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177 Best cottages in Key West, FL
8.4 7 reviews
Key West, FL
12/21 – 01/18
$515/nighttotal: $14420 (28 )
~Royal Poinciana Cottage~ Come And Indulge Yourself In Some Kw Sunshine!
1 1
cottage , Key West
This pet-friendly Key West cottage, located in Old Town, is a short walk from Saint Mary Star of the Sea Church and the Key West Firehouse Museum, offering easy access to beaches and attractions like the Ernest Hemingway Home and Museum. The one-bathroom rental boasts a fully equipped kitchen, in-unit laundry, air conditioning, Wi-Fi, a private porch, and access to a shared pool; it comfortably sleeps two guests and includes on-site barbecue facilities.
9.6 394 reviews
Key West, FL
10/17 – 10/24
$829/nighttotal: $5803 (7 )
Pete's East Cottage: Cypress East Cottage Steps From Duval
1 2
cottage , Key West
This charming Key West cottage is located in Old Town, just a short walk from the Banana Cafe Restaurant and Coffee and Tea house, offering easy access to delicious food and drinks. The cottage boasts excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay. The cottage features a spacious living area with a spiral staircase leading to a loft bedroom, as well as a semi-private deck and lounge area for relaxation. Guests can enjoy the large kidney-shaped pool with a waterfall, a fully equipped kitchen, and the convenience of keyless entry.
9.4 172 reviews
Key West, FL
08/22 – 08/29
$362/nighttotal: $2534 (7 )
Conch Republic Consul General's Cottage.-historic District
2 2
cottage , Key West
This Key West cottage is located in the Historic District, just a short walk from Duval Street, the Key West Firehouse Museum, and the Florida Keys Beaches, making it easy to explore the city's vibrant attractions. It has received excellent user ratings, ensuring a comfortable and enjoyable stay. This 900-square-foot cottage offers two bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a private garden, a swimming pool, and a spa, providing everything you need for a relaxing and memorable vacation.
9.6 176 reviews
Key West, FL
07/02 – 07/07
$546/nighttotal: $2730 (5 )
Colony Poolside: A Charming Bungalow Near Duval Street
1 2
cottage , Key West
Colony Poolside is a one-bedroom bungalow located in Historic Old Town Key West, just a short walk from Duval Street and close to beaches, shopping, and restaurants. This cozy cottage has received excellent ratings for its location, cleanliness, and overall experience. The 550-square-foot bungalow comfortably sleeps two guests and features a spacious living area, a fully equipped kitchen, and a private deck with a grill. Enjoy a refreshing dip in the shared pool, relax in the garden, or take advantage of the spa, all within the peaceful private compound.
9.4 140 reviews
Key West, FL
06/20 – 06/27
$354/nighttotal: $2478 (7 )
Colony Calypso - A Quaint 1 Bedroom Cottage Just Two Blocks To Duval
1 2
cottage , Key West
Colony Calypso is a 1-bed 1-bath cottage with a private deck, located in the heart of Old Town Key West, just a short walk from Duval Street. The cottage is surrounded by lush tropical greenery and has excellent user and location ratings. With 530 square feet of living space, the cottage can accommodate up to 2 guests and features a fully equipped kitchen, a spacious bedroom with a king-size bed, and an open-concept living area. Guests can enjoy al fresco dining on the private deck, relax by the shared pool, or explore the nearby shops, restaurants, and nightlife.
9.8 118 reviews
Key West, FL
07/02 – 07/07
$487/nighttotal: $2435 (5 )
Colony Sunset- Bright And Airy Cottage In The Heart Of Old Town Key West
1 2
cottage , Key West
This charming Key West cottage is located in The Colony, a gated community just steps from Duval Street, offering a peaceful retreat while still being close to the action. Guests rave about the cottage's excellent rating, highlighting its comfortable and relaxing atmosphere. The cottage offers 530 square feet of living space, featuring one bedroom and one bathroom, comfortably accommodating up to four guests. Enjoy a private deck, a shared pool, and a fully equipped kitchen with a sit-down bar, perfect for enjoying meals and relaxing after a day of exploring Key West.
