Key West National Wildlife Refuge Rentals
From $422 per night (USD)VRBO
Elegant Boutique Room w\/ Private Patio & Garden - Duval Street steps away
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $422 per night (USD)VRBO
From $1127 per night (USD)Expedia
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 $1127 per night (USD)Expedia
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 $519 per night (USD)VRBO
Stylish Boutique Room w\/ 2 Queen Beds - Access Pool & Poolside Bar
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $519 per night (USD)VRBO
From $1779 per night (USD)VRBO
2 Family-friendly Units, Complimentary Breakfast, Outdoor Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1779 per night (USD)VRBO
From $1035 per night (USD)VRBO
Perfect for Groups! 2 Pet-friendly Units, Free Breakfast, Outdoor Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1035 per night (USD)VRBO
From $527 per night (USD)VRBO
**A BEACHY VIEW @ THE TRUMAN ANNEX IN KEY WEST**
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come and relax in this 2-bedroom 1 bath, first floor with 3 flat screen TV's, custom kitchen, backyard tropical paradise ...
From $527 per night (USD)VRBO
From $685 per night (USD)Expedia
~Hibiscus Cottage~ Adults Only cottage near Duval with shared pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: Welcome to your private rocking chair front porch and tropical, Adult Only setting! As you enter your quai ...
From $685 per night (USD)Expedia
From $265 per night (USD)VRBO
Cozy on Caroline - Key West Seaport
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Experience the quintessential Key West lifestyle in this charming one-bedroom, two-bathroom apartment that perfectly bal ...
From $265 per night (USD)VRBO
From $416 per night (USD)Expedia
Southern Skies, Stylish Home in Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the paradise of Southern Skies, an elegant 3 bedroom and 2.5 bath home nestled in the heart of Key West's His ...
From $416 per night (USD)Expedia
From $261 per night (USD)VRBO
Charming 1923 2 Bedroom, 1 Bath home with bonus loft.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to The Emma House! A delightful 1923 Key West retreat located in the heart of historic and vibrant Bahama Villa ...
From $261 per night (USD)VRBO
From $1069 per night (USD)Expedia
Ocean View Sunset Harbor Resort Timeshare available 1 week only Mar30-Apr6, 2025
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in between Truman Annex, Duval St. and Mallory Square- This lovely Key West townhouse boasts 2 bedrooms - one w ...
From $1069 per night (USD)Expedia
From $504 per night (USD)VRBO
Zen Villa - A Luxurious 3-bedroom Sanctuary with WiFi & a Pool in Old Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
Zen Villa - A Luxe Retreat in the Heart of Old Key West! Tucked away on a quiet lane just steps from the vibrant heartbe ...
From $504 per night (USD)VRBO
From $375 per night (USD)Expedia
Jerry's Escape - Truman @ Duval | Cozy Studio Perfect for Couples
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Truman @ Duval - Unit C | Cozy Studio Perfect for Couples Experience your perfect romantic retreat, offering a charming ...
From $375 per night (USD)Expedia
From $581 per night (USD)VRBO
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Truman @ Duval - Unit D | Two-Bedroom with Full Kitchen & Prime Location Welcome to your perfect family getaway in the ...
From $581 per night (USD)VRBO
From $604 per night (USD)VRBO
Charming Hideaway with Pool – Walk to Duval St & Local Attractions
- 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 $604 per night (USD)VRBO
From $612 per night (USD)VRBO
Sunny Florida Escape with Pool, Beach Access & Stunning Views
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $612 per night (USD)VRBO
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 $1824 per night (USD)VRBO
3| Galleon | Marina | Spa | Hot Tub | Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $1824 per night (USD)VRBO
From $2236 per night (USD)VRBO
Sunset Harbor | Marina | Hot Tub | Pool | Concierge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $2236 per night (USD)VRBO
From $1941 per night (USD)VRBO
The Banyan | Concierge | Beach Access | Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of historic Old Town Key West, The Banyan Resort is a charming escape set on a mid-1800s estate ste ...
