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 $392 per night (USD)
VRBO
Washer & Dryer, Near Downtown - Mesa House, Uno
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Mesa House, Uno, is a charming condo in a prime location with a large front porch. Great for couples on a weeke ...
From $392 per night (USD)
VRBO
From $243 per night (USD)
Expedia
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
**This accommodation lies up a set of narrow, spiral stairs to a gorgeous room with dramatic, dormered ceilings within t ...
From $243 per night (USD)
Expedia
From $216 per night (USD)
VRBO
FUENTE ~ Adults Only, Spacious Poolview King Suite at Azul Mansion!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A DREAMY ESCAPE... Create your very own Key West story within the captivating, adults only Azul Queen Anne mansion which ...
From $216 per night (USD)
VRBO
From $199 per night (USD)
Expedia
CORONA ~ Adults Only, King Room with Community Pool at Azul Mansion!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ISLAND SANCTUARY... The grand and adults only Azul Queen Anne mansion awaits the creation of your tropical sabbatical wi ...
From $199 per night (USD)
Expedia
From $216 per night (USD)
VRBO
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
PERFECT RECIPE FOR RELAXATION... Make the most of your island sabbatical within the exquisite and adults only Azul Queen ...
From $216 per night (USD)
VRBO
From $240 per night (USD)
Expedia
CLARO ~ Adults Only, Pool View King Room in Azul Mansion!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A WORLD APART FROM REALITY... Indulge in this tropical retreat that possesses all the desirable amenities to make the mo ...
From $240 per night (USD)
Expedia
From $188 per night (USD)
VRBO
FONTANA ~ Adults Only, Pool Access King Room at Azul Mansion!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ISLAND SANCTUARY... Step up to the elegant, adults only Azul Queen Anne mansion for your dreamy island retreat. Built in ...
From $188 per night (USD)
VRBO
From $245 per night (USD)
Expedia
AMBROSIA ~ Adults Only, Poolside King Room in Azul Mansion!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
YOUR SOUTHERN SANCTUARY... Step foot inside the historic and adults only Azul Queen Anne mansion ready to capture your i ...
From $245 per night (USD)
Expedia
From $194 per night (USD)
VRBO
CORTEZ ~ Adults Only, Poolview King Room at Azul Mansion!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
FIND YOUR ZEN... The historic and charming Azul Queen Anne mansion sets the tone of your serene adults only retreat. Mar ...
From $194 per night (USD)
VRBO
From $199 per night (USD)
Expedia
HAVANA VIEJA ~ Adults Only, Poolside Queen Room w/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ELEGANT ISLAND RETREAT... Awaken your tropical senses in this incredible, adults only retreat located within the histori ...
From $199 per night (USD)
Expedia
From $242 per night (USD)
VRBO
FLOR DE CANA ~ Adults Only, Poolview Queen Room at Azul Mansion!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
YOUR SOUTHERN SANCTUARY... Conveniently residing in the historic Old Town district of Key West, the dreamy and adults on ...
From $242 per night (USD)
VRBO
From $222 per night (USD)
Expedia
CAPTIVA ~ Adults Only, King Room with Community Pool at Azul Mansion!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
RELAX, UNWIND & ESCAPE... Immerse yourself within the charming, adults only Azul Queen Anne mansion built in 1899 by shi ...
