Key West, FL
2 2
$558/nighttotal: $2232 (4 )
Heart Of Downtown Key West Cottage With Off-street Parking
cottage - Key West
This charming Key West cottage is just a short walk from Duval Street, putting you in the heart of the action while still offering a peaceful retreat. It's received excellent ratings from previous guests, making it a popular choice for travelers. The home comfortably sleeps up to 3 guests in its two bedrooms. Enjoy amenities like a fully equipped kitchen, a private patio, and a spa, perfect for relaxing after a day exploring the island.
Key West, FL
4 2
$2758/nighttotal: $8274 (3 )
Pineapple Cottage - Top-rated Stay - Private Pool - 2bd/2.5bath
cottage - Key West
The Pineapple Cottage is located in Key West's Old Town district, just a short walk from Duval Street and its lively atmosphere. This cottage has consistently received excellent reviews from previous guests.
The cottage has two bedrooms and two bathrooms, comfortably accommodating up to five guests. Enjoy amenities like a private pool, a fully equipped kitchen, and a backyard oasis perfect for relaxing or grilling.
The cottage has two bedrooms and two bathrooms, comfortably accommodating up to five guests. Enjoy amenities like a private pool, a fully equipped kitchen, and a backyard oasis perfect for relaxing or grilling.
Key West, FL
2 1
$193/nighttotal: $16984 (88 )
Charming 1-bedroom Sleeps 2 Kitchenette In The Heart Of Key West-shared Pool
cottage - Key West
This Key West cottage, situated in New Town, offers convenient access to attractions like the Southernmost Point and Ernest Hemingway Home and Museum, with varying drive times depending on the specific location.
The one-bedroom unit features a queen bed, queen pull-out sofa, and twin rollaway bed, accommodating up to four guests and includes amenities such as air conditioning, Wi-Fi, and a jetted bathtub; nearby beaches and nature preserves provide additional recreational options.
The one-bedroom unit features a queen bed, queen pull-out sofa, and twin rollaway bed, accommodating up to four guests and includes amenities such as air conditioning, Wi-Fi, and a jetted bathtub; nearby beaches and nature preserves provide additional recreational options.
Key West, FL
2 1
$305/nighttotal: $1220 (4 )
Charming Deck And Inviting Living Space - Serene Coastal Retreat
cottage - Key West
Colony Poolside, a cottage within The Colony, is located in a secluded compound just steps from Duval Street, offering convenient access to award-winning restaurants, shopping, and beaches.
This family-friendly cottage accommodates up to 4 guests with 1 bedroom and 1 bathroom, featuring a private deck for grilling and al fresco dining, a fully equipped kitchen, air conditioning, and access to a shared swimming pool and a porch with Adirondack chairs.
This family-friendly cottage accommodates up to 4 guests with 1 bedroom and 1 bathroom, featuring a private deck for grilling and al fresco dining, a fully equipped kitchen, air conditioning, and access to a shared swimming pool and a porch with Adirondack chairs.
Key West, FL
2 2
$363/nighttotal: $2541 (7 )
Tropical Oasis With Swimming Pool And Outdoor Shower - Stunning Hideaway
cottage - Key West
This two-bedroom, two-bathroom Key West cottage, accommodating up to six guests, is situated in a private, gated enclave just two blocks from Higgs Beach and a short walk to local restaurants and the KW Butterfly & Nature Museum.
This 1,152 sq ft vacation rental offers a shared swimming pool with a grill and deck, air conditioning, internet, a full kitchen, and a private outdoor shower, with opportunities for stargazing and convenient access to island attractions.
This 1,152 sq ft vacation rental offers a shared swimming pool with a grill and deck, air conditioning, internet, a full kitchen, and a private outdoor shower, with opportunities for stargazing and convenient access to island attractions.
Key West, FL
2 3
$733/nighttotal: $64504 (88 )
Old Town Key West Cottage 3bed/2bath
cottage - Key West
This Key West cottage is located in the Historic District, a short walk from Duval Street and the Ernest Hemingway Home and Museum.
The three-bedroom, two-bathroom house sleeps nine guests and features a fully equipped kitchen with modern appliances, a private terrace, and access to a shared pool; on-site electric vehicle charging is available.
