~Robinson Crusoe Cottage~ Delight In Island Vibes In This Home With A Pool.
1 2
cottage , Key West
Robinson Crusoe Cottage, a one-bedroom Key West holiday home in Old Town, is within walking or cycling distance of Duval Street and Mallory Square. This self-catering property sleeps four, offering a queen bed, pull-out sofa bed, updated kitchen with appliances, a private rear entrance, shared pool (heating at extra cost), and outdoor grill; one dog (up to 11kg) is permitted (fees apply).
9.2 86 reviews
Key West, FL
11/07 – 18/07
£233/nighttotal: £1631 (7 )
Summer Discounts-conch Republic Consul Cottage.-pool-historic District-parking
1 4
cottage , Key West
This charming cottage is located in the heart of Key West's Historic District, just a kilometre from the Key West Firehouse Museum and Duval Street, and within a 1.5 kilometre walk of the Florida Keys Beaches and the Ernest Hemingway Home and Museum. It has been rated excellent by previous guests. The cottage has one bedroom and one bathroom and can accommodate up to four guests. Amenities include a swimming pool, a terrace, a garden, and free Wi-Fi, as well as a fully equipped kitchen, a washing machine, and a coffee maker.
9.8 118 reviews
Key West, FL
20/07 – 27/07
£328/nighttotal: £2296 (7 )
Colony Sunset- Bright And Airy Cottage In The Heart Of Old Town Key West
1 1
cottage , Key West
This charming cottage is situated in The Colony, a peaceful gated community just a short walk from the lively Duval Street in Key West. The cottage boasts excellent user ratings and is a popular choice for travellers seeking a relaxing escape. The cottage offers 49 square metres of living space and comfortably accommodates four guests. The cottage features a private deck, a shared swimming pool, a well-equipped kitchen, and a spa, ensuring a comfortable and enjoyable stay.
9.2 21 reviews
Key West, FL
28/06 – 02/07
£538/nighttotal: £2152 (4 )
Find Your Zen At Hidden Treasure
2 4
cottage , Key West
This charming Key West cottage is ideally situated just a short walk from Duval Street and the Key West Cemetery, offering easy access to the island's vibrant nightlife and historic attractions. The surrounding area is known for its relaxed atmosphere and proximity to the waterfront. This two-bedroom, two-bathroom property spans 64 square metres and comfortably accommodates up to six guests. The cottage features a fully equipped kitchen, air conditioning, a shared pool, a garden, a barbecue area, and free Wi-Fi, making it a perfect choice for families or groups seeking a relaxing and convenient stay.
Key West, FL
01/10 – 01/11
£235/nighttotal: £7285 (31 )
Quaint Key West Escape Old Town - Local Living
1 2
cottage , Key West
This one-bedroom holiday home is located in Old Town Key West, a short walk from Duval Street and near the Ernest Hemingway Home and Museum and Southernmost Point. This accommodation, suitable for up to three guests, offers air conditioning, a private patio surrounded by tropical landscaping, and a remodelled interior with French doors, all within easy reach of Fort Zachary Taylor Historic State Park.
10 238 reviews
Key West, FL
28/06 – 02/07
£533/nighttotal: £2132 (4 )
Pineapple Cottage - Top-rated Stay - Private Pool - 2bd/2.5bath
2 4
cottage , Key West
The Pineapple Cottage is located in Old Town, Key West, just half a block from Duval Street, putting you right in the heart of the action. The cottage has excellent user ratings and offers a comfortable and convenient stay. The cottage has two bedrooms and two bathrooms, accommodating up to five guests. It boasts a private pool and backyard oasis, a fully equipped kitchen, and a range of entertainment options, ensuring a relaxing and enjoyable stay.
9.4 140 reviews
Key West, FL
13/09 – 27/09
£225/nighttotal: £3150 (14 )
Colony Calypso - A Quaint 1 Bedroom Cottage Just Two Blocks To Duval
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cottage , Key West
Colony Calypso is a one-bedroom bungalow in Old Town Key West, just 0.3 km from Duval Street and its lively atmosphere. The cottage has received excellent ratings for location, cleanliness and user experience. The bungalow is 49 square metres and comfortably sleeps two guests. Guests can enjoy a private deck with a gas grill, a shared swimming pool, and access to a spa.
9.6 176 reviews
Key West, FL
27/06 – 04/07
£341/nighttotal: £2387 (7 )
Colony Poolside: A Charming Bungalow Near Duval Street
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cottage , Key West
Colony Poolside is a one-bedroom bungalow situated in the historic Old Town district of Key West, just a short walk from Duval Street and a few kilometres from the beach. The property has received excellent ratings for its location, cleanliness, and overall experience. The bungalow is 51 square metres and can accommodate two guests. It has a fully equipped kitchen, a private deck, a shared pool, and a garden, offering everything you need for a relaxing and enjoyable stay.