From $1941 per night (USD)VRBO
From $11524 per night (USD)VRBO
Galleon | Hot Tub | Marina | Lux Resort | Concierge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $11524 per night (USD)VRBO
From $2236 per night (USD)VRBO
Sunset Harbor | Hyatt | Hot Tub | Pool | Marina | Lux Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $2236 per night (USD)VRBO
From $1839 per night (USD)VRBO
Galleon | Marina | Lux Resort | Pool | Hot Tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $1839 per night (USD)VRBO
From $1839 per night (USD)VRBO
Galleon | Marina | Concierge | Hot Tub | Spa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled along the sparkling Gulf of Mexico in historic Old Town, The Galleon Resort places you in the heart of Key West’ ...
From $1839 per night (USD)VRBO
From $933 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 $933 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 Florida Charming 1-bedroom resort with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $1462 per night (USD)VRBO
No secrets at Pilar's Secret - Just a great location!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Pilar’s Secret is hidden away in the heart of Old Town Key West just half a block off the famous Duval Street. This secl ...
From $1462 per night (USD)VRBO
From $1823 per night (USD)VRBO
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)VRBO
From $2140 per night (USD)VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to The Galleon Resort in Key West, where paradise meets luxury at the southernmost tip of the United States. In ...
From $2140 per night (USD)VRBO
From $1189 per night (USD)VRBO
Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1189 per night (USD)VRBO
From $1664 per night (USD)VRBO
Sunset Harbor Resort & Spa, Hot Tub, Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1664 per night (USD)VRBO
From $1308 per night (USD)VRBO
Sunset Harbor Resort, Marina, In Town, Hot Tub, Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1308 per night (USD)VRBO
From $310 per night (USD)Expedia
THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w\/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
HIDDEN GEM... The perfect location for guests who want to walk and bike to everything Key West has to offer. Modern cot ...
From $310 per night (USD)Expedia
From $484 per night (USD)VRBO
SWEET LIKE SUMMERTIME ~ 3 BR\/2Ba Home w\/ Pool and Yard!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
CLASSIC CHARMER... Welcome to this beautifully renovated 3 bedroom 2 bath pool home, located in Bahama Village. This cla ...
From $484 per night (USD)VRBO
From $1279 per night (USD)VRBO
Waterfront Sunset Harbor Resort Near Old Town+Amenities: 2BR FindingMeili
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to FindingMeili🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! An Additional Savings from $500 ...
From $1279 per night (USD)VRBO
From $339 per night (USD)VRBO
THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
COZY VALUE IN TRUMAN ANNEX… This 2nd Floor one bedroom, one bath condo is located in The Shipyard, a neighborhood of the ...
From $339 per night (USD)VRBO
From $534 per night (USD)Expedia
\"Tranquility \" At Ann Street Gardens Steps From Duval
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Location is ideal for this wonderful one bedroom retreat. A lush, inviting compound created so owners and guests could e ...
From $534 per night (USD)Expedia
From $714 per night (USD)VRBO
Hyatt Sunset Harbor, overlooking the Gulf of Mexico; 2 bd villa!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Concierge Realty is proud to present luxury villas at Hyatt Sunset Harbor! **Reservations are available in weekly (7 ni ...
From $714 per night (USD)VRBO
From $999 per night (USD)Expedia
Craig & Cindy's 4 Bedroom Key West Truman Annex Porter House with private pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The two story Truman Annex Porter House is the largest of our Key West properties and features 4 bedrooms and a private ...
From $999 per night (USD)Expedia
From $524 per night (USD)VRBO
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items ...
From $524 per night (USD)VRBO
From $868 per night (USD)VRBO
Rose Lane Villas - Villa Aqua - 2 King 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 $868 per night (USD)VRBO
From $389 per night (USD)VRBO
Enjoy More Privacy in a Truman Annex End Unit Townhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Contact us about special Summer Rates! Absolute Best Location! Our Townhome is set in the tranquil verdant gardens of ...
From $389 per night (USD)VRBO
From $2064 per night (USD)Expedia
Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $2064 per night (USD)Expedia
From $1285 per night (USD)VRBO
STRIPES ~ Delightful Condo w\/Shared Pool in the Heart of Old Town Key West!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key W ...
From $1285 per night (USD)VRBO
From $2326 per night (USD)Expedia
SOUTHERNMOST BELLE~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
LUXURY IN OLD TOWN... Grand home in the Historic Seaport area of Old Town Key West. Tucked behind a canopy of palms this ...
