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 $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 $301 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 $301 per night (USD)
Expedia
From $405 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 $405 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 $1712 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 $1712 per night (USD)
VRBO
From $132 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 $132 per night (USD)
Expedia
From $181 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 $181 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 $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 $1047 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 $1047 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 $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 $2930 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 $2930 per night (USD)
Expedia
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 $622 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 $622 per night (USD)
Expedia
From $1189 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 $1189 per night (USD)
VRBO
From $4265 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 $4265 per night (USD)
Expedia
From $515 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 $515 per night (USD)
VRBO
From $305 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 $305 per night (USD)
Expedia
From $593 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 $593 per night (USD)
VRBO
From $626 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 $626 per night (USD)
Expedia
From $662 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 $662 per night (USD)
VRBO
From $744 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 $744 per night (USD)
Expedia
Click For Pricing
VRBO
Check out Hemmingway's 1st residence in the heart of downtown Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Want to live in paradise on a beautiful island for a month? Check out Hemmingway's 1st residence in the heart of downtow ...
Click For Pricing
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 $1432 per night (USD)
Expedia
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 $1432 per night (USD)
Expedia
From $1305 per night (USD)
VRBO
~CONCH COTTAGES~ Enjoy your next island vacation with friends right here!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
THE PROPERTY: Enjoy your stay with us at the quaint ‘Conch Cottages’ property, which includes 3 separate rentable units: ...
From $1305 per night (USD)
VRBO
From $329 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 $329 per night (USD)
Expedia
From $258 per night (USD)
VRBO
**SOUTHARD PEARL @ OLD TOWN** Condo & Community Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Among the man ...
From $258 per night (USD)
VRBO
From $758 per night (USD)
Expedia
Southern Escape at Truman Annex - 2 Bed / 2.5 Bath with Parking & Shared Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Southern Escape — Your Perfect Key West Getaway! Nestled in the heart of the Truman Annex Foundry building, ...
From $758 per night (USD)
Expedia
From $522 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 $522 per night (USD)
VRBO
From $1543 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 $1543 per night (USD)
Expedia
From $321 per night (USD)
VRBO
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)
VRBO
From $696 per night (USD)
Expedia
BELLE MAISON ~ 5 BR/3 Ba Home w/ Pool/Spa in The Meadows!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
A LEGACY OF TIMELESS BEAUTY... This exquisite grand dame of quintessential Key West is a world of dreams! Yours is comin ...
From $696 per night (USD)
Expedia
From $508 per night (USD)
VRBO
**BARBUDA SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES..
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Looking for a ...
From $508 per night (USD)
VRBO
From $194 per night (USD)
Expedia
**MATECUMBE SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If you’d like ...
From $194 per night (USD)
Expedia
From $239 per night (USD)
VRBO
**ANTIGUA SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES..
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If the allure ...
From $239 per night (USD)
VRBO
From $556 per night (USD)
Expedia
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 $556 per night (USD)
Expedia
From $1592 per night (USD)
VRBO
SEVENTH HEAVEN~Waterfront 5 BR, 4 Ba Townhome with Pool, Elevator & Dockage!
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
OLD KEY WEST ELEGANCE WITH AN ELEVATOR, PRIVATE POOL AND BOAT DOCKAGE... Indulge in island chic as you approach this lux ...
From $1592 per night (USD)
VRBO
Click For Pricing
Expedia
Large Penthouse suite in the charming Bayan Resort in beautiful Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Banyan Resort Key West, Florida In the heart of historic Old Town Key West, The Banyan Resort boasts a storied hist ...
Click For Pricing
Expedia
From $303 per night (USD)
VRBO
**KOKOMO SUITE @ SEAPORT INN** Historic Charm & Community Pool + LAST KEY SERVIC
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! You can skip ...
From $303 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 $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
From $584 per night (USD)
VRBO
THE WRITER'S COTTAGE ~ Renovated 2 BR/2 Ba Home w/ Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
NOSTALGIC AND INSPIRATIONAL HAVEN... History permeates and echoes through the classic Dade Pine details of this lovingly ...
From $584 per night (USD)
VRBO
From $1245 per night (USD)
Expedia
Luxe Designer Oasis + Guest House steps off Duval
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Discover unparalleled luxury at Autograph House, an exclusive private oasis just one block from the center of Key West. ...
From $1245 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Southernmost Seclusion, central to Old Town hot spots. Pool, balconies, parking
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
- Two private outdoor spaces – greet the sunrise on the covered balcony, toast the sunset on a second, tree‑top perch. ...
From $383 per night (USD)
VRBO
From $333 per night (USD)
Expedia
10% Off Adv Rate-Upgraded Cottage-Steps to Famous Duval Street &Historic Seaport
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Offering an additional 10% off current advertised rate on all bookings. Located in the historic district of Key West thi ...
From $333 per night (USD)
Expedia
From $642 per night (USD)
VRBO
AZURE KEY WEST - Stunning New Home with Heated Pool - 4 Bedrooms Available
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Unwind in Key West at this lovely villa. Completely renovated top-to-bottom and completed in 2025, with 4 bedrooms inclu ...
