Key West National Wildlife Refuge Rentals
- From $646 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 $646 per night (USD)VRBO
- From $490 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 $490 per night (USD)VRBO
- From $667 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 $667 per night (USD)VRBO
- From $790 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 $790 per night (USD)VRBO
- From $477 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 $477 per night (USD)VRBO
- From $991 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 $991 per night (USD)VRBO
- From $646 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 $646 per night (USD)VRBO
- From $490 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 $490 per night (USD)VRBO
- From $1439 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 $1439 per night (USD)VRBO
- From $2302 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 $2302 per night (USD)VRBO
- From $963 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 $963 per night (USD)VRBO
- From $789 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 $789 per night (USD)VRBO
- From $1533 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 $1533 per night (USD)VRBO
- From $552 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 $552 per night (USD)VRBO
- From $936 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 $936 per night (USD)VRBO
- From $1577 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 $1577 per night (USD)VRBO
- From $491 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 $491 per night (USD)VRBO
- From $568 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 $568 per night (USD)VRBO
- From $481 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 $481 per night (USD)VRBO
- From $766 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 $766 per night (USD)VRBO
- From $649 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 $649 per night (USD)VRBO
- From $768 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 $768 per night (USD)VRBO
- From $1919 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 $1919 per night (USD)VRBO
- From $2302 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 $2302 per night (USD)VRBO
- From $1022 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 $1022 per night (USD)VRBO
- From $1399 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 $1399 per night (USD)VRBO
- From $1345 per night (USD)
VRBO
Studio Sleeps 2 | Pool | Beachfront | RW
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Galleon Resort offers a multitude of accommodations in studio, one-bedroom and two-bedroom configurations. Studios h ...
From $1345 per night (USD)VRBO
- From $1500 per night (USD)
VRBO
Key West•Beachfront•Concierge•Fast WiFi•Luxury RW
- 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 $1500 per night (USD)VRBO
- From $995 per night (USD)
VRBO
1 HSH Keys, Key West
- 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 $995 per night (USD)VRBO
- From $838 per night (USD)
VRBO
2\/2 Sleeps 6 | Comfy Beds | Beach | Pool RW
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $838 per night (USD)VRBO
- From $795 per night (USD)
VRBO
1\/1 Sleeps 2 | Pool | Hot Tub | Concierge RW
- 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 $795 per night (USD)VRBO
- From $365 per night (USD)
Expedia
Escape to Key West! And stay at the Rose Key Cottage so close to Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Rose Key Cottage Escape, to your slice of paradise in Key West! Situated just half a block from the iconi ...
From $365 per night (USD)Expedia
- From $372 per night (USD)
VRBO
Charm is on order at Rose Key Cottage! Come check it out!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your piece of paradise! Rose Key Cottage is a delightful, historic home nestled in the heart of Old Town Key ...
From $372 per night (USD)VRBO
- From $208 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 $208 per night (USD)Expedia
- From $222 per night (USD)
VRBO
SWEET LIKE SUMMERTIME ~ 3 BR\/2Ba Home w\/ Pool and Yard!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
CLASSIC UPDATED CHARMER... Welcome to this beautifully renovated 3 bedroom 2 bath pool home, located in the heart of Bah ...
From $222 per night (USD)VRBO
- From $900 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 $900 per night (USD)VRBO
- From $549 per night (USD)
VRBO
SWEET DREAMS ARE MADE OF 'THE KEYS' ~ Bahama Village 2 BR\/2 Ba Home w\/ Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
BAHAMA VILLAGE BEAUTY... This dream of a home is yours for the ultimate escape to southernmost paradise! Located in the ...
From $549 per night (USD)VRBO
- From $269 per night (USD)
Expedia
CHANGES IN LATITUDES ~ Renovated 3 BR\/2.5 Ba Home w\/ Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
MODERN MERGES WITH HISTORIC CHARM... Discover a blend of sleek contemporary elegance that interweaves with the rich tape ...
