From $291 per night (USD)
Expedia
Charming pet friendly 2 bed/2 bath cottage 3 blocks from Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Consider this cottage your home away from home while you visit Key West. This pet friendly property features 2 bedrooms ...
From $291 per night (USD)
Expedia
Click For Pricing
VRBO
Magnificent views of the Gulf, Sunset Harbor is the ultimate island retreat.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled in Key West, this delightful resort offers 2 bedrooms with a king and queen bed, 2 bathrooms with luxurious amen ...
Click For Pricing
VRBO
From $662 per night (USD)
Expedia
BELLE MAISON ~ 5 BR/3 Ba Home w/ Pool/Spa in The Meadows!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
A LEGACY OF TIMELESS BEAUTY... This exquisite grand dame of quintessential Key West is a world of dreams! Yours is comin ...
From $662 per night (USD)
Expedia
From $386 per night (USD)
VRBO
Pet Friendly / Hot Tub / Close to Everything
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Located in Historic Old Town Monthly Rental La Cala is Situated on a Corner Lot within Walking Distance to Everything yo ...
From $386 per night (USD)
VRBO
From $294 per night (USD)
Expedia
**CALUSA SUITE @ SEAPORT INN ** Historic Charm & Community Pool + LAST KEY SERVI
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Want to be in ...
From $294 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Heron Hideaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to our unique and charming VRBO in Key West, located just a short distance from downtown. This cozy retreat off ...
From $362 per night (USD)
VRBO
From $251 per night (USD)
Expedia
**BARBUDA SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES..
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Looking for a ...
From $251 per night (USD)
Expedia
From $185 per night (USD)
VRBO
**MATECUMBE SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If you’d like ...
From $185 per night (USD)
VRBO
From $218 per night (USD)
Expedia
**ANTIGUA SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES..
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If the allure ...
From $218 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Cozy home with private pool, BBQ, central AC, enclosed yard
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Key to Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $469 per night (USD)
VRBO
From $1565 per night (USD)
Expedia
SEVENTH HEAVEN~Waterfront 5 BR, 4 Ba Townhome with Pool, Elevator & Dockage!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
OLD KEY WEST ELEGANCE WITH AN ELEVATOR, PRIVATE POOL AND BOAT DOCKAGE... Indulge in island chic as you approach this lux ...
From $1565 per night (USD)
Expedia
Click For Pricing
VRBO
Large Penthouse suite in the charming Bayan Resort in beautiful Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Banyan Resort Key West, Florida In the heart of historic Old Town Key West, The Banyan Resort boasts a storied hist ...
Click For Pricing
VRBO
From $285 per night (USD)
Expedia
**KOKOMO SUITE @ SEAPORT INN** Historic Charm & Community Pool + LAST KEY SERVIC
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! You can skip ...
From $285 per night (USD)
Expedia
From $325 per night (USD)
VRBO
ISLAND IN THE SUN ~ Newly Renovated 3 BR Townhome in Old Town with Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
EXCEPTIONAL SANCTUARY IN OLD TOWN... Lose yourself in this light and airy upscale retreat in a prime location, just 1.5 ...
From $325 per night (USD)
VRBO
From $574 per night (USD)
VRBO
Partial Harbor View King Room at Marker Key West Harbor Resort – Pet-friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $574 per night (USD)
VRBO
From $721 per night (USD)
VRBO
Harbor View King w/ Balcony at Marker Harbor Resort – Your Waterfront Oasis
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $721 per night (USD)
VRBO
From $372 per night (USD)
VRBO
Marker Key West Harbor, Classic Queen Room, 3 Swimming Pools & Pet-friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $372 per night (USD)
VRBO
From $721 per night (USD)
VRBO
Relax by the Water with Stunning Pools and Access to Watersports Activities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $721 per night (USD)
VRBO
From $574 per night (USD)
VRBO
Waterfront Living with Private Pools, Calm Waters, and Poolside Dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $574 per night (USD)
VRBO
From $776 per night (USD)
VRBO
Marker Key West Harbor, 2 Classic 2 Queens, 3 Onsite Pools & Pets are Welcome
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $776 per night (USD)
VRBO
From $392 per night (USD)
VRBO
Classic 2 Queen Room at Marker Key West Harbor - Minutes from the Ocean
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $392 per night (USD)
VRBO
From $416 per night (USD)
VRBO
Pool & Garden View 2 Queen Room at Marker Key West Harbor - Pet-friendly!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $416 per night (USD)
VRBO
From $372 per night (USD)
VRBO
Perfect Key West Hideaway with 3 Pools, Poolside Dining, and a Peaceful Setting
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $372 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Marker Key West Harbor, Pool & Garden View Room, 3 Outdoor Swimming Pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $428 per night (USD)
VRBO
From $392 per night (USD)
VRBO
Island Hideaway with Three Pools and Easy Access to Watersports Rentals
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $392 per night (USD)
VRBO
From $1204 per night (USD)
VRBO
3 Classic 2 Queen Rooms at Marker Key West Harbor - Pet-friendly Property
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms. ✦ Each room is ...
