Fleming Key Rentals
From $433 per night (USD)VRBO
Serene Bungalow with Outdoor Pool Access | Free Breakfast Onsite!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $433 per night (USD)VRBO
From $483 per night (USD)VRBO
Romantic Getaway with Plush Turkish Robes & Inviting Pools! Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $483 per night (USD)VRBO
From $461 per night (USD)VRBO
Key West Oasis: Retreat in Historical Bungalows with Pool, Free Breakfast!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $461 per night (USD)VRBO
From $482 per night (USD)VRBO
Serene Bungalow in Key West: Poolside Refreshers & Free Breakfast!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $482 per night (USD)VRBO
From $465 per night (USD)VRBO
Tranquil Bungalow w/ an Artistic Vibe in Vibrant Key West | Breakfast Included
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $465 per night (USD)VRBO
From $439 per night (USD)VRBO
Stylish Room in the Heart of Old Town w/ Access to Outdoor Pool | Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $439 per night (USD)VRBO
From $519 per night (USD)VRBO
Historical Charm in a Room Surrounded by Key West's Best: Free Breakfast!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $519 per night (USD)VRBO
From $393 per night (USD)VRBO
Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $393 per night (USD)VRBO
From $1148 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 $1148 per night (USD)VRBO
From $2427 per night (USD)VRBO
4 Traditional Two Queen, Pier House Resort, Island Elegance, Duval St. Access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2427 per night (USD)VRBO
From $713 per night (USD)VRBO
One Bedroom Suite Queens, Pier House, Roomy Elegance, Beachside Bliss, Key West
- 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 $713 per night (USD)VRBO
From $640 per night (USD)VRBO
Serene Resort Room with Private Beach & Spa - Perfect Key West Escape
- 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 $640 per night (USD)VRBO
From $989 per night (USD)VRBO
One Bedroom Suite King, Pier House, Spacious Comfort, Spa Access, Ocean Breeze
- 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 $989 per night (USD)VRBO
From $937 per night (USD)VRBO
Oceanfront King, Pier House, Stunning Ocean Views, Plush King Bed, Duval Locale
- 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 $937 per night (USD)VRBO
From $656 per night (USD)VRBO
Family-Friendly Key West Resort with Private Beach on Duval St.
- 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 $656 per night (USD)VRBO
From $950 per night (USD)VRBO
Inviting Key West Paradise Perfect for Couples - Spa & Oceanfront Views
- 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 $950 per night (USD)VRBO
From $713 per night (USD)VRBO
Relaxing Key West Haven with Full-Service Spa and Legendary Dining
- 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 $713 per night (USD)VRBO
From $640 per night (USD)VRBO
Lanai Two Queen, Pier House, Tropical Views, Beachfront Access, Key West Charm
- 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 $640 per night (USD)VRBO
From $1801 per night (USD)VRBO
3 Traditional Two Queen, Pier House Resort, Fine Dining, Near Mallory Square
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1801 per night (USD)VRBO
From $2780 per night (USD)VRBO
3 Charming Resort Stays with Private Beach & Spa Treatments - Key West Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2780 per night (USD)VRBO
From $1230 per night (USD)VRBO
2 Traditional Two Queen, Pier House Resort, Beachside, Key West Vibe
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1230 per night (USD)VRBO
From $939 per night (USD)VRBO
Oceanfront Two Queen, Pier House, Beach Panorama, Custom Decor, Pet-Friendly
- 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 $939 per night (USD)VRBO
From $1907 per night (USD)VRBO
2 Oceanfront Two Queen, Pier House Resort, Beach Access, Pet-Friendly, Duval St.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
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 $683 per night (USD)VRBO
Key West Beachfront Accommodation - Ideal for Family Vacation 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 $683 per night (USD)VRBO
From $1230 per night (USD)VRBO
2 Serene Beachside Accommodations with Enhanced Spa Experience in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1230 per night (USD)VRBO
From $1907 per night (USD)VRBO
2 Sophisticated Resort Rooms Perfect for Family Relaxation! Spa Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
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 $656 per night (USD)VRBO
Traditional King, Pier House, Classic Island Style, Fine Dining, Duval Street Proximity
- 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 $656 per night (USD)VRBO
From $678 per night (USD)VRBO
Pure Wellness Spa Junior Suite, Pier House, Private Beach Access, Duval St.