From $269 per night (USD)Expedia
- Click For Pricing
VRBO
Waterfront Retreat, Offshore Boat Races, Near RWO Mole, 3 Night, Hyatt, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Imbibe in the relaxed Key West lifestyle from a coveted location nestled in the heart of Key West’s famed Old Town at th ...
Click For PricingVRBO
- Click For Pricing
VRBO
Waterfront Retreat, Offshore Boat Races, Near RWO Mole, 7 Nights Hyatt Sleeps 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Imbibe in the relaxed Key West lifestyle from a coveted location nestled in the heart of Key West’s famed Old Town at th ...
Click For PricingVRBO
- From $677 per night (USD)
VRBO
SALTWATER SOPHISTICATION ~ Renovated 4 BR, 4.5 Ba Downtown Home w\/ Pool!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 9
PREMIER HISTORICAL RETREAT... Just steps from the Seaport District hosting the best waterfront restaurants and world fam ...
From $677 per night (USD)VRBO
- From $255 per night (USD)
Expedia
THE GOOD LIFE ~ Charming 1 Bedroom, 1 Bath Truman Annex Condo!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
COZY VALUE IN TRUMAN ANNEX… This one bedroom, one bath condo is located in The Shipyard, a neighborhood of the coveted T ...
From $255 per night (USD)Expedia
- From $469 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 $469 per night (USD)VRBO
- From $664 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 $664 per night (USD)VRBO
- From $300 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 $300 per night (USD)VRBO
- From $744 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 $744 per night (USD)Expedia
- From $561 per night (USD)
VRBO
\"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 $561 per night (USD)VRBO
- From $483 per night (USD)
Expedia
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $483 per night (USD)Expedia
- From $643 per night (USD)
VRBO
Hyatt Sunset Harbor, overlooking the Gulf of Mexico.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Reservations are available in weekly (7 night) increments with arrivals and departures on Fridays, Saturdays, and Sunday ...
From $643 per night (USD)VRBO
- From $499 per night (USD)
VRBO
★Family Friendly 2BR Condo 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 $499 per night (USD)VRBO
- From $1295 per night (USD)
VRBO
Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $1295 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Stone's Throw ~ Beautiful home in a great location with shared pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CLOSE TO THE FUN.... This Adorable Conch Cottage is a “Stone’s Throw” from everything that Key West has to offer! Liter ...
From $175 per night (USD)VRBO
- From $904 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 $904 per night (USD)VRBO
- From $1758 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 $1758 per night (USD)Expedia
- From $757 per night (USD)
VRBO
SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Home in Desirable Downtown Location!
- 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 $757 per night (USD)VRBO
- From $831 per night (USD)
Expedia
STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!
- Bedrooms:
- 2
- Bathrooms:
- 4
- 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 $831 per night (USD)Expedia
- From $451 per night (USD)
VRBO
FOUNDRY 7- Weekly Vacation Rental - Shared Pool - 2BD\/2.5BA RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
WELCOME TO FOUNDRY 7! Escape to the historic and luxurious neighborhood of Truman Annex in Key West, where you'll find ...
From $451 per night (USD)VRBO
- From $256 per night (USD)
Expedia
THE QUARTERDECK ~ Colorful & Comfortable 2Ba\/ 1Ba Unit in The Shipyard!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
COMFORT AND VALUE IN TRUMAN ANNEX… This newly renovated two bedroom condo is located in The Shipyard, a neighborhood of ...
From $256 per night (USD)Expedia
- Click For Pricing
Expedia
Paradise on Porter- Weekly Rental
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Paradise on Porter is a wonderful vacation townhome located in the desirable Truman Annex area of downtown Key West. Th ...
Click For PricingExpedia
- From $826 per night (USD)
VRBO
PINEAPPLE COTTAGE: 2BR\/2BA-Pvt Pool -1\/2 block to Duval- RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
WELCOME TO PINEAPPLE COTTAGE! The Pineapple Cottage is a charming two-bedroom, two-bathroom home located in Old Town K ...