The three-bedroom, two-bathroom house sleeps nine guests and features a fully equipped kitchen with modern appliances, a private terrace, and access to a shared pool; on-site electric vehicle charging is available.
Key West, FL
4 2
$732/nighttotal: $2196 (3 )
~Gardenia Cottage~18+ Adult Only Cottage Near Duval St
cottage - Key West
This non-smoking cottage in Key West's Historic District offers ocean views and is a short walk to Duval Street and Donkey Milk House, placing you steps from Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park. This 2-bedroom, 1-bathroom abode accommodates up to 4 guests and features air conditioning, Wi-Fi, a microwave, and access to nearby water activities.
Key West, FL
2 2
$573/nighttotal: $2292 (4 )
Tropical Landscaping And Private Deck - Charming Coastal Escape
cottage - Key West
This 2-bedroom, 2-bathroom cottage in Key West is located among conch cottages with a private pond, offering a secluded setting within walking distance to Duval Street and Mallory Square.
This family-friendly accommodation sleeps up to 6 guests and features a full kitchen, air conditioning, a swimming pool, a spa, a tennis court, and a private deck with covered dining.
This family-friendly accommodation sleeps up to 6 guests and features a full kitchen, air conditioning, a swimming pool, a spa, a tennis court, and a private deck with covered dining.
Key West, FL
2 4
$761/nighttotal: $3044 (4 )
Charming Cottages With Pool And Tropical Breezes - Unique Retreat
cottage - Key West
This restored Key West shotgun home, featuring natural cypress exterior and clean lines, is located in a Key West district known for its iconic architecture and tropical atmosphere.
This family-friendly cottage accommodates up to 8 guests with 4 bedrooms and 2 bathrooms, offering amenities such as air conditioning, a full kitchen, a swimming pool with a waterfall, a spa, and a tennis court, with flexible rental options for the entire property or two separate twin cottages.
This family-friendly cottage accommodates up to 8 guests with 4 bedrooms and 2 bathrooms, offering amenities such as air conditioning, a full kitchen, a swimming pool with a waterfall, a spa, and a tennis court, with flexible rental options for the entire property or two separate twin cottages.
Key West, FL
2 1
$310/nighttotal: $1240 (4 )
~Margarita Cottage~ Bask In Sunshine And Lounge By Your Pool In Paradise.
cottage - Key West
Margarita Cottage, a Key West rental located in Historic Old Town, is within walking distance of Duval Street, Mallory Square, and El Siboney Cuban Restaurant.
This pet-friendly (one dog up to 25 lbs) one-bedroom cottage offers a private porch, outdoor grill, shared pool (seasonal heating available for a fee), and a fully equipped kitchen (microwave, refrigerator; no dishwasher) accommodating two guests.
This pet-friendly (one dog up to 25 lbs) one-bedroom cottage offers a private porch, outdoor grill, shared pool (seasonal heating available for a fee), and a fully equipped kitchen (microwave, refrigerator; no dishwasher) accommodating two guests.
Key West, FL
2 2
$331/nighttotal: $1324 (4 )
Kidney Shaped Pool And Semi-private Deck - Charming Tropical Haven
cottage - Key West
This restored Key West shotgun home, offering 2 bedrooms and 1 bathroom for up to 4 guests, is located just steps from Duval Street, providing direct access to dining and entertainment.
This rental features air conditioning, a full kitchen with a dishwasher, a swimming pool with a waterfall, a garden, a spa, and a tennis court, with an option to expand to a four bedroom/two bath configuration.
This rental features air conditioning, a full kitchen with a dishwasher, a swimming pool with a waterfall, a garden, a spa, and a tennis court, with an option to expand to a four bedroom/two bath configuration.
Key West, FL
2 1
$791/nighttotal: $1582 (2 )
New The Cottage At James House
cottage - Key West
The New Cottage at James House, a pet-friendly Key West rental, is located less than a mile from the city center, within walking distance of the Curry Mansion Museum, Mallory Dock, and the Waterfront Playhouse.
This one-bathroom Key West cottage sleeps two guests and offers free Wi-Fi, air conditioning, a microwave, and a refrigerator; contactless check-in/out is available.
This one-bathroom Key West cottage sleeps two guests and offers free Wi-Fi, air conditioning, a microwave, and a refrigerator; contactless check-in/out is available.