- 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 $678 per night (USD)VRBO
From $606 per night (USD)VRBO
Beachfront Bliss with Water Activities & Next to Vibrant Nightlife 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 $606 per night (USD)VRBO
From $939 per night (USD)VRBO
Unique Island-Style Rooms with Custom Furniture & Art in Key West
- 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 $939 per night (USD)VRBO
From $1051 per night (USD)VRBO
Pet-Friendly Coastal Retreat in Key West with Private Beach Access
- 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 $1051 per night (USD)VRBO
From $933 per night (USD)VRBO
Chic Beachfront Stays - Enjoy Ocean Views & Private Sand in Key West
- 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 $933 per night (USD)VRBO
From $2427 per night (USD)VRBO
4 Key West Stays with Spa, Private Beach & Culinary Delights - On Duval St.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2427 per night (USD)VRBO
From $2775 per night (USD)VRBO
3 Oceanfront Two Queen, Pier House Resort, Beachfront Leisure, Key West Sunset
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $2775 per night (USD)VRBO
From $1132 per night (USD)VRBO
Oceanfront Suite, Pier House, Serene Waterfront, Elegant Dining, Island Life
- 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 $1132 per night (USD)VRBO
From $1801 per night (USD)VRBO
3 Island-Chic Rooms Offering Private White Sand Beach on Duval St. in Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Dive into Key West's heart! Located on the lively Duval St., moments from Hemingway's home, and the iconic Southernmost ...
From $1801 per night (USD)VRBO
From $205 per night (USD)VRBO
Southard Retreat- 2 bed 2 bath townhome downtown w/ pool, parking
- 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 $205 per night (USD)VRBO
From $2058 per night (USD)VRBO
Galleon Resort, Pool, Hot Tub, In Town, Pool, Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort offers a multitude of accommodations in studio, one-bedroom and two-bedroom configurations. Studios h ...
From $2058 per night (USD)VRBO
From $1612 per night (USD)VRBO
Banyon Resort, Beach, Pool, Hot Tub, In Town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
In the heart of historic Old Town Key West, The Banyan Resort boasts a storied history and sits on a historic, mid-1800' ...
From $1612 per night (USD)VRBO
From $760 per night (USD)VRBO
Everything Key West has to offer @ Mango Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This historic Conch house is an excellent vacation home which has been thoughtfully remodeled to provide the best in mod ...
From $760 per night (USD)VRBO
From $710 per night (USD)VRBO
A Bit of Heaven is the perfect monthly rental in Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This quintessential Key West eyebrow home is located in Old Town's prime Historic District, sitting just blocks away fro ...
From $710 per night (USD)VRBO
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 $367 per night (USD)VRBO
The Hideout! Where Luxury Meets Location. Fully Renovated, with Pool.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to The Hideout, where luxury meets location. Look no further than "The Hideout" for upscale luxury and single- ...
From $367 per night (USD)VRBO
From $3646 per night (USD)VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy the glamour of this stylish, upscale place. Overlooking the shimmering span of Gulf of Mexico in historic Old Tow ...
From $3646 per night (USD)VRBO
From $1762 per night (USD)VRBO
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $1762 per night (USD)VRBO
From $769 per night (USD)VRBO
FLEMING-O (Flamingo) Cottage is the perfect getaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Fleming-O (pronounced “flamingo”) is located on one-way Fleming Street in the middle of historic Old Town Key West and o ...
From $769 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)VRBO
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)VRBO
From $772 per night (USD)Expedia
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)Expedia
From $651 per night (USD)VRBO
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)VRBO
From $415 per night (USD)Expedia
Hollinsed House Studio - Great Location!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Welcome to Harvey's Haven—a beautiful studio in the heart of Old Town Key West! Conveniently located at the Hollinsed Ho ...
From $415 per night (USD)Expedia
From $1425 per night (USD)VRBO
Spacious Townhome on Windsor Lane 3/3.5
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Windsor Townhomes #3! Once you enter this beautifully decorated oasis…your vacation begins. This townhome has ...
From $1425 per night (USD)VRBO
From $417 per night (USD)VRBO
KEY LIME COTTAGE - an adorable Monthly rental
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Located on the edge of Old Town near the art district on White Street, Key Lime Cottage offers great accommodations for ...