9.2 86 reviews
Key West, FL
08/22 – 08/29
$356/nighttotal: $2492 (7 )
Conch Republic Consul General's Cottage.-pool-historic District-assigned Parking
1 2
cottage , Key West
This charming Key West cottage is located in the Historic District, just a short walk from Duval Street, the Key West Firehouse Museum, and the Ernest Hemingway Home and Museum. It's also a quick walk to the beautiful Florida Keys Beaches, offering the perfect blend of peace and proximity to attractions. Guests consistently rate this vacation rental excellent, praising its convenience and comfortable amenities. The cottage features one bedroom and one bathroom, comfortably accommodating up to four guests. Relax and enjoy the Florida sunshine with the private outdoor pool, barbecue grills, and patio, or unwind in the spa. The fully equipped kitchen, free WiFi, and washing machine ensure a relaxing and convenient stay.
Our Favorite Family-Friendly Cottages in Key West, FL
Finding the perfect cottage makes all the difference for a comfortable and memorable family trip to Key West, FL.
8.4 7 reviews
Key West, FL
12/21 – 01/18
$515/nighttotal: $14420 (28 )
~Royal Poinciana Cottage~ Come And Indulge Yourself In Some Kw Sunshine!
1 1
cottage , Key West
This pet-friendly Key West cottage, located in Old Town, is a short walk from Saint Mary Star of the Sea Church and the Key West Firehouse Museum, offering easy access to beaches and attractions like the Ernest Hemingway Home and Museum. The one-bathroom rental boasts a fully equipped kitchen, in-unit laundry, air conditioning, Wi-Fi, a private porch, and access to a shared pool; it comfortably sleeps two guests and includes on-site barbecue facilities.
Best Key West, FL cottages with a garden
8.4 7 reviews
Key West, FL
12/21 – 01/18
$515/nighttotal: $14420 (28 )
~Royal Poinciana Cottage~ Come And Indulge Yourself In Some Kw Sunshine!
1 1
cottage , Key West
This pet-friendly Key West cottage, located in Old Town, is a short walk from Saint Mary Star of the Sea Church and the Key West Firehouse Museum, offering easy access to beaches and attractions like the Ernest Hemingway Home and Museum. The one-bathroom rental boasts a fully equipped kitchen, in-unit laundry, air conditioning, Wi-Fi, a private porch, and access to a shared pool; it comfortably sleeps two guests and includes on-site barbecue facilities.
9.6 394 reviews
Key West, FL
10/17 – 10/24
$829/nighttotal: $5803 (7 )
Pete's East Cottage: Cypress East Cottage Steps From Duval
1 2
cottage , Key West
This charming Key West cottage is located in Old Town, just a short walk from the Banana Cafe Restaurant and Coffee and Tea house, offering easy access to delicious food and drinks. The cottage boasts excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay. The cottage features a spacious living area with a spiral staircase leading to a loft bedroom, as well as a semi-private deck and lounge area for relaxation. Guests can enjoy the large kidney-shaped pool with a waterfall, a fully equipped kitchen, and the convenience of keyless entry.
9.6 176 reviews
Key West, FL
07/02 – 07/07
$546/nighttotal: $2730 (5 )
Colony Poolside: A Charming Bungalow Near Duval Street
1 2
cottage , Key West
Colony Poolside is a one-bedroom bungalow located in Historic Old Town Key West, just a short walk from Duval Street and close to beaches, shopping, and restaurants. This cozy cottage has received excellent ratings for its location, cleanliness, and overall experience. The 550-square-foot bungalow comfortably sleeps two guests and features a spacious living area, a fully equipped kitchen, and a private deck with a grill. Enjoy a refreshing dip in the shared pool, relax in the garden, or take advantage of the spa, all within the peaceful private compound.
9.4 140 reviews
Key West, FL
06/20 – 06/27
$354/nighttotal: $2478 (7 )
Colony Calypso - A Quaint 1 Bedroom Cottage Just Two Blocks To Duval
1 2
cottage , Key West
Colony Calypso is a 1-bed 1-bath cottage with a private deck, located in the heart of Old Town Key West, just a short walk from Duval Street. The cottage is surrounded by lush tropical greenery and has excellent user and location ratings. With 530 square feet of living space, the cottage can accommodate up to 2 guests and features a fully equipped kitchen, a spacious bedroom with a king-size bed, and an open-concept living area. Guests can enjoy al fresco dining on the private deck, relax by the shared pool, or explore the nearby shops, restaurants, and nightlife.