From $826 per night (USD)VRBO
- From $384 per night (USD)
VRBO
A Slice of Paradise! @ the Shipyard ~ Now 20% off for April & May new bookings!
- 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 $384 per night (USD)VRBO
- From $419 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 $419 per night (USD)VRBO
- From $375 per night (USD)
VRBO
PALMS AWAY ~ Truman Annex Townhome with Outdoor Patio and Community Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
STEPS TO IT ALL... Peaceful surroundings of swaying palm trees and picturesque white picket fences invite you in to this ...
From $375 per night (USD)VRBO
- From $342 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 $342 per night (USD)VRBO
- From $500 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 $500 per night (USD)VRBO
- From $1132 per night (USD)
Expedia
BAHAMA DREAMING ~ Incredibly Located 3 Bedroom, 2 Bath w\/ Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BEGIN YOUR ISLAND ESCAPE... Come get lost in the magic of this captivating island retreat offering modern amenities with ...
From $1132 per night (USD)Expedia
- From $1043 per night (USD)
VRBO
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 $1043 per night (USD)VRBO
- From $112 per night (USD)
Expedia
PINEAPPLE COTTAGE ~ Adorable, Updated Cottage in Old Town with Heated Pool!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
RELAXED DOWNTOWN LIVING... Envelop yourself in true island living in this cute cottage just for the two of you. Located ...
From $112 per night (USD)Expedia
- Click For Pricing
VRBO
Walk to Duval St and Mallory Square - 2BR Condo at Heart of Old Town Key West
- 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 ...
Click For PricingVRBO
- From $1063 per night (USD)
VRBO
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 $1063 per night (USD)VRBO
- From $1500 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 $1500 per night (USD)VRBO
- From $221 per night (USD)
VRBO
Banyan Court downtown condo- 2 bedroom, 2.5 bath, walkable, parking, pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $221 per night (USD)VRBO
- From $251 per night (USD)
VRBO
Shipyard Truman Annex 1st Floor End Unit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A Change In Latitudes is a non-smoking, 1st floor end unit in the peaceful and serene section of Shipyard. All the amen ...
From $251 per night (USD)VRBO
- From $600 per night (USD)
VRBO
** Waterfront - Two Blocks From Duval Street & Mallory Square**
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $600 per night (USD)VRBO
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VRBO
Galleon Resort - Balcony Overlooking Marina w\/ Stair to Boardwalk, Sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WATERFRONT TWO BEDROOMS, 2 BATHS, FULL KITCHEN IN KEY WEST HISTORIC SEAPORT Condo type unit with an area of 1300 squar ...
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- From $895 per night (USD)
VRBO
SEAPORT SERENITY at Galleon Resort near Mallory Square—King Suite-Beach-Pool-BBQ
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
OCEANFRONT CASUAL LUXURY CONDO RENTAL 40 FT FROM THE WATER WITH BREATHTAKING & UNOBSTRUCTED VIEWS OF KEY WEST HARBOR AND ...
From $895 per night (USD)VRBO
- From $269 per night (USD)
VRBO
Quick 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 $269 per night (USD)VRBO
- From $267 per night (USD)
Expedia
SMOOTH SAILING ~ 2 Bedroom, 1 Bath Renovated Condo w\/ Community Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A TRUMAN ANNEX DREAM... Come discover this beautifully renovated condo within the desirable Shipyard neighborhood in the ...
From $267 per night (USD)Expedia
- From $129 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 $129 per night (USD)VRBO
- From $639 per night (USD)
VRBO
Hyatt Sunset Harbor, overlooking the stunning and beautiful Gulf of Mexico.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
These are 7-night rentals, with check-in on Fridays, Saturdays and Sundays only. Discover a relaxing oasis overlooking ...
From $639 per night (USD)VRBO
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VRBO
Studio unit at the Galleon Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Galleon offers studio type units that can sleep two to four people depending on the unit. All units are air conditio ...