From $1204 per night (USD)
VRBO
From $362 per night (USD)
VRBO
Tranquil Island Getaway with Three Pools, Resort Dining, and Watersports
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $362 per night (USD)
VRBO
From $362 per night (USD)
VRBO
Classic King Room at Marker Key West Harbor - 3 Onsite Pools & Pet-Friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $362 per night (USD)
VRBO
From $417 per night (USD)
VRBO
Perfect Getaway with Pools, Relaxing Atmosphere, and Resort Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $417 per night (USD)
VRBO
From $1204 per night (USD)
VRBO
Relaxing Key West Getaway with 3 Onsite Swimming Pools, Minutes to Beaches
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms. ✦ Each room is ...
From $1204 per night (USD)
VRBO
From $832 per night (USD)
VRBO
2 Queen Rooms at Marker Key West Harbor - 3 Onsite Pools & Pet-friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $832 per night (USD)
VRBO
From $832 per night (USD)
VRBO
Relaxing Key West Retreat with Resort Pool, Minutes to Beaches & Attractions
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $832 per night (USD)
VRBO
From $776 per night (USD)
VRBO
Tropical Key West Retreat with 3 Swimming Pools, Steps from Dining & Shops
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $776 per night (USD)
VRBO
From $416 per night (USD)
VRBO
Escape to Paradise with Relaxing Pools and Watersports Right at Your Door
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This listing is for a room within a hotel. ✦ Your room is 400 sq. ft, equipped with complimentary toiletries, high defi ...
From $416 per night (USD)
VRBO
From $191 per night (USD)
Expedia
PATHWAY TO PARADISE ~ 2 BR/2.5 Ba Townhome w/ Shared Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
SHINY NEW ACCOMMODATION… This newly constructed townhome checks all the boxes for must-haves on your picture perfect Key ...
From $191 per night (USD)
Expedia
From $269 per night (USD)
VRBO
**SOUTHARD PEARL @ OLD TOWN** Condo & Community Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Among the man ...
From $269 per night (USD)
VRBO
From $235 per night (USD)
Expedia
Hyatt Sunset Harbor 1-bedroom suite w/AC, WiFi, Pool, Walk to Duval & Mallory
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience Key West in this enchanting 1-bedroom sleep4 suite with kitchen, living area with a queen sofa bed. Perfect f ...
From $235 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Sunshine State at Custom House Inn | Bright Studio on Duval Street!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Sunshine State at Custom House Inn | Bright Studio on Duval Street! Welcome to Sunshine State, your vibrant Key West es ...
From $362 per night (USD)
VRBO
From $498 per night (USD)
Expedia
Two Vibrant Suites on Duval - Custom House Inn
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Feather Queen at Custom House Inn: A Key West Gem on Duval Street Located in the vibrant heart of Duval Street, Feather ...
From $498 per night (USD)
Expedia
From $2385 per night (USD)
VRBO
Custom House Inn | 8 BR Suite Compound on Duval!
Bedrooms:
8
Bathrooms:
8
Sleeps:
25
Custom House Inn | Colorful Suites & Rooftop Vibes on Duval Street! Experience the ultimate group getaway at Custom Hou ...
From $2385 per night (USD)
VRBO
From $500 per night (USD)
Expedia
Two Modern Suites on Duval - Custom House Inn
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Chicken Water Cabana at Custom House Inn Located in the heart of vibrant Duval Street, Chicken Water Cabana at Custom H ...
