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 $480 per night (USD)
VRBO
Loft Villa Steps from Duval!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Looking for where to stay in Key West, Florida? Look no further! Our One Bedroom Loft Villa features a queen bed downsta ...
From $480 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Galleon Resort Efficiency in the old town
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size b ...
From $349 per night (USD)
Expedia
From $485 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 $485 per night (USD)
VRBO
From $244 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 $244 per night (USD)
Expedia
From $238 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 $238 per night (USD)
VRBO
From $419 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 $419 per night (USD)
Expedia
From $238 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 $238 per night (USD)
VRBO
From $438 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 $438 per night (USD)
Expedia
From $455 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 $455 per night (USD)
VRBO
From $275 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 $275 per night (USD)
Expedia
From $433 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 $433 per night (USD)
VRBO
From $424 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 $424 per night (USD)
Expedia
From $301 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 $301 per night (USD)
VRBO
From $405 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 $405 per night (USD)
Expedia
From $454 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 $454 per night (USD)
VRBO
From $455 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 $455 per night (USD)
Expedia
From $444 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 $444 per night (USD)
VRBO
From $452 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 $452 per night (USD)
Expedia
From $470 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 $470 per night (USD)
VRBO
From $460 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 $460 per night (USD)
Expedia
From $449 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 $449 per night (USD)
VRBO
From $276 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 $276 per night (USD)
Expedia
From $493 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 $493 per night (USD)
VRBO
From $453 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 $453 per night (USD)
Expedia
From $502 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 $502 per night (USD)
VRBO
From $479 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 $479 per night (USD)
Expedia
From $278 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 $278 per night (USD)
VRBO
From $367 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 $367 per night (USD)
Expedia
From $469 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 $469 per night (USD)
VRBO
From $419 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 $419 per night (USD)
Expedia
From $460 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 $460 per night (USD)
VRBO
From $450 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 $450 per night (USD)
Expedia
From $452 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 $452 per night (USD)
VRBO
From $278 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 $278 per night (USD)
Expedia
From $467 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 $467 per night (USD)
VRBO
From $284 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 $284 per night (USD)
Expedia
From $457 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 $457 per night (USD)
VRBO
From $486 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 $486 per night (USD)
Expedia
From $448 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 $448 per night (USD)
VRBO
From $453 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 $453 per night (USD)
Expedia
From $457 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 $457 per night (USD)
VRBO
From $457 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 $457 per night (USD)
Expedia
From $421 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 $421 per night (USD)
VRBO
From $611 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 $611 per night (USD)
Expedia
From $619 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 $619 per night (USD)
VRBO
From $577 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 $577 per night (USD)
Expedia
From $611 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 $611 per night (USD)
VRBO
From $596 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 $596 per night (USD)
Expedia
From $435 per night (USD)
VRBO
The Pinder House: Historic Charm w/ Pool, Steps from Duval St & the Seaport
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additi ...
From $435 per night (USD)
VRBO
From $1597 per night (USD)
Expedia
A Palm Tree Haven in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This lovely single-family, two-story luxury home is in the prestigious Truman Annex gated community on a very private cu ...
From $1597 per night (USD)
Expedia
Click For Pricing
VRBO
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
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 $534 per night (USD)
VRBO
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)
VRBO
From $1712 per night (USD)
Expedia
Conch House in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Quintessential Grand Key West Estate! The James J. Curtis House c. 1874 was acquired by the Navy in 1903 and the home b ...
From $1712 per night (USD)
Expedia
From $132 per night (USD)
VRBO
Cubana Casita in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cubana Casita is an easy-access ground floor condo with one bedroom and 1 baths. This special home's 'from the ground up ...
From $132 per night (USD)
VRBO
From $181 per night (USD)
Expedia
The Sea Glass Cottage in Historic Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Spend time in beautiful Key West and live like a local in a true Conch Home! The Sea Glass Cottage is perfect for group ...
From $181 per night (USD)
Expedia
From $238 per night (USD)
VRBO
Airy & Bright Home with Pool in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The perfect getaway for a long stay in Key West. A private pool and patio area lie behind a green gate on a quiet lane i ...
From $238 per night (USD)
VRBO
From $436 per night (USD)
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 $436 per night (USD)
Expedia
From $156 per night (USD)
VRBO
Adorable gated loft studio two blocks from Duval in Old Town - Location Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Sanctuary is tucked away on a quiet street just two blocks off Duval St. in Old Town Key West. This hidden gem is on ...
From $156 per night (USD)
VRBO
From $1117 per night (USD)
VRBO
Stunning Views at The Galleon Resort in Beautiful Key West! Charming 2 Bed!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Concierge Realty is proud to present luxury villas at The Galleon Resort! **Reservations are available in weekly (7 nig ...
From $1117 per night (USD)
VRBO
From $263 per night (USD)
VRBO
Ultimate Escape-2 bed 2 bath Old Town home, parking, open layout, Mid-century
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $263 per night (USD)
VRBO
From $1047 per night (USD)
Expedia
**THE GILDED PINEAPPLE @ THE SEAPORT** Gorgeous Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! THE GILDED PI ...
From $1047 per night (USD)
Expedia
From $649 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 $649 per night (USD)
VRBO
From $794 per night (USD)
Expedia
The Caroline Suite | 1 bed, 1 bath condo w/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover your perfect island escape at The Caroline Suite, a recently refreshed 1 bedroom, 1 bathroom nightly vacation r ...