9.4 172 reviews
Key West, FL
22/08 – 29/08
£270/nighttotal: £1890 (7 )
Conch Republic Consul General's Cottage.-historic District
2 2
cottage , Key West
This charming cottage is located in the Key West Historic District, just under a kilometre from Duval Street and the Key West Firehouse Museum, and within a 1.5 kilometre walk of the Florida Keys Beaches and the Ernest Hemingway Home and Museum. This property has received excellent guest reviews. The cottage, which spans 84 square metres, comfortably accommodates up to six guests in two bedrooms and two bathrooms. The property offers a range of amenities including a fully equipped kitchen, a swimming pool, a garden, a spa, and parking.
9.6 100 reviews
Key West, FL
30/10 – 04/11
£421/nighttotal: £2105 (5 )
Hidden Oasis 3 Blocks From Duval
1 2
cottage , Key West
This charming cottage is situated just a short walk from Duval Street, Key West Cemetery, and the waterfront, offering easy access to the island's vibrant attractions and the beautiful ocean. It has received excellent reviews from previous guests, highlighting its convenient location and comfortable amenities. The cottage spans 47 square meters and comfortably accommodates up to four guests in one bedroom and one bathroom. It features a private terrace, shared pool access, a barbecue area, a fully equipped kitchen, laundry facilities, and parking, ensuring a relaxing and enjoyable stay.
10 80 reviews
Key West, FL
27/06 – 04/07
£455/nighttotal: £3185 (7 )
"Tranquility " At Ann Street Gardens Steps From Duval
1 2
cottage , Key West
This charming one-bedroom cottage is situated in the heart of Key West's Historic District, just a short walk from Mallory Square, the Historic Seaport, and Duval Street's lively bars and restaurants. Guests have consistently rated this property as excellent, highlighting its peaceful atmosphere and convenient location. The cottage offers a private courtyard with a deck and outdoor furniture, perfect for enjoying the warm Key West weather. It also features a shared pool and garden, a fully equipped kitchen, air conditioning, and a spa-like bathroom with a walk-in shower.
9.8 6 reviews
Key West, FL
29/12 – 27/01
£769/nighttotal: £22301 (29 )
Tranquility - Tucked Away In The Meadows - Private Pool - 3bd/3bath
3 2
cottage , Key West
Tranquility Cottage is located in Key West's Historic District, seven blocks (approximately 0.6 km) from Duval Street, offering easy access to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park. This three-bedroom, three-bathroom holiday home boasts 122 square metres of living space, comfortably accommodating six guests and featuring a private pool, fully equipped kitchen, free Wi-Fi, and on-street parking; monthly rentals are available.
Guest-Favourite Family-Friendly Cottages in Key West, FL
Family-friendly cottages near the Key West, FL coast provide ample space and easy access to local beaches.
9.6 100 reviews
Key West, FL
30/10 – 04/11
£421/nighttotal: £2105 (5 )
Hidden Oasis 3 Blocks From Duval
1 2
cottage , Key West
This charming cottage is situated just a short walk from Duval Street, Key West Cemetery, and the waterfront, offering easy access to the island's vibrant attractions and the beautiful ocean. It has received excellent reviews from previous guests, highlighting its convenient location and comfortable amenities. The cottage spans 47 square meters and comfortably accommodates up to four guests in one bedroom and one bathroom. It features a private terrace, shared pool access, a barbecue area, a fully equipped kitchen, laundry facilities, and parking, ensuring a relaxing and enjoyable stay.
Best Key West, FL cottages with a garden
9.6 84 reviews
Key West, FL
11/07 – 18/07
£364/nighttotal: £2548 (7 )
Get Your Island Stlye On!
1 4
cottage , Key West
This charming cottage is located on Duval Street, just a short walk from the Ernest Hemingway House and Museum and Fort Zachary Taylor Historic State Park, placing you in the heart of Key West's lively atmosphere. This property has received excellent reviews from previous guests. The cottage offers 48 square metres of space, comfortably accommodating up to four guests, and features a well-equipped kitchen, a private patio, and a laundry facility. Guests can also enjoy the use of a barbecue area, a spa, and parking on site.
9.5 117 reviews
Key West, FL
11/07 – 18/07
£1003/nighttotal: £7021 (7 )
Havana Lane: An Updated Classic Conch Cottage With Still A Rustic Edge!