From $417 per night (USD)VRBO
From $649 per night (USD)VRBO
Paradise Awaits @ SOLEIL CHALET
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Your own private paradise awaits in this peaceful neighborhood just steps away from the buzz of Duval Street. “Soleil Ch ...
From $649 per night (USD)VRBO
From $1765 per night (USD)VRBO
Windsor Townhomes #6 - Large pool 3B/3.5 bath, 3 blocks to Duval
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a q ...
From $1765 per night (USD)VRBO
From $679 per night (USD)VRBO
CONCH EASY LIVING -1 block to Duval-Monthly rental
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Discover Conch Easy Livin' at this monthly vacation home in the heart of Old Town Key West! You'll get a real feel of th ...
From $679 per night (USD)VRBO
From $318 per night (USD)VRBO
KNOT A WORRY so close to Duval at this monthly rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Knot A Worry is a monthly vacation home in the heart of Old Town Key West! Just one block from famous Duval Street, you' ...
From $318 per night (USD)VRBO
From $1484 per night (USD)VRBO
Casa Loca - so close to Duval 3bd/2ba private home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Casa Loca is perfect for guests who want to enjoy the finest that Key West has to offer! The perfect location, less than ...
From $1484 per night (USD)VRBO
From $505 per night (USD)Expedia
OSPREY STUDIO @ The Colony-Sleeps up to 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Osprey—a beautiful studio in the heart of Old Town Key West! Perfectly located at the Colony on Olivia Street ...
From $505 per night (USD)Expedia
From $1053 per night (USD)VRBO
Relax in Style at Windsor Townhomes #4
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a q ...
From $1053 per night (USD)VRBO
From $606 per night (USD)VRBO
Traditional Two Queen, Pier House, Comfortable Ambiance, next to Nightlife Sight
- 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 $606 per night (USD)VRBO
From $413 per night (USD)VRBO
LA CASITA EN CIMA~ Enjoy Key West in this lovely gem with a heated pool.
- 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 $413 per night (USD)VRBO
From $837 per night (USD)Expedia
**THE WICKED TUNA @ THE SEAPORT** Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Get ready to ...
From $837 per night (USD)Expedia
From $557 per night (USD)VRBO
**CASA AVILA @ OLD TOWN** Private 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! CASA AVILA co ...
From $557 per night (USD)VRBO
From $403 per night (USD)Expedia
Boomerang Boathouse in Key West
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Richley individual yet classic Key West are phrases that echo from Boomerang Boathouse, a 4 bedroom, 2.5 bath home with ...
From $403 per night (USD)Expedia
From $949 per night (USD)VRBO
THREE ARCHES IN PARADISE~ A Mediterranean marvel in a walkable location!
- 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 $949 per night (USD)VRBO
From $600 per night (USD)Expedia
Pool, Pet Friendly, & Near Duval - Coastal Rose
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Experience the charm of downtown Key West in this cozy 1-bedroom unit with an additional loft and a shared pool ...
From $600 per night (USD)Expedia
From $529 per night (USD)VRBO
Pet Friendly, Near Duval - Rose Petal Petite Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Located in downtown Key West, the 'Rose Petal Petite Suite' offers a cozy and charming accommodation experience ...
From $529 per night (USD)VRBO
From $1039 per night (USD)Expedia
Pet Friendly, & Near Duval - Rose Key Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Escape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in s ...
From $1039 per night (USD)Expedia
From $368 per night (USD)VRBO
Casa Tranquila - Fully-Renovated 2-bedroom Townhome in Old Town Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Casa Tranquila! This 2-bedroom townhome is perfect for your escape to Key West. Located in Old Town just five ...
From $368 per night (USD)VRBO
From $972 per night (USD)VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $972 per night (USD)VRBO
From $700 per night (USD)VRBO
Stunning Key West Stay Perfect for a Romantic Escape! Pool, Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $700 per night (USD)VRBO
From $244 per night (USD)Expedia
Charming 2-bedroom House in Historic Key West with Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Embrace the Enchantment of Old Key West Charm! Escape to the enchanting world of Key West Hideaway, where history meets ...
From $244 per night (USD)Expedia
From $660 per night (USD)VRBO
Ann Street Gardens in Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key ...
From $660 per night (USD)VRBO
From $407 per night (USD)VRBO
Modern Lodge w/ Outdoor Pool Access & Free Breakfast, Near Attractions!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This listing is for a room within a hotel. ✦ Your room is 420 sq. ft, equipped with complimentary toiletries, standard ...