From $794 per night (USD)
Expedia
From $525 per night (USD)
VRBO
The Cozy Little Cottage!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to The Cozy Little Cottage !!! A REAL ISLAND GATAWAY IN KEY WEST!!! Nested in the heart of Key West, The Cozy L ...
From $525 per night (USD)
VRBO
From $413 per night (USD)
Expedia
Beautiful Old Town 2 bedroom Cottage on a Private Lane
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Located in the heart of Key West's historic district on a quiet lane with parking directly in front of the private gated ...
From $413 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Winter Months Open Frogmore on Fleming in Downtown Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to your dream residence in the heart of Key West, Florida! Nestled in a prime location, this 2-bedroom apartment ...
From $426 per night (USD)
VRBO
From $1148 per night (USD)
Expedia
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 $1148 per night (USD)
Expedia
From $317 per night (USD)
VRBO
Old Town Key West Hideaway with Poolside Fun! Free Breakfast!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 200 sq. ft, equipped with complimentary toiletries, standard ...
From $317 per night (USD)
VRBO
From $297 per night (USD)
VRBO
Romantic Key West Lodge with Outdoor Pool & Free Breakfast! Stunning Amenities
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This listing is for a room within a hotel. ✦ Your room is 240 sq. ft, equipped with complimentary toiletries, standard ...
From $297 per night (USD)
VRBO
From $579 per night (USD)
VRBO
Heart of Key West: Unique Stay with Outdoor Pool Access, Free Breakfast!
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 $579 per night (USD)
VRBO
From $152 per night (USD)
Expedia
Large 1 bedroom condo in the historic area of Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy your Key West vacation in this spacious 623 square foot condo located on the second floor of this classical reviva ...
From $152 per night (USD)
Expedia
From $2930 per night (USD)
VRBO
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
NEW LISTINGS APRIL - 2024! Welcome to the Pagitt House built in 1933 and located on Elizabeth Street just steps to all ...
From $2930 per night (USD)
VRBO
From $495 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 $495 per night (USD)
VRBO
From $344 per night (USD)
VRBO
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 $344 per night (USD)
VRBO
From $396 per night (USD)
Expedia
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 $396 per night (USD)
Expedia
From $301 per night (USD)
VRBO
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 $301 per night (USD)
VRBO
From $923 per night (USD)
Expedia
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 $923 per night (USD)
Expedia
From $349 per night (USD)
VRBO
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)
VRBO
From $321 per night (USD)
Expedia
GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Shared Heated Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
CAPTIVATING CLASSIC REVIVAL CHARM... Built in 1894, the delightful Inn on Fleming is an 11 room boutique hotel that was ...
From $321 per night (USD)
Expedia
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VRBO
Charming studio in Key West -Close to Duval. Beautiful Pool area.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Tropical Key West welcomes you to a classic Florida studio condominium, offering a plush king-size bed, casual living ar ...
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VRBO
From $1451 per night (USD)
VRBO
Perfect for Families! 2BR Suite with Balconies, Onsite Pool, Private Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1451 per night (USD)
VRBO
From $1451 per night (USD)
VRBO
Sea Breeze 2 Bedroom Oceanfront Suite at The Pier House Resort & Spa
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1451 per night (USD)
VRBO
From $1527 per night (USD)
VRBO
Pet-friendly Accommodation with Balcony, Outdoor Pool, Private White Sand Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1527 per night (USD)
VRBO
From $1527 per night (USD)
VRBO
Havana Heights Two Bedroom Suite at The Pier House Resort & Spa
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1527 per night (USD)
VRBO
From $340 per night (USD)
Expedia
**CALUSA SUITE @ SEAPORT INN ** Historic w/ Community Pool + LAST KEY SERVICES..
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 $626 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 $626 per night (USD)
VRBO
From $1350 per night (USD)
Expedia
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)
Expedia
From $908 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 $908 per night (USD)
VRBO
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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 ...
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Expedia
From $251 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 $251 per night (USD)
VRBO
From $558 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 $558 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 $900 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 $900 per night (USD)
VRBO
From $612 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 $612 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 $538 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 $538 per night (USD)
VRBO
From $1206 per night (USD)
Expedia
ELIZABETH'S SECRET: 3/2 In Old Town Key West, with a Private pool and Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Elizabeth's Secret! You have found your secret! A very private and secluded tropical oasis awaits you behin ...
From $1206 per night (USD)
Expedia
From $336 per night (USD)
VRBO
The Conch Republic Cooler
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to The Conch Republic Cooler! Nestled in the heart of quiet downtown Key West on the tranquil One Way Street, th ...
From $336 per night (USD)
VRBO
From $1350 per night (USD)
Expedia
Escape to Luxe 2BR Hyatt Sunset Harbor Villa! Dec 21-26, 3-Night Min Stay
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your Key West Paradise at Hyatt Vacation Club at Sunset Harbor. All fees included! Discover an unforgettable escape in ...
From $1350 per night (USD)
Expedia

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Results: 782 Rentals