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 $3017 per night (USD)
VRBO
Key West Room Retreat | Two Family Ready Suites Perfect For Long Stays
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3017 per night (USD)
VRBO
$Perfect Location to Key West Action! Pool and Garden View Room w\/ Balcony$
From $931 per night (USD)
VRBO
Perfect Location to Key West Action! Pool and Garden View Room w\/ Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $931 per night (USD)
VRBO
$Tropical Escape! 2 Spacious Rooms w\/ Balcony$
From $1822 per night (USD)
VRBO
Tropical Escape! 2 Spacious Rooms w\/ Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1822 per night (USD)
VRBO
$Relaxing Room w\/ Balcony & Breathtaking View$
From $986 per night (USD)
VRBO
Relaxing Room w\/ Balcony & Breathtaking View
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $986 per night (USD)
VRBO
$Spacious Suite w\/ Terrace & Scenic Harbor View$
From $1479 per night (USD)
VRBO
Spacious Suite w\/ Terrace & Scenic Harbor View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1479 per night (USD)
VRBO
From $1396 per night (USD)
VRBO
Best Spot Near Duval Street Nightlife! Suite ScenicHarbor View and Terrace
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1396 per night (USD)
VRBO
From $1760 per night (USD)
VRBO
Your Waterfront Hideaway in the Heart of Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1760 per night (USD)
VRBO
$Breathtaking Waterfront Retreat | Spacious 1BR Suite w\/ Living Area$
From $1509 per night (USD)
VRBO
Breathtaking Waterfront Retreat | Spacious 1BR Suite w\/ Living Area
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1509 per night (USD)
VRBO
$Chic Waterfront Room | 1BR Suite w\/ Balcony | Outdoor Pools$
From $1666 per night (USD)
VRBO
Chic Waterfront Room | 1BR Suite w\/ Balcony | Outdoor Pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1666 per night (USD)
VRBO
$Harbor front Hideaway w\/ Pools & Seaside Dining | 1BR Spacious Suite$
From $1595 per night (USD)
VRBO
Harbor front Hideaway w\/ Pools & Seaside Dining | 1BR Spacious Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1595 per night (USD)
VRBO
From $6102 per night (USD)
VRBO
4 Family Ready Suites | Spacious and Near Duval Street Nightlife
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $6102 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $100 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 $100 per night (USD)
VRBO
From $899 per night (USD)
Expedia
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 $899 per night (USD)
Expedia
From $294 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 $294 per night (USD)
VRBO
From $862 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 $862 per night (USD)
Expedia
From $604 per night (USD)
VRBO
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 $604 per night (USD)
VRBO
$The Caroline Suite | 1 bed, 1 bath condo w\/shared pool$
From $406 per night (USD)
Expedia
The Caroline Suite | 1 bed, 1 bath condo w\/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Caroline Suite is in The Bayview House, a completely remodeled historic house built in 1928. The 4 units and shared ...
From $406 per night (USD)
Expedia
From $1928 per night (USD)
VRBO
Tropical Hideaway: Room in Resort - Steps from Key West's Vibrance | 2 Units
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1928 per night (USD)
VRBO
From $291 per night (USD)
VRBO
Topsail Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Topsail Cottage XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX ...
From $291 per night (USD)
VRBO
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VRBO
The Pinder House: Discover Key West Charm at Historic Eyebrow Home, Steps from Duval St & Seaport!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additi ...
Click For Pricing
VRBO
$Waterfront Resort w\/ Outdoor Pools | Spacious Room w\/ Scenic View$
From $1022 per night (USD)
VRBO
Waterfront Resort w\/ Outdoor Pools | Spacious Room w\/ Scenic View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1022 per night (USD)
VRBO
$Scenic Old Town Key West Retreat w\/ Pool Access$
From $911 per night (USD)
VRBO
Scenic Old Town Key West Retreat w\/ Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $911 per night (USD)
VRBO
$Waterfront Stay in Duval St. Room w\/ Pool Access$
From $922 per night (USD)
VRBO
Waterfront Stay in Duval St. Room w\/ Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $922 per night (USD)
VRBO
$Escape to Key West w\/ Exclusive Waterfront Stay & Pool Access | 4 Family Rooms$
From $3857 per night (USD)
VRBO
Escape to Key West w\/ Exclusive Waterfront Stay & Pool Access | 4 Family Rooms
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3857 per night (USD)
VRBO
From $919 per night (USD)
VRBO
Tropical Getaway! Refreshing Pools: 2 Blocks Away from Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $919 per night (USD)
VRBO
From $973 per night (USD)
VRBO
Romantic Key West Getaway | Scenic Pool View Room
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $973 per night (USD)
VRBO
From $1258 per night (USD)
VRBO
Harbor Oasis Room: Tranquil Seaport & Water Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1258 per night (USD)
VRBO
From $1188 per night (USD)
VRBO
Perfect Key West Escape! Scenic Harbor View Room Ideal for Romantic Stay
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1188 per night (USD)
VRBO
$Relaxing Room w\/ Water View | Pool Access$
From $1081 per night (USD)
VRBO
Relaxing Room w\/ Water View | Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1081 per night (USD)
VRBO
From $1225 per night (USD)
VRBO
A Palm Tree Haven in Key West
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
This lovely single-family, two-story luxury home is in the prestigious Truman Annex gated community on a very private cu ...