From $222 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Classic King, Pool - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $302 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Classic King & Private Balcony - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $306 per night (USD)
Expedia
From $310 per night (USD)
VRBO
Classic King & Private Balcony - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $310 per night (USD)
VRBO
From $313 per night (USD)
Expedia
Deluxe King, Pet Friendly & - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $313 per night (USD)
Expedia
From $290 per night (USD)
VRBO
King Bed + Sleeper Sofa & Balcony -James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $290 per night (USD)
VRBO
From $289 per night (USD)
Expedia
King Suite with Balcony - The James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $289 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Classic King & Private Balcony - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $303 per night (USD)
VRBO
From $281 per night (USD)
Expedia
Classic King, Pool - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $281 per night (USD)
Expedia
From $330 per night (USD)
VRBO
King Bed + Sleeper Sofa & Balcony -James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $330 per night (USD)
VRBO
From $292 per night (USD)
Expedia
King Suite + 2 Twins & Balcony – The James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $292 per night (USD)
Expedia
From $291 per night (USD)
VRBO
King Suite, Pet Friendly & Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $291 per night (USD)
VRBO
From $290 per night (USD)
Expedia
King Suite, Pet Friendly & Shared Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $290 per night (USD)
Expedia
From $282 per night (USD)
VRBO
King Suite with Balcony - The James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $282 per night (USD)
VRBO
From $271 per night (USD)
Expedia
Classic Queen, Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $271 per night (USD)
Expedia
From $293 per night (USD)
VRBO
King Suite with Balcony - The James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $293 per night (USD)
VRBO
From $264 per night (USD)
Expedia
Classic Queen, Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $264 per night (USD)
Expedia
From $299 per night (USD)
VRBO
Classic King, Pool - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $299 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Classic King, Pool - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $292 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Deluxe King, Pet Friendly & - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $315 per night (USD)
VRBO
From $288 per night (USD)
Expedia
King Suite with Balcony - The James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $288 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Classic King, Pool - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $298 per night (USD)
VRBO
From $293 per night (USD)
Expedia
King Suite + 2 Twins & Balcony – The James House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - The historic James House sits on Caroline street, just one home away from Duval street and its coveted attrac ...
From $293 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Deluxe Queen & Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $315 per night (USD)
VRBO
From $291 per night (USD)
Expedia
Classic King, Pool - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $291 per night (USD)
Expedia
From $417 per night (USD)
VRBO
Deluxe Queen & Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $417 per night (USD)
VRBO
From $310 per night (USD)
Expedia
Deluxe Queen & Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $310 per night (USD)
Expedia
From $311 per night (USD)
VRBO
Deluxe Queen & Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $311 per night (USD)
VRBO
From $309 per night (USD)
Expedia
Deluxe Queen & Pet Friendly - Curry Mansion Inn
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - Built in 1869, the iconic Curry Mansion features 21 unique guest rooms. - Located on Caroline Street, just ha ...
From $309 per night (USD)
Expedia
From $370 per night (USD)
VRBO
Studio Near Downtown - The Bartlum
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Welcome to the Bartlum, a historic and luxurious studio apartment just steps to Duval Street. This studio, lo ...
From $370 per night (USD)
VRBO
From $266 per night (USD)
Expedia
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Beautiful 1st floor queen room just off the pool for easy access... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ...
From $266 per night (USD)
Expedia
From $289 per night (USD)
VRBO
NumberEleven ~ Charming Adult Only, 1 Bedroom, 1 Bath w/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Charming 1st Floor King for Convenience... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-o ...
From $289 per night (USD)
VRBO
From $281 per night (USD)
Expedia
HONEY~ Adult Only, 2nd Floor 1 King Bedroom Unit w/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Gorgeous 2nd floor king room and ample balcony space... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of ...
From $281 per night (USD)
Expedia
From $325 per night (USD)
VRBO
KEITT ~ Adult Only, 2nd Floor 1 Bedroom w/ Shared Pool, Scarlet Mango Inn!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Bright and airy 2nd floor king room... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only ...
From $325 per night (USD)
VRBO
From $334 per night (USD)
Expedia
JULIE ~ Adult Only, 1st Floor King Bedroom w/ Shared Pool, Scarlet Mango Inn!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Lovely 1st floor king room steps from the pool for easy access... DELIGHT IN OLD WORLD ALLURE... Bask in the charming a ...
From $334 per night (USD)
Expedia
From $218 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 $218 per night (USD)
VRBO
From $385 per night (USD)
Expedia
~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 $385 per night (USD)
Expedia
Click For Pricing
VRBO
The Pinder House: Discover Key West Charm at Historic Eyebrow Home, Steps from Duval St & 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 ...
