Fleming Key Rentals
From $1144 per night (USD)VRBO
Waterfront Getaway | 2 Spacious Family Rooms w\/ Balcony | Old Town Best
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1144 per night (USD)VRBO
From $422 per night (USD)VRBO
Bohemian Retreat with Pool in Old Town Key West | Walk to Duval Street
- 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 $422 per night (USD)VRBO
From $679 per night (USD)VRBO
Romantic Key West Getaway with Heated Pool, Patio & 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 $679 per night (USD)VRBO
From $453 per night (USD)VRBO
Quaint Bungalow w\/ Private Outdoor Space Near Duval Street | 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 $453 per night (USD)VRBO
From $573 per night (USD)VRBO
Celebrate History in Key West: Tropical Bungalow Retreat Ideal for Relaxation
- 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 $573 per night (USD)VRBO
From $529 per night (USD)VRBO
Spacious Bungalow with Patio | Near Ernest Hemingway Home – 7 Min Walk
- 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 $529 per night (USD)VRBO
From $513 per night (USD)VRBO
Serene Bungalow with Outdoor Pool Access | Near Historic Ernest Hemingway Museum
- 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 $513 per night (USD)VRBO
From $465 per night (USD)VRBO
Romantic Getaway with Plush Turkish Robes & Inviting Pools Near Duval Street
- 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 $465 per night (USD)VRBO
From $714 per night (USD)VRBO
Key West Oasis: Retreat in Historical Bungalows with Pool Paradise
- 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 $714 per night (USD)VRBO
From $673 per night (USD)VRBO
Tropical Escape: Artistic-Vibe Bungalows with Balcony | Welcome Drinks Included
- 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 $673 per night (USD)VRBO
From $597 per night (USD)VRBO
Enchanting Hideaway Perfect for Couples Seeking Romantic Bliss
- 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 $597 per night (USD)VRBO
From $457 per night (USD)VRBO
Serene Bungalow in Key West: Poolside Refreshers & Relaxing Amenities
- 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 $457 per night (USD)VRBO
From $621 per night (USD)VRBO
Couples' Retreat: Romantic Unit with Patio | Delicious Breakfast Included
- 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 $621 per night (USD)VRBO
From $695 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 $695 per night (USD)VRBO
From $463 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 $463 per night (USD)VRBO
From $543 per night (USD)VRBO
Historical Charm in a Room Surrounded by Key West's Best: Complimentary Breakfas
- 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 $543 per night (USD)VRBO
From $635 per night (USD)VRBO
Historic Inn: Romantic Couple Stay in Key West's Hidden Gem - Pools & Patio
- 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 $635 per night (USD)VRBO
From $458 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 $458 per night (USD)VRBO
From $938 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 $938 per night (USD)VRBO
From $1674 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 $1674 per night (USD)VRBO
From $594 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 $594 per night (USD)VRBO
From $486 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 $486 per night (USD)VRBO
From $610 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 $610 per night (USD)VRBO
From $764 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 $764 per night (USD)VRBO
From $480 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 $480 per night (USD)VRBO
From $791 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 $791 per night (USD)VRBO
From $594 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 $594 per night (USD)VRBO
From $486 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 $486 per night (USD)VRBO
From $1256 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 $1256 per night (USD)VRBO
From $2052 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 $2052 per night (USD)VRBO
From $843 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 $843 per night (USD)VRBO
From $655 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 $655 per night (USD)VRBO
From $1405 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 $1405 per night (USD)VRBO
From $568 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 $568 per night (USD)VRBO
From $937 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 $937 per night (USD)VRBO
From $1295 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 $1295 per night (USD)VRBO
From $522 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 $522 per night (USD)VRBO
From $596 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 $596 per night (USD)VRBO
From $422 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 $422 per night (USD)VRBO
From $711 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 $711 per night (USD)VRBO
From $663 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 $663 per night (USD)VRBO
From $729 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 $729 per night (USD)VRBO
From $1830 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 $1830 per night (USD)VRBO
From $2052 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 $2052 per night (USD)VRBO
From $1007 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 $1007 per night (USD)VRBO
From $1373 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 $1373 per night (USD)VRBO
Click For PricingVRBO
Snowbird-friendly condo with heated pool, patio lounge, water view, yard, & W\/D
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Key to Tranquility Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For PricingVRBO
From $184 per night (USD)Expedia
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 $184 per night (USD)Expedia
From $2146 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 $2146 per night (USD)VRBO
From $1698 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 $1698 per night (USD)VRBO
From $747 per night (USD)VRBO
Everything Key West has to offer @ Mango Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This historic Conch house is an excellent vacation home which has been thoughtfully remodeled to provide the best in mod ...
From $747 per night (USD)VRBO
From $312 per night (USD)VRBO
A Bit of Heaven is the perfect monthly rental in Key West
- Bedrooms:
- 3
- 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 $312 per night (USD)VRBO
From $342 per night (USD)VRBO
Old Town Key West Hideaway with Poolside Fun
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $342 per night (USD)VRBO
From $342 per night (USD)VRBO
Romantic Key West Lodge with Outdoor Pool & Stunning Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $342 per night (USD)VRBO
From $394 per night (USD)VRBO
Heart of Key West: Unique Stay with Outdoor Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $394 per night (USD)VRBO
From $615 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 $615 per night (USD)VRBO
From $3804 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 $3804 per night (USD)VRBO
From $1823 per night (USD)Expedia
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $1823 per night (USD)Expedia
From $589 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 $589 per night (USD)VRBO
From $1097 per night (USD)VRBO
Modern Elegance at Windsor Townhomes #5
- Bedrooms:
- 4
- 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 $1097 per night (USD)VRBO
From $1431 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 $1431 per night (USD)VRBO
From $724 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 $724 per night (USD)Expedia
From $378 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 $378 per night (USD)VRBO
From $795 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 $795 per night (USD)Expedia
From $769 per night (USD)VRBO
Hollinsed House Studio - Great Location!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $769 per night (USD)VRBO
From $1122 per night (USD)VRBO
Spacious Townhome on Windsor Lane 3\/3.5
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Windsor Townhomes #3! Once you enter this beautifully decorated oasis…your vacation begins. This townhome has ...