From $1225 per night (USD)
VRBO
$Priced to book! 2 Bdr\/2Ba Walking distance to Duval St., Mallory Square, Trolley$
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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 ...
Click For Pricing
Expedia
From $1557 per night (USD)
VRBO
Conch House in Key West
Bedrooms:
4
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 $1557 per night (USD)
VRBO
From $127 per night (USD)
Expedia
Cubana Casita in Key West
Bedrooms:
2
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 $127 per night (USD)
Expedia
From $178 per night (USD)
VRBO
The Sea Glass Cottage in Historic Key West
Bedrooms:
2
Bathrooms:
3
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 $178 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 $219 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 $219 per night (USD)
VRBO
From $419 per night (USD)
Expedia
~ASHE HOUSE~ Renovated and relaxing with pool, porches, and privacy!
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 $419 per night (USD)
Expedia
From $307 per night (USD)
VRBO
Old Town Key West Hideaway with Poolside Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $307 per night (USD)
VRBO
From $307 per night (USD)
Expedia
Romantic Key West Lodge with Outdoor Pool & Stunning Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $307 per night (USD)
Expedia
From $385 per night (USD)
VRBO
Heart of Key West: Unique Stay with Outdoor Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $385 per night (USD)
VRBO
From $130 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 $130 per night (USD)
Expedia
$PAGITT HOUSE - 3\/ 2 - OLD TOWN KEY WEST WITH POOL$
From $2980 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 $2980 per night (USD)
VRBO
From $363 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 $363 per night (USD)
Expedia
From $328 per night (USD)
VRBO
Beautiful Old Town 2 bedroom Cottage on a Private Lane
Bedrooms:
2
Bathrooms:
3
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 $328 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Spend your Holidays at 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)
Expedia
$NEW listing!! Luxurious Island Pearl, 2 Bed\/2 Bath Home near Duval - Pool$
From $1229 per night (USD)
VRBO
NEW listing!! Luxurious Island Pearl, 2 Bed\/2 Bath Home near Duval - Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Looking for the perfect spot to soak up some sunshine and unwind in Key West? You’ve found it. Island Pearls is a stylis ...
From $1229 per night (USD)
VRBO
From $478 per night (USD)
Expedia
4-bedroom New Construction house with private pool in Key West
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Experience Island Living In The Treetops… Welcome to your luxurious oasis in Key West, where modern comfort meets tropic ...
From $478 per night (USD)
Expedia
From $628 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 $628 per night (USD)
VRBO
$Conch Cove - 3br\/3ba with private heated pool and private parking$
From $1469 per night (USD)
Expedia
Conch Cove - 3br\/3ba with private heated pool and private parking
Bedrooms:
3
Bathrooms:
4
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 $1469 per night (USD)
Expedia
$Charming 1-bedroom\/1-bath apartment in historical home with pool in Key West, FL$
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 $273 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 $273 per night (USD)
Expedia
$ISLAND DREAMIN' ~ Exceptional 4 BR\/3.5 Ba Home w\/ Pool!$
From $542 per night (USD)
VRBO
ISLAND DREAMIN' ~ Exceptional 4 BR\/3.5 Ba Home w\/ Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
MODERN MEETS CLASSIC KEY WEST STYLE... Located on the perfect corner of White and Petronia Streets, this understated bea ...
From $542 per night (USD)
VRBO
From $335 per night (USD)
Expedia
African Queen | Perfect Suite Near Historic Seaport, Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to African Queen Cottage, a charming retreat within the serene Harbor Walk Hideaways complex in Key West's Histo ...
From $335 per night (USD)
Expedia
From $394 per night (USD)
VRBO
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval! Shared Pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Atocha Cottage at Harbor Walk Hideaways Welcome to Atocha Cottage, a serene getaway nestled within the charming Harbor ...