From $2326 per night (USD)Expedia
From $1179 per night (USD)VRBO
SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Annex Home w\/Private Heated Pool!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
PREMIER TROPICAL RETREAT... Come spoil yourself in this conveniently located two-story home tucked away on a quiet lane ...
From $1179 per night (USD)VRBO
From $1067 per night (USD)Expedia
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
When you do not need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key ...
From $1067 per night (USD)Expedia
From $472 per night (USD)VRBO
FOUNDRY 7- Weekly Vacation Rental - Shared Pool - 2BD\/2.5BA RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
WELCOME TO FOUNDRY 7! Escape to the historic and luxurious neighborhood of Truman Annex in Key West, where you'll find ...
From $472 per night (USD)VRBO
From $351 per night (USD)Expedia
THE QUARTERDECK ~ Colorful & Comfy 2nd Floor 2Ba\/ 1Ba Unit in The Shipyard!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
COMFORT AND VALUE IN TRUMAN ANNEX… This newly renovated 2nd floor two bedroom condo is located in The Shipyard, a neighb ...
From $351 per night (USD)Expedia
From $1043 per night (USD)VRBO
PINEAPPLE COTTAGE: 2BR\/2BA-Pvt Pool -1\/2 block to Duval- RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town K ...
From $1043 per night (USD)VRBO
From $411 per night (USD)VRBO
A Slice of Paradise! @ the Shipyard Palms!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of Old Town, with the beautiful community of private homes and condominiums of Truman Annex, this Shipyard ...
From $411 per night (USD)VRBO
From $497 per night (USD)VRBO
Ann Street Cottage: A bright and airy home near Duval Street
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom c ...
From $497 per night (USD)VRBO
From $470 per night (USD)Expedia
PALMS AWAY ~ Truman Annex Townhome with Outdoor Patio and Community Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
STEPS TO IT ALL... Peaceful surroundings of swaying palm trees and picturesque white picket fences invite you in to this ...
From $470 per night (USD)Expedia
From $406 per night (USD)VRBO
Zen Cigar Maker Cottage, magical serpentine pool, serene landscaping, pkg\/bikes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the Key West Shire! A sublime sanctuary where all your worldly troubles melt away and relaxation is paramoun ...
From $406 per night (USD)VRBO
From $549 per night (USD)VRBO
Incredible 2BR Penthouse condo on Front Street with amazing amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort is one of Key West's best resorts. Located on Front Street in front of the Marina, it has a large wat ...
From $549 per night (USD)VRBO
From $1219 per night (USD)VRBO
BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w\/ Private Heated Pool!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
BEGIN YOUR ISLAND ESCAPE... Come get lost in the magic of this captivating island retreat offering modern amenities with ...
From $1219 per night (USD)VRBO
From $1294 per night (USD)Expedia
Secret Villa II @ Old Town: with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa II - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own pri ...
From $1294 per night (USD)Expedia
From $165 per night (USD)VRBO
PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
RELAXED DOWNTOWN LIVING... Envelop yourself in true island living in this cute cottage just for the two of you. Located ...
From $165 per night (USD)VRBO
From $1226 per night (USD)Expedia
Secret Villa I @ Old Town with Private Pool, close to Duval!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
- Secret Villa I - A Newly Renovated, Private Sanctuary, Centrally Located off of Duval Street with your very own priv ...
From $1226 per night (USD)Expedia
From $2186 per night (USD)VRBO
Key West Suites Hotel # 205
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used t ...
From $2186 per night (USD)VRBO
From $427 per night (USD)Expedia
SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w\/ Community Pool!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
A TRUMAN ANNEX DREAM... Come discover this beautifully renovated condo within the desirable Shipyard neighborhood in the ...
From $427 per night (USD)Expedia
From $217 per night (USD)VRBO
BELLA VITA ~ 2\/1.5 located in the Truman Annex with a community pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
IDEAL LOCATION IN GREAT COMMUNITY... Enjoy your stay at the President's Walk at Truman Annex. This well manicured commu ...
From $217 per night (USD)VRBO
From $703 per night (USD)VRBO
Hyatt Sunset Harbor, 2BD overlooking the stunning and beautiful Gulf of Mexico!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Concierge Realty is proud to present luxury villas at Hyatt Sunset Harbor! **Reservations are available in weekly (7 ni ...