1 4
cottage , Key West
This charming cottage is located in Old Town Key West, just a short walk from the White Street Art District and a 1.1 km walk or cycle ride from Duval Street and the Historic Seaport. The cottage enjoys an excellent user rating, location rating, and cleanliness rating, indicating a high standard of accommodation and service. The cottage spans 95 square metres and comfortably sleeps up to four guests in its two bedrooms and two bathrooms. The property offers a range of amenities and features, including a private courtyard with a swimming pool, a fully equipped kitchen, air conditioning, Wi-Fi, a terrace, a garden, a spa, parking, and a relaxing outdoor living area.
8.4 7 reviews
Key West, FL
29/12 – 27/01
£377/nighttotal: £10933 (29 )
~Royal Poinciana Cottage~ Come And Indulge Yourself In Some Kw Sunshine!
1 2
cottage , Key West
This pet-friendly Key West cottage is located in Old Town, a short walk from St Mary Star of the Sea Church and the Key West Firehouse Museum, offering easy access to the ocean. The self-catering property sleeps two guests and features a fully equipped kitchen, air conditioning, a private porch, shared pool, in-unit laundry, and Wi-Fi; nearby attractions include the Southernmost Point and the Ernest Hemingway Home and Museum.
Frequently asked questions about cottages in Key West, FL
What would be a good 2-days itinerary for visiting Key West, FL?
On your first day, visit the Southernmost Point of the Continental US and walk down Duval Street to see the shops and bars. In the evening, enjoy a sunset cruise or a meal at a restaurant with a view of the water. On your second day, explore the Key West Butterfly and Nature Conservatory and take a stroll through the historic Old Town district. You can also take a boat trip to see the dolphins and other marine life.
What part of Key West, FL is ideal for renting a cottage?
The Old Town area is the heart of Key West, offering a mix of historic architecture, vibrant nightlife, and excellent restaurants. It's a great location for a cottage rental, putting you within walking distance of many attractions. Alternatively, the quieter neighbourhood of New Town is also a good choice for a cottage rental, especially if you prefer a more relaxed atmosphere.
What are the best cottages with a pool 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 and September to October, when the weather is still pleasant but the crowds are smaller. You'll find better deals on cottage rentals during these months compared to the peak season, which runs from December to April.
What are the best cottages with a jacuzzi in Key West, FL?
You absolutely must see the Southernmost Point Buoy, a popular spot for photos. The Ernest Hemingway Home and Museum is a must-visit, and the Key West Aquarium is a great place to learn about the local marine life. If you're looking for some history, head to Fort Zachary Taylor State Park, a historic fort with stunning views of the water.
What are the best cottages for families and kids in Key West, FL?
Why consider renting a cottage in Key West, FL for your stay?
Renting a cottage in Key West offers a more unique and intimate experience compared to staying in a hotel. You'll have more space and privacy, and you'll often find charming and characterful cottages with beautiful gardens. Many cottages also have kitchens, which can be convenient for preparing meals.
What are the best pet friendly cottages in Key West, FL?
Can you easily explore Key West, FL on foot or by bike?
Key West is a very walkable city, and many of the main attractions are within easy reach of each other. You can also easily rent a bike to explore the island at your own pace. There are dedicated bike paths and lanes throughout the city, making it a safe and enjoyable way to get around.
What are the best cottages with parking in Key West, FL?
What are the best restaurants in Key West, FL with nature views?
For stunning views of the ocean, try the Sunset Pier at the Ocean Key Resort or the Latitude 24 Restaurant. For a more casual dining experience with a view of the harbour, head to the Waterfront Brewery. Each offers a unique experience with delicious food and breathtaking views.
What family-friendly activities are available in Key West, FL?
Key West is a great place to visit with children. The Key West Aquarium is a popular choice for families, and the Key West Butterfly and Nature Conservatory is another great option. You can also take a sunset cruise with the kids, or visit the Key West Historic Seaport, where you can see historic ships and learn about the island's maritime heritage.
Destinations nearby
Handpicked Holiday Cottages with a Jacuzzi in Key West, FL
Unwind after a coastal adventure with a private hot tub soak at your Key West, FL cottage.
9.8 6 reviews
Key West, FL
29/12 – 27/01
£769/nighttotal: £22301 (29 )
Tranquility - Tucked Away In The Meadows - Private Pool - 3bd/3bath
3 2
cottage , Key West
Tranquility Cottage is located in Key West's Historic District, seven blocks (approximately 0.6 km) from Duval Street, offering easy access to the Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park. This three-bedroom, three-bathroom holiday home boasts 122 square metres of living space, comfortably accommodating six guests and featuring a private pool, fully equipped kitchen, free Wi-Fi, and on-street parking; monthly rentals are available.