From $394 per night (USD)
VRBO
$Pilar Cottage | Spectacular Studio w\/ Shared Pool$
From $343 per night (USD)
Expedia
Pilar Cottage | Spectacular Studio w\/ Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Pilar Cottage, a charming studio located within the peaceful Harbor Walk Hideaways complex in Key West's Hist ...
From $343 per night (USD)
Expedia
From $1165 per night (USD)
VRBO
Harbor Walk Hideaways | Group Compound In Old Town!
Bedrooms:
3
Bathrooms:
7
Sleeps:
14
Welcome to Harborwalk Hideaways! Overview: Discover Harbor Walk Hideaways, a beautifully renovated vacation rental comp ...
From $1165 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Sunshine State at Custom House Inn | Bright Studio on Duval Street!
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Sunshine State at Custom House Inn | Bright Studio on Duval Street! Welcome to Sunshine State, your vibrant Key West es ...
From $541 per night (USD)
Expedia
From $900 per night (USD)
VRBO
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 $900 per night (USD)
VRBO
From $4006 per night (USD)
Expedia
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 $4006 per night (USD)
Expedia
From $900 per night (USD)
VRBO
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 $900 per night (USD)
VRBO
From $486 per night (USD)
Expedia
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 $486 per night (USD)
Expedia
From $486 per night (USD)
VRBO
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 $486 per night (USD)
VRBO
From $486 per night (USD)
Expedia
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 $486 per night (USD)
Expedia
From $486 per night (USD)
VRBO
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 $486 per night (USD)
VRBO
From $513 per night (USD)
Expedia
Penthouse Near Downtown - The Maloney
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Woven throughout this 2,000+ square foot luxury penthouse is a story that can only be revealed by experience. ...
From $513 per night (USD)
Expedia
From $360 per night (USD)
VRBO
Shared Pool & Parking - The Cottage at James House
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Summary: Escape to this cozy 1-bedroom, 1-bathroom cottage nestled at the historic Curry Mansion Inn, right in the heart ...
From $360 per night (USD)
VRBO
$THE GATO ROOM @ The Inn on Fleming ~ 2nd Floor Queen Room w\/ Shared Pool!$
From $306 per night (USD)
Expedia
THE GATO ROOM @ The Inn on Fleming ~ 2nd Floor Queen 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 $306 per night (USD)
Expedia
$PATHWAY TO PARADISE ~ 2 BR\/2.5 Ba Townhome w\/ Shared Pool!$
From $215 per night (USD)
VRBO
PATHWAY TO PARADISE ~ 2 BR\/2.5 Ba Townhome w\/ Shared Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
SHINY NEW ACCOMMODATION… This newly constructed townhome checks all the boxes for must-haves on your picture perfect Key ...
From $215 per night (USD)
VRBO
From $269 per night (USD)
Expedia
**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)
Expedia
$THE GEIGER ROOM @ the Inn on Fleming ~ 3rd Floor 2 Bed Suite w\/ Shared Pool!$
From $371 per night (USD)
VRBO
THE GEIGER ROOM @ the Inn on Fleming ~ 3rd Floor 2 Bed 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 $371 per night (USD)
VRBO
$THE TRUMAN ROOM @ The Inn on Fleming ~ 2nd Floor Queen Room w\/ Shared Pool!$
From $353 per night (USD)
Expedia
THE TRUMAN ROOM @ The Inn on Fleming ~ 2nd Floor Queen 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 $353 per night (USD)
Expedia
$Southern Escape at Truman Annex - 2 Bed \/ 2.5 Bath with Parking & Shared Pool$
From $604 per night (USD)
VRBO
Southern Escape at Truman Annex - 2 Bed \/ 2.5 Bath with Parking & Shared Pool
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
WELCOME to Southern Escape! Located in the Truman Annex Foundry building. This newly remodeled 2-bedroom, 2.5-bathroo ...
From $604 per night (USD)
VRBO
From $981 per night (USD)
Expedia
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 $981 per night (USD)
Expedia
From $446 per night (USD)
VRBO
New Listing! Truman Show - Private, heated pool and chef's kitchen
Bedrooms:
4
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 $446 per night (USD)
VRBO
From $808 per night (USD)
Expedia
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)
Expedia
$Hyatt Sunset Harbor 1-bedroom suite w\/AC, WiFi, Pool, Walk to Duval & Mallory$
From $472 per night (USD)
VRBO
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 $472 per night (USD)
VRBO
From $340 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 $340 per night (USD)
Expedia
From $394 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 $394 per night (USD)
VRBO
From $499 per night (USD)
Expedia
Historic Key West Hideaway – Walk to the Seaport! Outdoor Pool, Pets Allowed!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $499 per night (USD)
Expedia
From $778 per night (USD)
VRBO
Passover Cottage | Private Pool & Ideal Key West Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Passover Cottage | Private Pool & Ideal Key West Location Passover Cottage is your ultimate retreat in the heart of Key ...