From $703 per night (USD)VRBO
From $872 per night (USD)VRBO
SEAPORT SERENITY at Galleon Resort-Beach-Pool-King Suite-BBQ-Kitchen views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
OCEANFRONT CASUAL LUXURY CONDO RENTAL 40 FT FROM THE WATER WITH BREATHTAKING & UNOBSTRUCTED VIEWS OF KEY WEST HARBOR AND ...
From $872 per night (USD)VRBO
From $241 per night (USD)VRBO
Banyan Court downtown condo- 2 bedroom, 2.5 bath, walkable, parking, pool
- Bedrooms:
- 3
- 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 $241 per night (USD)VRBO
From $214 per night (USD)VRBO
Shipyard Truman Annex; 620 Thomas St. 1st Floor AVAILABLE SEPT 2025
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A Change In Latitudes is a non-smoking, 1st floor end unit in the serene section of Shipyard, Truman Annex. All the ame ...
From $214 per night (USD)VRBO
From $608 per night (USD)VRBO
** Waterfront - Two Blocks From Duval Street & Mallory Square**
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This condo located right on the water in Building 5 (Unit 531) - top floor - at the Hyatt Sunset Harbor, is a 2 bedroom, ...
From $608 per night (USD)VRBO
From $370 per night (USD)VRBO
Minute walk to pool! 5 Star Preferred, 3 bikes, a pool, parking, and 2 porches!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
BIlly's Blue Heaven is fresh, clean and Pristine. We have updated the condo with all new paint, a new Smart Tv in the ...
From $370 per night (USD)VRBO
From $660 per night (USD)VRBO
Near Duval - Tiki Bar - Private Beach - 2BR Condo - Old Town Key West - Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $660 per night (USD)VRBO
From $868 per night (USD)VRBO
★2BR Resort Villa at Heart of Old Town Key West- Sleeps 6!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $868 per night (USD)VRBO
From $1950 per night (USD)Expedia
Perfect Location, Private Heated Pool & Pristine Luxury Home!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Perfectly located and fully remodeled, Octopus's Garden is steps from Duval Street and the home of Ernest Hemmingway. ...
From $1950 per night (USD)Expedia
From $862 per night (USD)VRBO
ISLE AZURE ~ Charming 3 Bed\/3 Bath with Private Pool in Truman Annex!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
QUINTESSENTIAL OLD TOWN CHARM… Imagine pulling up to a picture-perfect gated community, lined by white picket fences and ...
From $862 per night (USD)VRBO
From $338 per night (USD)VRBO
Lock-Out Unit at the Galleon Resort - Best Resort Location In KW
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio(lock-out) for rent 5th floor. The Galleon Resort has its own marina, fishing charters on-site, tiki bar that serv ...
From $338 per night (USD)VRBO
From $2605 per night (USD)VRBO
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
- Bedrooms:
- 4
- Bathrooms:
- 9
- Sleeps:
- 20
ABUNDANCE IN OLD TOWN... Majestic home in the Historic Seaport area of Old Town Key West. This is THE house to bring eve ...
From $2605 per night (USD)VRBO
From $415 per night (USD)VRBO
Eleanor's Place Key West Cottage in Historic Old Town - Dogs Ok
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
THE PROPERTY: "Eleanor's Place" has everything you might want on your monthly vacation to Key West, beginning with your ...
From $415 per night (USD)VRBO
From $389 per night (USD)VRBO
Craig & Cindy Key West Truman Annex 2 bedroom 2 bath Shipyard Condo at MM 0!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 2 bath {queen and ...
From $389 per night (USD)VRBO
From $346 per night (USD)Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $346 per night (USD)Expedia
From $549 per night (USD)VRBO
TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w\/ Parking in Perfect Location!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
IN THE HEART OF IT ALL… A perfect location within a peaceful setting, this updated home allows for extraordinary moments ...
From $549 per night (USD)VRBO
From $529 per night (USD)Expedia
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PICTURE PERFECT… Swaying palms and a picturesque white picket fence outline this tropical retreat luring you in to your ...
From $529 per night (USD)Expedia
From $731 per night (USD)VRBO
Penthouse Suite @ KW, Galleon Resort, Not Available in 2024-2025
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Galleon Resort is the best location - Old Town Key West, walking location to all the bars, many high quality restaur ...