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VRBO
The Galleon Resort Nov 2 - Nov 9, 2019\/ Boat Week 2019 Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Great unit for boat week in Key West. Saturday to Saturday availability. 2 bedroom condo at The Galleon Resort sleeps 6 ...
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- From $766 per night (USD)
VRBO
★Family Friendly 2BR Condo 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 $766 per night (USD)VRBO
- From $562 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 $562 per night (USD)VRBO
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VRBO
Galleon Resort 2bed\/2bath
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 bed/2bath overlooking Marina. King master bedroom. Queen in 2nd bedroom. Sleeper sofa in living room. Jacuzzi tub in m ...
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VRBO
THE GALLEON - UNIT B-42
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Galleon Resort, Unit B-42. Available Saturday Nov 9, 2019 thru Saturday Nov 16, 2019 (7 nights) . Sleeps six. Pool a ...
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- From $351 per night (USD)
VRBO
A Caribbean Alternative
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
A Caribbean Alternative is a wonderful vacation townhome located in the desirable Truman Annex area of downtown Key West ...
From $351 per night (USD)VRBO
- From $765 per night (USD)
Expedia
ISLE AZURE ~ Charming 3 Bed\/3 Bath with Private Pool & Spa 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 $765 per night (USD)Expedia
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VRBO
Welcome Aboard! Prime location in Key West on a 46' Luxury Catamaran
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Join us on a 46' luxury sailing catamaran, The Space Between, enjoying all the comforts of home and the added beauty and ...
Click For PricingVRBO
- From $1225 per night (USD)
VRBO
Steps From Duval St. Historical Charm Meets Modern Design In Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Perfectly located and fully remodeled, Octopus's Garden is steps from Duval Street and the home of Ernest Hemmingway. ...
From $1225 per night (USD)VRBO
- From $315 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex 2 bedroom 2 bath Shipyard Condo at MM 0!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 2 bath {queen and ...
From $315 per night (USD)VRBO
- From $1752 per night (USD)
Expedia
STARS AND STRIPES ~ Magnificent Home Located In The Heart of Old Town!
- Bedrooms:
- 4
- Bathrooms:
- 8
- 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 $1752 per night (USD)Expedia
- From $219 per night (USD)
VRBO
Eleanor's Place in Key West Old Town - Dogs Ok with Parking.
- 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 $219 per night (USD)VRBO
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VRBO
Galleon Key West Resort - Waterfront Marina 2-Bedroom Suite + Beach + Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Best view in Key West! Sitting atop the Galleon Resort in a penthouse room with a clear view of the Galleon Marina and h ...
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- From $300 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 $300 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $292 per night (USD)Expedia
- From $175 per night (USD)
VRBO
SPARKLING Old Town KW PRIVATE 3BR Home Lagoon Pool FREE Bikes Steps to Duval
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A colorful three bedroom, two full bath, private, and historic home is a wonderful spot to vacation, live like a local, ...
From $175 per night (USD)VRBO
- From $359 per night (USD)
Expedia
TROPICAL FRONT ~ Remodeled 2 BR, 2.5 Ba w\/ Parking in Perfect Location!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
IN THE HEART OF IT ALL… A perfect location within a peaceful setting, this updated home allows for extraordinary moments ...
From $359 per night (USD)Expedia
- From $329 per night (USD)
VRBO
BLUE BUNGALOW ~ 2 Bedroom Townhome in Truman Annex Community with Pool!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
PICTURE PERFECT… Swaying palms and a picturesque white picket fence outline this tropical retreat luring you in to your ...
From $329 per night (USD)VRBO
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Expedia
Price Reduction!!! Penthouse Suite @ KW, Galleon Resort, Avail 6\/29 - 7\/6\/2024
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The Galleon Resort is the best location - Old Town Key West, walking location to all the bars, many high quality restaur ...
Click For PricingExpedia