From $1122 per night (USD)VRBO
From $208 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 $208 per night (USD)VRBO
From $378 per night (USD)VRBO
ANNA MARIA HAVEN - Renovated 3bd\/3ba Conch Monthly rental
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This newly remodeled Conch house is located on Olivia Street in Old Town Key West just two and a half blocks from World ...
From $378 per night (USD)VRBO
From $440 per night (USD)VRBO
Paradise Awaits @ SOLEIL CHALET
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Your own private paradise awaits in this peaceful neighborhood just steps away from the buzz of Duval Street. “Soleil Ch ...
From $440 per night (USD)VRBO
From $922 per night (USD)VRBO
Windsor Townhomes #6 - Large pool 3B\/3.5 bath, 3 blocks to Duval
- Bedrooms:
- 4
- 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 $922 per night (USD)VRBO
From $444 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 $444 per night (USD)VRBO
From $375 per night (USD)VRBO
KNOT A WORRY so close to Duval at this monthly rental
- Bedrooms:
- 3
- 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 $375 per night (USD)VRBO
From $1110 per night (USD)VRBO
Casa Loca - so close to Duval 3bd\/2ba private home
- Bedrooms:
- 3
- 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 $1110 per night (USD)VRBO
From $258 per night (USD)VRBO
In the heart of Old Town lies the HAVEN HOUSE
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Haven House provides the perfect home base to be near the center of everything but be able to retreat to home and watch ...
From $258 per night (USD)VRBO
From $831 per night (USD)VRBO
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 $831 per night (USD)VRBO
From $1140 per night (USD)VRBO
Relax in Style at Windsor Townhomes #4
- Bedrooms:
- 4
- 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 $1140 per night (USD)VRBO
From $468 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 $468 per night (USD)VRBO
From $295 per night (USD)Expedia
LA CASITA EN CIMA~ Enjoy Key West in this lovely gem with a heated pool.
- Bedrooms:
- 2
- 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 $295 per night (USD)Expedia
From $376 per night (USD)VRBO
**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 $376 per night (USD)VRBO
From $458 per night (USD)Expedia
**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 $458 per night (USD)Expedia
From $360 per night (USD)VRBO
Boomerang Boathouse in Key West
- Bedrooms:
- 3
- 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 $360 per night (USD)VRBO
From $416 per night (USD)Expedia
Cozy 2-bedroom cottage in Old Town Key West, with shared pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This memorable cottage is the perfect home base for your trip to Key West. With 2 bedrooms, including 1 king bed and 1 q ...
From $416 per night (USD)Expedia
From $562 per night (USD)VRBO
THREE ARCHES IN PARADISE~ A Mediterranean marvel in a walkable location!
- Bedrooms:
- 4
- 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 $562 per night (USD)VRBO
From $652 per night (USD)Expedia
Pool, Pet Friendly, & Near Duval - Coastal Rose
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $652 per night (USD)Expedia
From $474 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 $474 per night (USD)VRBO
From $1128 per night (USD)Expedia
Pet Friendly, & Near Duval - Rose Key Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Escape to paradise with this luxurious Key West retreat, perfect for families and groups looking to unwind in s ...
From $1128 per night (USD)Expedia
From $921 per night (USD)VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Waterfront Sunset Harbor Resort, DUVAL STREET+Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! Additional $500-$1 ...
From $921 per night (USD)VRBO
From $229 per night (USD)Expedia
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 $229 per night (USD)Expedia
From $863 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 $863 per night (USD)VRBO
From $5625 per night (USD)VRBO
Key West Hyatt Charming 2-bedroom resort with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
From $5625 per night (USD)VRBO
Key West Studio Charming resort with WiFi, AC, fitness room
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)VRBO
From $513 per night (USD)VRBO
Stunning Key West Stay Perfect for a Romantic Escape! Outdoor Pool
- 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 $513 per night (USD)VRBO
From $219 per night (USD)VRBO
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 $219 per night (USD)VRBO
From $424 per night (USD)Expedia
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 $424 per night (USD)Expedia
From $690 per night (USD)VRBO
Relax in Romantic Lodge w\/ Pool Minutes from Vibrant Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $690 per night (USD)VRBO
From $435 per night (USD)VRBO
Modern Lodge w\/ Outdoor Pool Near Attractions Ideal for Family Fun
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $435 per night (USD)VRBO
From $883 per night (USD)VRBO
2 Rooms for the whole family w\/ Pool access! Near Duval St. and Museums
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $883 per night (USD)VRBO
From $794 per night (USD)VRBO
2 Bedroom Suite w\/ Outdoor Pool in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $794 per night (USD)VRBO
From $516 per night (USD)VRBO
Heron Hideaway - Charming 1st-Floor Unit, Shared Pool, Private Hot Tub, Near Duval St & Beaches
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Heron Hideaway, a charming 1st-floor condo nestled in the desirable Meadows area of Key West. Just six blocks ...
From $516 per night (USD)VRBO
From $2315 per night (USD)Expedia
Pool & Parking, & Near Duval - The Rigby House
- Bedrooms:
- 7
- 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 $2315 per night (USD)Expedia