From $642 per night (USD)
VRBO
From $784 per night (USD)
Expedia
NEW LISTING 4 ENSUITE BEDROOMS , OLD TOWN, PARKING, AC, POOL, BLOCK FROM DUVAL
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Discover Key West at its finest from your private luxury retreat just a block and a half off Duval Street. Newly renova ...
From $784 per night (USD)
Expedia
From $830 per night (USD)
VRBO
**BOHEMIA @ OLD TOWN** Fully Renovated Home & Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Welcome to BO ...
From $830 per night (USD)
VRBO
From $569 per night (USD)
Expedia
Blanco Luxury Villa | 4 bedrooms & 4 baths in the heart of Old Town
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Blanco Luxury Villa, your dream getaway in the heart of Old Town Key West. Located near the waterfront in Ol ...
From $569 per night (USD)
Expedia
From $799 per night (USD)
VRBO
Old Town 3/3 Home, Private Pool, Off Street Parking, Outdoor Dining, Balconies
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to paradise in Old Town Key West! This spacious 3BR/3BA home features gorgeous hardwood floors, a huge dining ro ...
From $799 per night (USD)
VRBO
From $568 per night (USD)
VRBO
The Meadows Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Your Island Escape Awaits – Tropical Luxury in the Heart of Key West Welcome to your dream getaway in the Florida Keys— ...
From $568 per night (USD)
VRBO
$\Dominica\ Key West 2BR • Dock, Pool, Pet-Friendly$
From $731 per night (USD)
VRBO
\"Dominica\" Key West 2BR • Dock, Pool, Pet-Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Relax in this 1,200 sq. ft. waterfront home in historic Downtown Key West! Walk or bike less than 1 mile to Duv ...
From $731 per night (USD)
VRBO
From $894 per night (USD)
VRBO
SEAPORT PANORAMA-Beach-Pool-King-BBQ-Kitchen views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY V ...
From $894 per night (USD)
VRBO
From $154 per night (USD)
VRBO
The Ivy Cottage - Private Home in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Tucked away on a quiet street in the heart of Old Town Key West you will find the quaint and comfortable Ivy Cottage. Th ...
From $154 per night (USD)
VRBO
From $1579 per night (USD)
VRBO
Modern Elegance at Windsor Townhomes #5
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
These beautiful villas boast over 1700 sq ft. on two levels for your vacation destination, with it’s own private garden ...
From $1579 per night (USD)
VRBO
From $1510 per night (USD)
VRBO
CASA MARGARITA Steps to the Historic Seaport
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Casa Margarita is the ideal for outdoor dining, relaxing, and entertaining, with its spacious covered patio, ample seati ...
From $1510 per night (USD)
VRBO
From $823 per night (USD)
Expedia
Find your zen at HIDDEN TREASURE
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hidden from sight, among a colony of freestanding conch cottages and surrounded by lush tropical landscaping, you will f ...
From $823 per night (USD)
Expedia
From $772 per night (USD)
VRBO
Get your ISLAND STLYE on!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This quaint property offers resort-style accommodations at an affordable price! Nestled among a colony of freestanding C ...
From $772 per night (USD)
VRBO
From $651 per night (USD)
Expedia
HIDDEN OASIS 3 blocks from Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Tucked among a colony of freestanding Conch style cottages and lush tropical landscaping sits the newly renovated Hidden ...
From $651 per night (USD)
Expedia
From $1044 per night (USD)
VRBO
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 $1044 per night (USD)
VRBO
From $705 per night (USD)
Expedia
FERNWOOD ~ Dreamy, Lush Estate with Incredible Outdoor Space with Pool & Spa!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
THERE'S NO PLACE LIKE YOUR ISLAND HOME... Located in the highly sought-after area of The Meadows and beneath peaceful sw ...
From $705 per night (USD)
Expedia
From $3350 per night (USD)
VRBO
Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21
Bedrooms:
7
Bathrooms:
10
Sleeps:
21
The Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-s ...
From $3350 per night (USD)
VRBO
From $544 per night (USD)
Expedia
BRIGHT SUNSHINY DAY ~ Renovated 3 BR, 4 Ba Home w/ Pool, Spa & Exercise Room!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
OLD TOWN CLASSIC... This beautifully redesigned Conch house is in the heart of Key West. Located in the outstanding loc ...
From $544 per night (USD)
Expedia
From $411 per night (USD)
VRBO
THE WEEKEND HOUSE ~ 3 Bedroom, 2 Bath Condo Centrally Located w/ Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
WHERE LIFE IS PURE… This dreamy 3 bedroom, 2 bathroom island getaway is sure to captivate the true essence of Key West c ...
From $411 per night (USD)
VRBO
Click For Pricing
Expedia
The Sandy Beach House in Historic Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Spend time in Key West and live like a local in a true Conch Home! The Sandy Beach Cottage, a fully-renovated first floo ...
Click For Pricing
Expedia
From $282 per night (USD)
VRBO
UPTOWN FUNK ~ Newly Renovated 3 BR Townhome in Old Town with Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
IMMACULATE UPSCALE DELIGHT… Embrace the island vibes and immerse yourself in the Key West spirit in this enchanting 3 st ...