Click For Pricing
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $1573 per night (USD)
VRBO
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 $1573 per night (USD)
VRBO
From $130 per night (USD)
Expedia
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 $130 per night (USD)
Expedia
From $178 per night (USD)
VRBO
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 $178 per night (USD)
VRBO
From $95 per night (USD)
Expedia
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 $95 per night (USD)
Expedia
From $771 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 $771 per night (USD)
VRBO
From $292 per night (USD)
Expedia
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 $292 per night (USD)
Expedia
From $568 per night (USD)
VRBO
**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 $568 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 $1241 per night (USD)
VRBO
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 $1241 per night (USD)
VRBO
Click For Pricing
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 $396 per night (USD)
VRBO
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 $396 per night (USD)
VRBO
From $281 per night (USD)
Expedia
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 $281 per night (USD)
Expedia
From $285 per night (USD)
VRBO
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 $285 per night (USD)
VRBO
From $294 per night (USD)
Expedia
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 $294 per night (USD)
Expedia
From $784 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 $784 per night (USD)
VRBO
From $325 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 $325 per night (USD)
Expedia
From $308 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 $308 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
From $130 per night (USD)
VRBO
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)
VRBO
From $2980 per night (USD)
Expedia
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)
Expedia
From $478 per night (USD)
VRBO
4-bedroom New Construction house with private pool in Key West
Bedrooms:
4
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)
VRBO
From $916 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 $916 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 $278 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 $278 per night (USD)
Expedia
From $392 per night (USD)
VRBO
ISLAND DREAMIN' ~ Exceptional 4 BR/3.5 Ba Home w/ Pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
MODERN MEETS CLASSIC KEY WEST STYLE... Located on the perfect corner of White and Petronia Streets, this understated bea ...
From $392 per night (USD)
VRBO
From $259 per night (USD)
Expedia
African Queen | Perfect Suite Near Historic Seaport, Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to African Queen Cottage, a charming retreat within the serene Harbor Walk Hideaways complex in Key West's Histo ...
From $259 per night (USD)
Expedia
From $346 per night (USD)
VRBO
Atocha Cottage at Harbor Walk Hideaways | 2 Blocks From Duval! Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Atocha Cottage at Harbor Walk Hideaways Welcome to Atocha Cottage, a serene getaway nestled within the charming Harbor ...
From $346 per night (USD)
VRBO
From $244 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 $244 per night (USD)
Expedia
From $1064 per night (USD)
VRBO
Harbor Walk Hideaways | Group Compound In Old Town!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Welcome to Harborwalk Hideaways! Overview: Discover Harbor Walk Hideaways, a beautifully renovated vacation rental comp ...
From $1064 per night (USD)
VRBO
From $344 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 $344 per night (USD)
Expedia
From $192 per night (USD)
VRBO
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 $192 per night (USD)
VRBO
From $250 per night (USD)
Expedia
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 $250 per night (USD)
Expedia
From $407 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 $407 per night (USD)
VRBO
From $2828 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 $2828 per night (USD)
Expedia
From $553 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 $553 per night (USD)
VRBO
From $330 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 $330 per night (USD)
Expedia
From $347 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 $347 per night (USD)
VRBO
From $242 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 $242 per night (USD)
Expedia
From $329 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 $329 per night (USD)
VRBO
From $497 per night (USD)
Expedia
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 $497 per night (USD)
Expedia
From $191 per night (USD)
VRBO
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)
VRBO
From $260 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 $260 per night (USD)
Expedia
From $311 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 $311 per night (USD)
VRBO
From $175 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 $175 per night (USD)
Expedia
From $463 per night (USD)
VRBO
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 $463 per night (USD)
VRBO
From $883 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 $883 per night (USD)
Expedia
From $437 per night (USD)
VRBO
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 $437 per night (USD)
VRBO
From $591 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 $591 per night (USD)
Expedia
From $251 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 $251 per night (USD)
VRBO
From $472 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 $472 per night (USD)
Expedia

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Results: 758 Rentals