Browse Pet-Friendly Cottages in Key West, FL
Secure a dog-friendly cottage in Key West, FL featuring outdoor washing stations and proximity to the shoreline.
9.6 100 reviews
Key West, FL
30/10 – 04/11
£421/nighttotal: £2105 (5 )
Hidden Oasis 3 Blocks From Duval
1 2
cottage , Key West
This charming cottage is situated just a short walk from Duval Street, Key West Cemetery, and the waterfront, offering easy access to the island's vibrant attractions and the beautiful ocean. It has received excellent reviews from previous guests, highlighting its convenient location and comfortable amenities. The cottage spans 47 square meters and comfortably accommodates up to four guests in one bedroom and one bathroom. It features a private terrace, shared pool access, a barbecue area, a fully equipped kitchen, laundry facilities, and parking, ensuring a relaxing and enjoyable stay.
8.4 7 reviews
Key West, FL
29/12 – 27/01
£377/nighttotal: £10933 (29 )
~Royal Poinciana Cottage~ Come And Indulge Yourself In Some Kw Sunshine!
1 2
cottage , Key West
This pet-friendly Key West cottage is located in Old Town, a short walk from St Mary Star of the Sea Church and the Key West Firehouse Museum, offering easy access to the ocean. The self-catering property sleeps two guests and features a fully equipped kitchen, air conditioning, a private porch, shared pool, in-unit laundry, and Wi-Fi; nearby attractions include the Southernmost Point and the Ernest Hemingway Home and Museum.
10 7 reviews
Key West, FL
30/10 – 04/11
£426/nighttotal: £2130 (5 )
~Robinson Crusoe Cottage~ Delight In Island Vibes In This Home With A Pool.
1 2
cottage , Key West
Robinson Crusoe Cottage, a one-bedroom Key West holiday home in Old Town, is within walking or cycling distance of Duval Street and Mallory Square. This self-catering property sleeps four, offering a queen bed, pull-out sofa bed, updated kitchen with appliances, a private rear entrance, shared pool (heating at extra cost), and outdoor grill; one dog (up to 11kg) is permitted (fees apply).
9.2 21 reviews
Key West, FL
28/06 – 02/07
£538/nighttotal: £2152 (4 )
Find Your Zen At Hidden Treasure
2 4
cottage , Key West
This charming Key West cottage is ideally situated just a short walk from Duval Street and the Key West Cemetery, offering easy access to the island's vibrant nightlife and historic attractions. The surrounding area is known for its relaxed atmosphere and proximity to the waterfront. This two-bedroom, two-bathroom property spans 64 square metres and comfortably accommodates up to six guests. The cottage features a fully equipped kitchen, air conditioning, a shared pool, a garden, a barbecue area, and free Wi-Fi, making it a perfect choice for families or groups seeking a relaxing and convenient stay.
Search Cottages by the Shore in Key West, FL
Plan an amazing coastal holiday at comfortable shoreside cottages in Key West, FL close to the shore.
9.4 172 reviews
Key West, FL
22/08 – 29/08
£270/nighttotal: £1890 (7 )
Conch Republic Consul General's Cottage.-historic District
2 2
cottage , Key West
Compare Luxury Cottages in Key West, FL
These luxury coastal cottages in Key West, FL set a refined tone for your high-end seaside holiday.
9.5 117 reviews
Key West, FL
11/07 – 18/07
£1003/nighttotal: £7021 (7 )
Havana Lane: An Updated Classic Conch Cottage With Still A Rustic Edge!
1 4
cottage , Key West
Top-Rated Holiday Cottages with a Swimming Pool in Key West, FL
These cottages in Key West, FL feature swimming pools, perfect for a dip right alongside the local sands.
9.2 86 reviews
Key West, FL
11/07 – 18/07
£233/nighttotal: £1631 (7 )
Summer Discounts-conch Republic Consul Cottage.-pool-historic District-parking
1 4
cottage , Key West
Choose the Right Holiday Cottages with Free Parking in Key West, FL
Forget parking stress with free on-site spaces included at these waterside cottages in Key West, FL.
10 238 reviews
Key West, FL
28/06 – 02/07
£533/nighttotal: £2132 (4 )
Pineapple Cottage - Top-rated Stay - Private Pool - 2bd/2.5bath
2 4
cottage , Key West
Search Holiday Cottages with Spa Facilities in Key West, FL
Choose a cottage with a spa in Key West, FL for effortless waterside wellness during your coastal break.