From $731 per night (USD)VRBO
From $865 per night (USD)Expedia
Largest Shipyard Condo in the Truman Annex - over twice the size with a loft!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Shipyard PENTHOUSE! This unit was supposed to be 2 units but it was built as one larger unit plus two lofts were added. ...
From $865 per night (USD)Expedia
From $343 per night (USD)VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo w\/ balcony at Mile Marker 0!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $343 per night (USD)VRBO
From $274 per night (USD)VRBO
Banyan Court downtown condo- 2 bedroom, 2 bath, walkable, parking, pool
- 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 $274 per night (USD)VRBO
From $423 per night (USD)VRBO
Shipyard 197-Condo in Truman Annex-2 bedroom 1 bath, close to Duval w\/ pool
- Bedrooms:
- 1
- 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 $423 per night (USD)VRBO
From $396 per night (USD)VRBO
Truman Annex unit 254
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Key Lime has a large open kitchen, vaulted ceilings and tile floors throughout. This immaculate unit has two-bedrooms, 2 ...
From $396 per night (USD)VRBO
From $758 per night (USD)VRBO
The Galleon Resort, Waterfront Location, Well-equipped Two Bedroom Villa!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Please choose a Saturday check-in, all rentals will be in seven night increments. Bedding configuration may vary, depend ...
From $758 per night (USD)VRBO
From $1000 per night (USD)Expedia
Hyatt Sunset Harbor Resort for ONLY Sunday to Sunday Week's stay.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is for A WEEK'S Stay Only in a 2 Bedroom 2 Bathroom Villa for 6 People. Discover this relaxing oasis in the heart ...
From $1000 per night (USD)Expedia
From $402 per night (USD)VRBO
Heart of Downtown Key West Cottage With Off-Street Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
A Historic Cigar-Makers Conch Home, privately owned by a native hospitable family in the heart of Downtown, a few minut ...
From $402 per night (USD)VRBO
From $203 per night (USD)VRBO
2026 now available! SPARKLING Old Town PRIVATE 3BR Lagoon Pool& FIVE stars!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This colorful three bedroom, two full bath, private, and historic home is a wonderful spot to vacation, live like a loca ...
From $203 per night (USD)VRBO
From $636 per night (USD)VRBO
Namaste 'The Spirit Within Me Salutes The Spirit Within You'
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom B ...
From $636 per night (USD)VRBO
From $366 per night (USD)VRBO
Villa Nomade at Shipyard Condominiums
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Relax at Villa Nomade in luxurious surroundings. Featuring a fully equipped kitchen with bar seating and dining area. Th ...
From $366 per night (USD)VRBO
From $568 per night (USD)VRBO
Rose Lane Villas - Villa Alta - 1 bedroom - Sleeps 4 - Downtown Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 wit ...
From $568 per night (USD)VRBO
From $701 per night (USD)VRBO
Hyatt Sunset Harbour Resort-Prime location on Key West!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
All rentals will be in seven-night increments with a Friday through Sunday for check-in. Thank you for choosing Dash R ...
From $701 per night (USD)VRBO
From $343 per night (USD)VRBO
Cozy Piece of Key West History
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PERFECTLY located, 100 y-o "Conch" House, w AAA+ front-porch, and 3 full baths to go w 3 BRs... brand-new kitchen, compl ...
From $343 per night (USD)VRBO
From $390 per night (USD)Expedia
THE OLD SAPODILLA HOUSE ~ Pet Friendly Home in Historic Bahama Village
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
PERFECT GETAWAY JUST STEPS FROM DUVAL... Private family home with poolside cottage totals three bedrooms and three full ...
From $390 per night (USD)Expedia
From $346 per night (USD)VRBO
~ THE PINK HOUSE ~ Saline pool, lush privacy and 2 ensuites with balconies.
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 5
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $346 per night (USD)VRBO
From $557 per night (USD)VRBO
~FAIR WINDS @ THE FOUNDRY~ Frolic on Duval St then unwind in the shared pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
WEEKLY RENTAL: This property has a 7 night minimum stay. **Beginning January, 2026, Fair Winds will be a MONTHLY (28 n ...
From $557 per night (USD)VRBO