Frequently Asked Questions about cottages in Key West, FL
When is the best time to rent a cottage in Key West, FL?
The best time to visit Key West is during the shoulder seasons, from April to May or September to October, when the weather is still nice, but crowds are smaller and prices are lower.
You can't miss the Southernmost Point Buoy, the Hemingway House, and the Key West Lighthouse. Also, don't forget to walk along Duval Street and enjoy the lively atmosphere.
What are the best cottages with a pool in Key West, FL?
Why consider renting a cottage in Key West, FL for your stay?
Cottages offer a unique charm and a more intimate experience compared to hotels. They often come with a kitchen, allowing you to save money on meals. Many cottages also have private patios or balconies, perfect for relaxing after a day of exploring.
What are the best cottages with a jacuzzi in Key West, FL?
Can you easily explore Key West, FL on foot or by bike?
Absolutely! Key West is a very walkable city, and you can easily explore most of the main attractions on foot. Biking is also a popular option, especially for exploring the quieter neighborhoods and the scenic waterfront.
What are the best cottages for families and kids in Key West, FL?
What family-friendly activities are available in Key West, FL?
Key West has plenty of family-friendly activities, including the Key West Aquarium, the Butterfly Conservatory, and the Key West Shipwreck Treasure Museum. You can also take a guided tour of the historic Fort Zachary Taylor State Park or enjoy a relaxing day at Smathers Beach.
What are the best pet friendly cottages in Key West, FL?
Whether you prefer a jacuzzi or a hot tub, these Key West, FL cottages are designed for a private soak after a day by the water.
9.6 176 reviews
Key West, FL
07/02 – 07/07
$546/nighttotal: $2730 (5 )
Colony Poolside: A Charming Bungalow Near Duval Street
1 2
cottage , Key West
Colony Poolside is a one-bedroom bungalow located in Historic Old Town Key West, just a short walk from Duval Street and close to beaches, shopping, and restaurants. This cozy cottage has received excellent ratings for its location, cleanliness, and overall experience. The 550-square-foot bungalow comfortably sleeps two guests and features a spacious living area, a fully equipped kitchen, and a private deck with a grill. Enjoy a refreshing dip in the shared pool, relax in the garden, or take advantage of the spa, all within the peaceful private compound.
Neighborhoods and points of interest in Key West, FL
Explore Dog-Friendly Cottages in Key West, FL
A quality pet-friendly cottage in Key West, FL offers dog-friendly facilities for a stress-free stay near the water.
8.4 7 reviews
Key West, FL
12/21 – 01/18
$515/nighttotal: $14420 (28 )
~Royal Poinciana Cottage~ Come And Indulge Yourself In Some Kw Sunshine!
1 1
cottage , Key West
This pet-friendly Key West cottage, located in Old Town, is a short walk from Saint Mary Star of the Sea Church and the Key West Firehouse Museum, offering easy access to beaches and attractions like the Ernest Hemingway Home and Museum. The one-bathroom rental boasts a fully equipped kitchen, in-unit laundry, air conditioning, Wi-Fi, a private porch, and access to a shared pool; it comfortably sleeps two guests and includes on-site barbecue facilities.
9.8 118 reviews
Key West, FL
07/02 – 07/07
$487/nighttotal: $2435 (5 )
Colony Sunset- Bright And Airy Cottage In The Heart Of Old Town Key West
1 2
cottage , Key West
This charming Key West cottage is located in The Colony, a gated community just steps from Duval Street, offering a peaceful retreat while still being close to the action. Guests rave about the cottage's excellent rating, highlighting its comfortable and relaxing atmosphere. The cottage offers 530 square feet of living space, featuring one bedroom and one bathroom, comfortably accommodating up to four guests. Enjoy a private deck, a shared pool, and a fully equipped kitchen with a sit-down bar, perfect for enjoying meals and relaxing after a day of exploring Key West.