From $282 per night (USD)
VRBO
From $683 per night (USD)
VRBO
Ann Street Tranquility: A cozy and peaceful cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Stre ...
From $683 per night (USD)
VRBO
From $641 per night (USD)
VRBO
Deluxe Key West Ocean Front Condo Week - April 22 - 29, 2025
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Deluxe Ocean Front Condo in Key West Florida with a spectacular 3rd Floor balcony view of the Marina and Ocean. One Full ...
From $641 per night (USD)
VRBO
From $1751 per night (USD)
Expedia
Key West Suites Hotel #201 on Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Key West Suites Hotel #201 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it u ...
From $1751 per night (USD)
Expedia
From $534 per night (USD)
VRBO
Old Town Bali Hideaway For 2, Just Steps From Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Perfect for two, this Bali style, studio cottage has it all... COMFORT and LOCATION. Located on an Ann Street compound j ...
From $534 per night (USD)
VRBO
Click For Pricing
Expedia
Hyatt Sunset Harbor on the Water-Luxury Key West 2 Bedroom Condo Dec 21-Dec 28.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is the luxury boutique resort you and your family and friends deserve. A few steps to famous Mallory Square and all ...
Click For Pricing
Expedia
From $208 per night (USD)
VRBO
Private Home in Heart of Old Town (Shared Pool!)
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Come escape to paradise in this newly updated and available home steps from Duval! Equipped with all the amenities for a ...
From $208 per night (USD)
VRBO
From $516 per night (USD)
Expedia
Caroline On My Mind-New Listing-Light, Bright and Airy!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street offers a unique and inviting exp ...
From $516 per night (USD)
Expedia
From $267 per night (USD)
VRBO
Hidden Treasure in Old Town: 3BR Home with Pool in Peaceful Gated Enclave
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Your Key West Hideaway home is located in the heart of Old Town. Key West landmarks, attractions, Duval St, restaurants, ...
From $267 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Cottage in Old Town Key West w/ Pool, Parking and Privacy. One block from Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Down a hidden lane in the heart of Old Town Key West you will find Loco Court Cottages.The compound is located one block ...
From $293 per night (USD)
Expedia
From $679 per night (USD)
VRBO
**SOUTHERNMOST BLISS @ OLD TOWN** Newly Renovated Home & Pool + LAST KEY SERVICE
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SOUTHERNMOST ...
From $679 per night (USD)
VRBO
From $2921 per night (USD)
VRBO
CLASSIC KEY WEST - Grand home in Old Town location
Bedrooms:
7
Bathrooms:
7
Sleeps:
14
The Mansion, circa 1840’s is a lovingly restored and renovated three story Classic Folk Victorian home with seven bedroo ...
From $2921 per night (USD)
VRBO
From $1227 per night (USD)
VRBO
PERFECTION...STEPS FROM DUVAL ~
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
The Villa is a newer built poolside home, situated steps away from famous Duval Street, the historic seaport and everyth ...
From $1227 per night (USD)
VRBO
From $4150 per night (USD)
VRBO
WATSON HOUSE GRAND ESTATE on Simonton St
Bedrooms:
11
Bathrooms:
11
Sleeps:
22
The Grand Estate is comprised of the Mansion and the Villa offering 11 bedrooms and baths. It is ideal for family gather ...
From $4150 per night (USD)
VRBO
From $510 per night (USD)
VRBO
TROPICAL PROPERTIES VACATION RENTAL-KEY WEST
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
****This property requires a minimum stay of 28 nights in the same calendar month**** Tropical Properties Vacation Rent ...
From $510 per night (USD)
VRBO
From $930 per night (USD)
Expedia
**MODERN IN THE MEADOWS @ THE MEADOWS** Chic Private Home & Pool + LAST KEY SERV
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! MODERN IN THE ...
From $930 per night (USD)
Expedia
From $238 per night (USD)
VRBO
WINDSONG DELIGHT - Cute house on Windsor Ln
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This two story townhome has both location and amenities for a wonderful month long visit to Key West. Secluded at the r ...
From $238 per night (USD)
VRBO
From $218 per night (USD)
Expedia
Key Lime Pie by AvantStay | Ideal Location w/ Splash Pool & Out Door Dining
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Key Lime Pie is a private cottage that perfectly en ...
From $218 per night (USD)
Expedia
From $857 per night (USD)
VRBO
Old Town Key West Luxury 4BR – Private Pool by Historic Seaport - Monthly Rental
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Escape to the heart of Key West's historic district and immerse yourself in the vibrant island lifestyle. This 4-bedroom ...
From $857 per night (USD)
VRBO
$\A Bird's Eye View\ at The Truman Annex in Key West$
From $451 per night (USD)
Expedia
\"A Bird's Eye View\" at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Stunning, Modern 2 bedroom, 1 bathroom second floor condo in the Truman Annex Shipyard Complex completely renovated. Ful ...
From $451 per night (USD)
Expedia

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Results: 382 Rentals