From $778 per night (USD)
VRBO
$SUNNY OUTLOOK~2 BR\/2Ba 2nd FL, Waterfront views, Pool Access & Dockage!$
From $254 per night (USD)
Expedia
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 $254 per night (USD)
Expedia
From $951 per night (USD)
VRBO
COME HIDE AT THE KEY WEST HOTEL. A HIDDEN WORLD RIGHT IN THE HEART OF IT ALL.
Bedrooms:
1
Bathrooms:
1
Sleeps:
50
(PLEASE REACH OUT TO GET ROOM DETAILA AND A SPECIAL DISCOUNT WHEN BOOKING!) Welcome to The Key West Hotel, tucked i ...
From $951 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Charming 2-bedroom 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 adorable property features 2 bedrooms with ...
From $402 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
$BELLE MAISON ~ 5 BR\/3 Ba Home w\/ Pool\/Spa in The Meadows!$
From $583 per night (USD)
Expedia
BELLE MAISON ~ 5 BR\/3 Ba Home w\/ Pool\/Spa in The Meadows!
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
A LEGACY OF TIMELESS BEAUTY... This exquisite grand dame of quintessential Key West is a world of dreams! Yours is comin ...
From $583 per night (USD)
Expedia
$Pet Friendly \/ Hot Tub \/ Close to Everything$
From $238 per night (USD)
VRBO
Pet Friendly \/ Hot Tub \/ Close to Everything
Bedrooms:
4
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 $238 per night (USD)
VRBO
From $1411 per night (USD)
Expedia
Newport Getaway! Pool, Spa, Onsite Dining, & Easy Access to Attractions!
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 $1411 per night (USD)
Expedia
From $1650 per night (USD)
VRBO
Pet-Friendly Stay, Pool, Spa, Fitness Center! 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 $1650 per night (USD)
VRBO
$Lux Waterfront Suite w\/ Pool, Spa, & Walk to Newport Marina & Attractions$
From $541 per night (USD)
Expedia
Lux Waterfront Suite w\/ Pool, Spa, & Walk to Newport Marina & Attractions
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $541 per night (USD)
Expedia
$Pet-Friendly Waterfront Escape w\/ Pool, Near Cliff Walk & Newport Fun$
From $679 per night (USD)
VRBO
Pet-Friendly Waterfront Escape w\/ Pool, Near Cliff Walk & Newport Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $679 per night (USD)
VRBO
From $1603 per night (USD)
Expedia
Spacious Oceanfront Stay! Spa, Fitness, & Steps to the Beach!
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 $1603 per night (USD)
Expedia
From $569 per night (USD)
VRBO
Chic Stay Near Newport Harbor & Cliff Walk! Pool, Spa, Fitness Center!
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 $569 per night (USD)
VRBO
From $716 per night (USD)
Expedia
Spacious Lanai Suite! Pool, Marina Access, Walk to Dining Spots & Museums
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 $716 per night (USD)
Expedia
$Stylish Suite w\/ Oceanfront View, Pool, Spa, & Steps to Historic Newport$
From $1505 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 $1505 per night (USD)
VRBO
From $1136 per night (USD)
Expedia
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 $1136 per night (USD)
Expedia
From $1284 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 $1284 per night (USD)
VRBO
$Charming 2BR Stay, Ella’s | Garden Retreat w\/ Pool Near Attractions & Eats$
From $1062 per night (USD)
Expedia
Charming 2BR Stay, Ella’s | Garden Retreat w\/ Pool Near Attractions & Eats
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 $1062 per night (USD)
Expedia
From $1222 per night (USD)
VRBO
~CONCH COTTAGES~ Enjoy your next island vacation with friends right here!
Bedrooms:
3
Bathrooms:
1
Sleeps:
8
THE PROPERTY: Enjoy your stay with us at the quaint ‘Conch Cottages’ property, which includes 3 separate rentable units: ...
From $1222 per night (USD)
VRBO
From $460 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 $460 per night (USD)
Expedia

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