From $407 per night (USD)VRBO
From $804 per night (USD)VRBO
2 Rooms for the whole family w/ Pool Access & Free Breakfast, Near Museums!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms. ✦ Each room is ...
From $804 per night (USD)VRBO
From $651 per night (USD)VRBO
2 Bedroom Suite w/ Outdoor Pool in Old Town Key West! Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This listing is for a room within a hotel. ✦ Your room is 800 sq. ft, equipped with complimentary toiletries, kitchen w ...
From $651 per night (USD)VRBO
From $4065 per night (USD)VRBO
Pool & Parking, & Near Duval - The Rigby House
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Escape to paradise with this stunning 6-bedroom, 6.5 bathroom home nestled in the heart of historic Key West. W ...
From $4065 per night (USD)VRBO
From $3331 per night (USD)VRBO
Spacious 5-bdrm 5 bathroom house in charming Key West with AC, WiFi, Plunge Pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Short walk to Duval Street. Central location. Restaurants nearby. Surrounded by charm of Key West. Explore the city the ...
From $3331 per night (USD)VRBO
Click For PricingVRBO
Hyatt resort 2-bdr 2 bath Duvale St in Key West with kitchen washer/dryer pool
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the beauty of Key West from this 2-bedroom 2 bath resort. The spacious bedrooms feature a king and queen bed, p ...
Click For PricingVRBO
From $166 per night (USD)Expedia
Chic 1BR w/ Balcony in Old Town – Walk to Duval!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Galveston Porches – Stylish One-Bedroom in the Heart of Old Town Key West Welcome to Galveston Porches, your perfect ho ...
From $166 per night (USD)Expedia
From $1125 per night (USD)VRBO
Charming Bungalow Perfect for Families! Free Breakfast and Pool Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $1125 per night (USD)VRBO
From $348 per night (USD)Expedia
Discover this cozy retreat in the charm of Old Town Key West at Poorhouse Lane!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3-bedroom house is perfect for your escape to Key West. This cozy retreat offers prime location near all the action ...
From $348 per night (USD)Expedia
From $575 per night (USD)VRBO
**SOUTHERN STAR @ THE MEADOWS** Private Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SOUTHERN STAR ...
From $575 per night (USD)VRBO
From $117 per night (USD)Expedia
Serene Key West Studio with Poolside Peace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio Apartment for Rent in Key West This cozy studio apartment is located in a quiet, gated community on Grinnell Str ...
From $117 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 $932 per night (USD)Expedia
Coco's Poolside Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Coco’s Poolside Retreat is a cheerful three-story townhome tucked inside a private, gated mini-compound in Old Town Key ...
From $932 per night (USD)Expedia
From $1711 per night (USD)VRBO
The Flower Power House - Boho Beautiful
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 13
When you enter the gate next to the painted 1306 sign, you’ll find yourself immersed in this one-of-a-kind tropical wond ...
From $1711 per night (USD)VRBO
From $2439 per night (USD)VRBO
2 Hyatt Sunset Harbor Resort, In Town, Marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This stylish place is close to must-see destinations. Discover this relaxing oasis in the heart of Key West's famed Old ...
From $2439 per night (USD)VRBO
From $1543 per night (USD)VRBO
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)VRBO
From $146 per night (USD)Expedia
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 ...
From $146 per night (USD)Expedia
From $423 per night (USD)VRBO
Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Palm Isle! A tropical 2nd-floor condo in the charming Meadows area of Key West. Relax on your private front ...
From $423 per night (USD)VRBO
From $286 per night (USD)Expedia
Gypsyginny's Hideaway in downtown Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Set in the heart of Key West's vibrant Meadows district, this delightful 3-bedroom vacation rental on iconic White Stree ...
From $286 per night (USD)Expedia
From $2026 per night (USD)VRBO
Meadows Manor | Elegant Oasis with Private Pool & Parking!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Meadows Manor | Elegant Oasis with Private Pool & Parking --- 3-Night Minimum Stay Required --- Discover the perfect b ...
From $2026 per night (USD)VRBO
From $344 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 $344 per night (USD)Expedia
From $396 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 $396 per night (USD)VRBO
From $301 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 $301 per night (USD)Expedia