From $500 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Underwater Cabana at Custom House Inn | Right In The Heart, On Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Underwater Cabana at Custom House Inn | Stay on Duval Street! Experience the heart of Key West with a stay at the Under ...
From $314 per night (USD)
VRBO
From $313 per night (USD)
Expedia
Birds of a Feather at Custom House Inn | Perfect Spot On Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Birds of a Feather at Custom House Inn | Vibrant Stay on Duval Street! Discover the heart of Key West at Birds of a Fea ...
From $313 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Chicken Run at Custom House Inn | Unbeatable Location On Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Chicken Run at Custom House Inn | Stay on Duval Street! Welcome to Chicken Run, a vibrant and uniquely themed studio lo ...
From $314 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Citrus Queen at Custom House Inn | Ideal Location On Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Citrus Queen at Custom House Inn | On Duval St! | Bright & Modern Studio Welcome to Citrus Queen, your vibrant, modern ...
From $314 per night (USD)
Expedia
From $614 per night (USD)
VRBO
Penthouse Near Downtown - The Maloney
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Woven throughout this 2,000+ square foot luxury penthouse is a story that can only be revealed by experience. ...
From $614 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Shared Pool & Parking - The Cottage at James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: Escape to this cozy 1-bedroom, 1-bathroom cottage nestled at the historic Curry Mansion Inn, right in the heart ...
From $349 per night (USD)
Expedia
From $230 per night (USD)
VRBO
THE GATO ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & 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 $230 per night (USD)
VRBO
From $281 per night (USD)
Expedia
GEIGER SUITE @ Inn on Fleming~ADULTS ONLY 2 BR 3rd Floor Suite 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 $281 per night (USD)
Expedia
From $227 per night (USD)
VRBO
THE TRUMAN ROOM @ Inn on Fleming ~ ADULTS ONLY 2nd Floor Queen & 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 $227 per night (USD)
VRBO
From $532 per night (USD)
Expedia
Southern Escape at Truman Annex - 2 Bed / 2.5 Bath with Parking & Shared Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
WELCOME to Southern Escape! Located in the Truman Annex Foundry building. This newly remodeled 2-bedroom, 2.5-bathroo ...
From $532 per night (USD)
Expedia
From $959 per night (USD)
VRBO
Pool, Laundry, and grilling area
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Upscale historic cigar barons mansion in walking distance to everything you desire in Key West. 3 spacious 1Br’s with o ...
From $959 per night (USD)
VRBO
From $421 per night (USD)
Expedia
New Listing! Truman Show - Private, heated pool and chef's kitchen
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Truman Show combines a rich history, a modern renovation and a desirable Old Town location. This beautiful home is con ...
From $421 per night (USD)
Expedia
From $808 per night (USD)
VRBO
Sailfish Suite on Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to the Sailfish Suite, your tropical retreat located in the heart of Key West! Situated on lively Duval Street, ...
From $808 per night (USD)
VRBO
From $2180 per night (USD)
VRBO
2 Hyatt Sunset Harbor Resort, In Town, Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This stylish place is close to must-see destinations. Discover this relaxing oasis in the heart of Key West's famed Old ...
From $2180 per night (USD)
VRBO
$\Dominica\ Key West 2BR • Dock, Pool, Pet-Friendly$
From $685 per night (USD)
VRBO
\"Dominica\" Key West 2BR • Dock, Pool, Pet-Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Relax in this 1,200 sq. ft. waterfront home in historic Downtown Key West! Walk or bike less than 1 mile to Duv ...
From $685 per night (USD)
VRBO
From $373 per night (USD)
VRBO
This cottage is a 1 bedroom(s), 1 bathrooms, located in Key West, FL.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to 734 Passover Lane, a charming one-bedroom cottage nestled in the heart of Key West’s historic district. This ...
From $373 per night (USD)
VRBO
From $597 per night (USD)
VRBO
Coral Palms Spacious 1BR Condo, King, Queen, Sofa Bed, Pool, Block to Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to this charming 1BR, 2nd-floor condo in the heart of Historic Key West. Sleep soundly in a plush king bed with r ...
From $597 per night (USD)
VRBO
From $804 per night (USD)
VRBO
Waterfront Condo with FREE Slip & Pool 2B/2B in Key West with AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Your Key West Paradise on Garrison Bight Marina! Escape to our charming Key West condo, where relaxation and ...
