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 $1996 per night (USD)
VRBO
Key West Suites Hotel - Adam Scott Rote Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central ...
From $1996 per night (USD)
VRBO
From $956 per night (USD)
VRBO
Rare Penthouse 2 bed/2bath additional King in loft
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Perfect vacation rental that allows you to enjoy breakfast on your private balcony, unwind and relax in the master bath ...
From $956 per night (USD)
VRBO
From $771 per night (USD)
VRBO
The Galleon Resort in Beautiful Key West. Amazing Views! 2 bedroom villa!
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 $1147 per night (USD)
Expedia
JUNE-SEPT. WEEKLY DISCOUNT!!! - BOTTOMS UP BUNGALOW 2 Bed/2 Bath PRIVATE POOL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Bottom’s Up Bungalow located The Meadows subdivision in Old Town Key West. A true guest favorite with over 1 ...
From $1147 per night (USD)
Expedia
From $769 per night (USD)
VRBO
Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $769 per night (USD)
VRBO
From $664 per night (USD)
Expedia
BEACH HOUSE ~ Stunning 4B/4Ba Home with Private Pool in Truman Annex!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $664 per night (USD)
Expedia
From $253 per night (USD)
VRBO
Poolside Studio Villa Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Poolside Studio Villa is a stand-alone Key West vacation rental that features full kitchen appliances and a sitting ...
From $253 per night (USD)
VRBO
From $316 per night (USD)
Expedia
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 $316 per night (USD)
Expedia
From $298 per night (USD)
VRBO
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 $298 per night (USD)
VRBO
From $374 per night (USD)
Expedia
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 $374 per night (USD)
Expedia
From $239 per night (USD)
VRBO
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 $239 per night (USD)
VRBO
From $235 per night (USD)
Expedia
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 $235 per night (USD)
Expedia
From $238 per night (USD)
VRBO
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 $238 per night (USD)
VRBO
From $235 per night (USD)
Expedia
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 $235 per night (USD)
Expedia
From $244 per night (USD)
VRBO
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 $244 per night (USD)
VRBO
From $230 per night (USD)
Expedia
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 $230 per night (USD)
Expedia
From $231 per night (USD)
VRBO
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 $231 per night (USD)
VRBO
From $234 per night (USD)
Expedia
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 $234 per night (USD)
Expedia
From $230 per night (USD)
VRBO
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 $230 per night (USD)
VRBO
From $245 per night (USD)
Expedia
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 $245 per night (USD)
Expedia
From $234 per night (USD)
VRBO
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 $234 per night (USD)
VRBO
From $282 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 $282 per night (USD)
Expedia
From $288 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 $288 per night (USD)
VRBO
From $288 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 $288 per night (USD)
Expedia
From $291 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 $291 per night (USD)
VRBO
From $291 per night (USD)
Expedia
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 $291 per night (USD)
Expedia
From $284 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 $284 per night (USD)
VRBO
From $288 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 $288 per night (USD)
Expedia
From $282 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 $282 per night (USD)
VRBO
From $291 per night (USD)
Expedia
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 $291 per night (USD)
Expedia
From $291 per night (USD)
VRBO
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 $291 per night (USD)
VRBO
From $291 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 $291 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 $284 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 $284 per night (USD)
Expedia
From $265 per night (USD)
VRBO
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 $265 per night (USD)
VRBO
From $284 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 $284 per night (USD)
Expedia
From $265 per night (USD)
VRBO
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 $265 per night (USD)
VRBO
From $282 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 $282 per night (USD)
Expedia
From $282 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 $282 per night (USD)
VRBO
From $291 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 $291 per night (USD)
Expedia
From $284 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 $284 per night (USD)
VRBO
From $282 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 $282 per night (USD)
Expedia
From $291 per night (USD)
VRBO
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 $291 per night (USD)
VRBO
From $291 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 $291 per night (USD)
Expedia
From $291 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 $291 per night (USD)
VRBO
From $291 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 $291 per night (USD)
Expedia
From $291 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 $291 per night (USD)
VRBO
From $291 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 $291 per night (USD)
Expedia
From $282 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 $282 per night (USD)
VRBO
From $335 per night (USD)
Expedia
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 $335 per night (USD)
Expedia
From $297 per night (USD)
VRBO
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 $297 per night (USD)
VRBO
From $297 per night (USD)
Expedia
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 $297 per night (USD)
Expedia
From $303 per night (USD)
VRBO
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 $303 per night (USD)
VRBO
From $303 per night (USD)
Expedia
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 $303 per night (USD)
Expedia
From $302 per night (USD)
VRBO
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 $302 per night (USD)
VRBO
From $93 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 $93 per night (USD)
VRBO
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 $270 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 $270 per night (USD)
Expedia
From $215 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 $215 per night (USD)
VRBO
From $327 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 $327 per night (USD)
Expedia
From $1578 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 $1578 per night (USD)
VRBO
From $165 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 $165 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 $590 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 $590 per night (USD)
Expedia
From $1334 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 $1334 per night (USD)
VRBO
From $379 per night (USD)
Expedia
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 $379 per night (USD)
Expedia
Click For Pricing
VRBO
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
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
Click For Pricing
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 ...
Click For Pricing
VRBO
From $497 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 $497 per night (USD)
Expedia
From $324 per night (USD)
VRBO
Old Town Key West Hideaway with Poolside Fun! Free Breakfast!
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 $324 per night (USD)
VRBO
From $324 per night (USD)
VRBO
Romantic Key West Lodge with Outdoor Pool & Free Breakfast! 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 $324 per night (USD)
VRBO
From $390 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 $390 per night (USD)
VRBO
From $202 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 $202 per night (USD)
Expedia
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 $1018 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 $1018 per night (USD)
Expedia
From $310 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 $310 per night (USD)
VRBO
From $360 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 $360 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 $392 per night (USD)
Expedia
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)
Expedia
From $373 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 $373 per night (USD)
VRBO
From $438 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 $438 per night (USD)
Expedia
From $331 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 $331 per night (USD)
VRBO
From $980 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 $980 per night (USD)
Expedia
From $493 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 $493 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $1907 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 $1907 per night (USD)
VRBO
From $1907 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 $1907 per night (USD)
VRBO
From $1927 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 $1927 per night (USD)
VRBO
From $1927 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 $1927 per night (USD)
VRBO
From $580 per night (USD)
VRBO
Historic Key West Hideaway – Walk to the Seaport! Outdoor Pool, 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 $580 per night (USD)
VRBO
From $4667 per night (USD)
Expedia
Luxe two 4BDR/4BA Suites
Bedrooms:
8
Bathrooms:
8
Sleeps:
20
Welcome to Old Harbor House, an exquisite vacation rental combining two spacious 4-bedroom suites in the heart of Key We ...
From $4667 per night (USD)
Expedia
From $755 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 $755 per night (USD)
VRBO
From $1152 per night (USD)
VRBO
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 $1152 per night (USD)
VRBO
From $1590 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 $1590 per night (USD)
VRBO
From $558 per night (USD)
VRBO
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 $558 per night (USD)
VRBO
From $558 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 $558 per night (USD)
VRBO
From $1584 per night (USD)
VRBO
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 $1584 per night (USD)
VRBO
From $431 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 $431 per night (USD)
VRBO
From $431 per night (USD)
VRBO
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 $431 per night (USD)
VRBO

Search Your Destination Now!

Fleming Key Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 780 Rentals