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Key West, FL cottages
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110 Best cottages in Key West, FL

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.

Tropical Oasis With Swimming Pool And Outdoor Shower - Stunning Hideaway - Key West, FL
9.6 46 reviews

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.
Hidden Oasis 3 Blocks From Duval - Key West, FL
9.6 102 reviews

Hidden Oasis 3 Blocks From Duval

cottage, Key West
This Key West cottage is just a short walk from Duval Street and the Key West Cemetery, offering easy access to the island's main attractions. It's rated excellent by previous guests and is perfect for a relaxing getaway.
The cottage has one bedroom and one bathroom with a floor area of 510 square feet, comfortably accommodating up to four guests. It offers a full kitchen, laundry facilities, cable TV, a private patio with a barbecue area, and access to a shared pool.
Tropical Oasis With Freeform Pool And Hammock - Charming Retreat - Key West, FL
9.8 36 reviews

Tropical Oasis With Freeform Pool And Hammock - Charming Retreat

cottage, Key West
This two-bedroom Key West cottage is located in Old Town, five blocks from the White Street Art District and seven blocks from Duval Street and the Historic Seaport.
This family-friendly vacation rental accommodates up to four guests and features a private courtyard with a pool, an Ipe deck, a secluded hammock, and a retro-style kitchen.
Colony Calypso - Key West, FL
9.2 48 reviews

Colony Calypso

cottage, Key West
This Key West bungalow, part of The Colony, is located in Old Town, two blocks from Duval Street, offering an island hideaway.
This one-bedroom, one-bathroom cottage accommodates up to four guests and features a king-size bed, a full kitchen, air conditioning, and access to a shared swimming pool and garden.

Best Key West, FL cottages with a garden

~Robinson Crusoe Cottage~ Delight In Island Vibes In This Home With A Pool. - Key West, FL
9.8 10 reviews

~Robinson Crusoe Cottage~ Delight In Island Vibes In This Home With A Pool.

cottage, Key West
Robinson Crusoe Cottage, a one-bedroom Key West guesthouse in Old Town, offers easy walking or biking access to Duval Street and Mallory Square.
This pet-friendly (one dog up to 25 lbs) rental features a queen bed, pull-out sofa, updated kitchen with microwave and fridge, private rear entrance, shared pool (heating extra), outdoor grill, and accommodates up to four guests.
Summer Discounts-conch Republic Consul Cottage.-pool-historic District-parking - Key West, FL
9.2 89 reviews

Summer Discounts-conch Republic Consul Cottage.-pool-historic District-parking

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.

Frequently Asked Questions about cottages in Key West, FL

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Top-Rated Cottages with a Hot Tub 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.

Kidney Shaped Pool And Semi-private Deck - Charming Tropical Haven - Key West, FL
9.8 105 reviews

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.

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.

~Conch Cottages~ Enjoy Your Next Island Vacation With Friends Right Here! - Key West, FL
10 7 reviews

~Conch Cottages~ Enjoy Your Next Island Vacation With Friends Right Here!

cottage, Key West
Conch Cottages, in Key West's Old Town, are conveniently located within walking or biking distance of Duval Street and Mallory Square.
Robinson Crusoe Cottage, one of three private rentals, offers a one-bedroom, three-bathroom unit sleeping up to eight guests, featuring a full kitchen (no dishwasher), private porch, air conditioning, and access to a shared pool (November-April, fee applies).
New The Cottage At James House - Key West, FL
No reviews

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.
~Royal Poinciana Cottage~ Come And Indulge Yourself In Some Kw Sunshine! - Key West, FL
8.8 9 reviews

~Royal Poinciana Cottage~ Come And Indulge Yourself In Some Kw Sunshine!

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.
Get Your Island Stlye On! - Key West, FL
9.6 84 reviews

Get Your Island Stlye On!

cottage, Key West
This charming Key West cottage sits on Duval Street, just a short walk from the Ernest Hemingway House and Museum, placing you in the heart of the island's lively atmosphere. Guests consistently rate this property excellent, enjoying its prime location and comfortable amenities.
This one-bedroom, one-bathroom cottage offers 520 square feet of space, comfortably accommodating up to four guests. The cottage features a fully equipped kitchen, a private patio, air conditioning, Wi-Fi, and a washer and dryer, ensuring a relaxing and convenient stay.
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