From $804 per night (USD)
VRBO
From $311 per night (USD)
VRBO
Charming two floor 1-bedroom bed & breakfast in fantastic Key West with AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Key West is waiting for you at this 1-bedroom bed & breakfast. A brilliant king bed awaits guests in this peaceful retre ...
From $311 per night (USD)
VRBO
From $206 per night (USD)
VRBO
Rooftop Renaissance - Upscale Condo in Old Town Key West. Perfect for Couples.
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Rooftop Renaissance vacation rental falls into a distinctive design category of Heritage Victorian - Meets Modern Luxury ...
From $206 per night (USD)
VRBO
From $169 per night (USD)
VRBO
Apartment in the heart of downtown Key West 1 block off Duval with private pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Want to live in paradise for a month? A one-bedroom large apartment downtown in the heart of Key West, one block off Duv ...
From $169 per night (USD)
VRBO
From $281 per night (USD)
VRBO
The Ivy Cottage - Private Home in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Tucked away on a quiet street in the heart of Old Town Key West you will find the quaint and comfortable Ivy Cottage. Th ...
From $281 per night (USD)
VRBO
From $495 per night (USD)
VRBO
The Meadows Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Your Island Escape Awaits – Tropical Luxury in the Heart of Key West Welcome to your dream getaway in the Florida Keys— ...
From $495 per night (USD)
VRBO
From $282 per night (USD)
VRBO
Windsor Blue Your Island Hideaway in the Heart of Old Town Key West with a Private Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Windsor Blue— Your Island Hideaway in the Heart of Old Town Key West Tucked away on charming Windsor Lane an ...
From $282 per night (USD)
VRBO
From $141 per night (USD)
VRBO
Apartment in historical hotel/home downtown Key West, one block off Duval St.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A beautiful loft style apartment in a historical hotel/home in the heart of Key West awaits you! There is an 8ft deep pr ...
From $141 per night (USD)
VRBO
From $1012 per night (USD)
VRBO
Fantastic Location, Old Town Waterfront Galleon Resort+Amenities, 2-Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 !! Our Galleon Resort accommodations in Historic Old Town-Key West, Florida – Where ...
From $1012 per night (USD)
VRBO
From $872 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 $872 per night (USD)
VRBO
From $3804 per night (USD)
VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy the glamour of this stylish, upscale place. Overlooking the shimmering span of Gulf of Mexico in historic Old Tow ...
From $3804 per night (USD)
VRBO
From $627 per night (USD)
VRBO
FLEMING-O (Flamingo) Cottage is the perfect getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Fleming-O (pronounced “flamingo”) is located on one-way Fleming Street in the middle of historic Old Town Key West and o ...
From $627 per night (USD)
VRBO
From $875 per night (USD)
VRBO
Modern Elegance at Windsor Townhomes #5
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
These beautiful villas boast over 1700 sq ft. on two levels for your vacation destination, with it’s own private garden ...
From $875 per night (USD)
VRBO
From $1410 per night (USD)
VRBO
CASA MARGARITA Steps to the Historic Seaport
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Casa Margarita is the ideal for outdoor dining, relaxing, and entertaining, with its spacious covered patio, ample seati ...
From $1410 per night (USD)
VRBO
From $582 per night (USD)
Expedia
Find your zen at HIDDEN TREASURE
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hidden from sight, among a colony of freestanding conch cottages and surrounded by lush tropical landscaping, you will f ...
From $582 per night (USD)
Expedia
From $359 per night (USD)
VRBO
Get your ISLAND STLYE on!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This quaint property offers resort-style accommodations at an affordable price! Nestled among a colony of freestanding C ...
From $359 per night (USD)
VRBO
From $507 per night (USD)
Expedia
HIDDEN OASIS 3 blocks from Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Tucked among a colony of freestanding Conch style cottages and lush tropical landscaping sits the newly renovated Hidden ...
From $507 per night (USD)
Expedia
From $1688 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 $1688 per night (USD)
VRBO
From $215 per night (USD)
Expedia
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 $215 per night (USD)
Expedia
From $705 per night (USD)
VRBO
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)
VRBO
From $2590 per night (USD)
Expedia
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 $2590 per night (USD)
Expedia

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