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The best cottages in Key West

Check out our pick of great cottages in Key West

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Key West Villas, hotel in Key West

Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street. A heated pool, daily continental breakfast, and free WiFi are provided.

This place is exceptional, very clean, cozy and centrally located- just perfect for our stay in Key West. The hosts warmly welcomed us and were extremely friendly and helpful throughout our stay. On top of anything else we very much appreciated the availability of comfortable pool towels, a really good washing machine & dryer and much more little things that were even complimentary to our surprise. The pool and hot tub are very nice too and are open until 10pm. We can highly recommend this facility and will definitely return when coming back to Key West.
Scored 9.7
9.7
Rated exceptional
Exceptional
380 reviews
Price from
£404.57
1 night, 2 adults
Sky Loft in Key West, hotel in Key West

In the centre of Key West, located within a short distance of Simonton Street Beach and South Beach, Sky Loft in Key West offers free WiFi, air conditioning and household amenities such as a...

Location was great
Scored 9.3
9.3
Rated superb
Superb
12 reviews
Price from
£387.14
1 night, 2 adults
The Cozy Little Cottage, hotel in Key West

Situated in Key West, less than 1 km from Fort Zachary Taylor State Park Beach and a 18-minute walk from Higgs Beach, The Cozy Little Cottage provides accommodation with amenities such as free WiFi...

Location, facilities and coziness
Scored 9.3
9.3
Rated superb
Superb
12 reviews
Price from
£403.51
1 night, 2 adults
St Kitts - Downtown Waterfront Penthouse Pool Dock Parking, hotel in Key West

Boasting air-conditioned accommodation with a pool with a view, pool view and a patio, St Kitts - Downtown Waterfront Penthouse Pool Dock Parking is situated in Key West.

Spacious, fully equipped condo with a wonderful view. Everything is 10/10. 🥰
Scored 9.2
9.2
Rated superb
Superb
9 reviews
Price from
£1,285.89
1 night, 2 adults
St Thomas - Waterfront Penthouse sleeps 16 w Pool & Boat Dock, hotel in Key West

Boasting air-conditioned accommodation with a pool with a view, pool view and a patio, St Thomas - Waterfront Penthouse sleeps 16 w Pool & Boat Dock is set in Key West.

Incredible facilities great responsive host
Scored 9.6
9.6
Rated exceptional
Exceptional
8 reviews
Price from
£1,285.89
1 night, 2 adults
Keys Please!, hotel in Key West

Set in the centre of Key West, 300 metres from South Beach and 700 metres from Fort Zachary Taylor State Park Beach, Keys Please! offers free WiFi, a garden and air conditioning.

Scored 9.2
9.2
Rated superb
Superb
6 reviews
Price from
£865.20
1 night, 2 adults
The St Martin -Hot Tub & Pool, hotel in Key West

Boasting air-conditioned accommodation with a patio, The St Martin -Hot Tub & Pool is situated in Key West. Both free WiFi and parking on-site are accessible at the holiday home free of charge.

Tennis court nearby and decent pool
Scored 9.8
9.8
Rated exceptional
Exceptional
9 reviews
Price from
£429.20
1 night, 2 adults
The Exuma Cay -Pool View & Parking, hotel in Key West

Boasting air-conditioned accommodation with a patio, The Exuma Cay -Pool View & Parking is situated in Key West. Featuring a lift, this property also provides guests with an outdoor pool.

It is very spacious and well laid out.
Scored 9.3
9.3
Rated superb
Superb
22 reviews
Price from
£443.03
1 night, 2 adults
Rose Lane Villas, hotel in Key West

Located in Key West, Florida, these villas feature a heated outdoor swimming pool. They are adjacent to dining and shopping on Duval Street. and 1.8 km from the Southernmost Point.

Location was perfect.
Scored 8.6
8.6
Rated fabulous
Fabulous
299 reviews
Price from
£323.48
1 night, 2 adults
Grand Marina Suite -Waterfront Condo, hotel in Key West

Located in Key West, 9.1 km from Ernest Hemingway Home and Museum and 9.2 km from Duval Street, Grand Marina Suite -Waterfront Condo offers a garden and air conditioning.

...
Scored 8.7
8.7
Rated fabulous
Fabulous
105 reviews
Price from
£467.28
1 night, 2 adults
All cottages in Key West
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Cottages are perfect for travellers who enjoy feeling cosy and independent in the countryside. Usually small, traditionally built houses, cottages spread across one or two floors, making them great for families, or holidays with a little more privacy.

Most booked cottages in Key West this month

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Enjoy breakfast in Key West!

  • Key West Villas
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 380 reviews

    Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street. A heated pool, daily continental breakfast, and free WiFi are provided.

    Service room Happy hours Thank you for this nice days

  • The Cozy Little Cottage
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 12 reviews

    Situated in Key West, less than 1 km from Fort Zachary Taylor State Park Beach and a 18-minute walk from Higgs Beach, The Cozy Little Cottage provides accommodation with amenities such as free WiFi...

    Loved the decor and cleanliness; located close to main attractions; comfortable place to stay

  • Sunrise on the Atlantic
    Scored 9.4
    9.4
    Rated superb
    Superb
     · 8 reviews

    Located in Key West, 400 metres from Smathers Beach and 600 metres from Rest Beach, Sunrise on the Atlantic offers free WiFi and air conditioning. This holiday home also features a pool with a view.

    The available amenities were very nice. The property is well maintained and inviting.

  • Coral Hammock Poolside Home
    Scored 9.4
    9.4
    Rated superb
    Superb
     · 5 reviews

    Featuring air-conditioned accommodation with a heated pool, Coral Hammock Poolside Home is located in Key West. This property offers access to a balcony, free private parking and free WiFi.

  • Julia Whitehead Guest Suites
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 6 reviews

    In the centre of Key West, located within a short distance of Fort Zachary Taylor State Park Beach and South Beach, Julia Whitehead Guest Suites offers free WiFi, air conditioning and household...

  • St Kitts - Downtown Waterfront Penthouse Pool Dock Parking
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 9 reviews

    Boasting air-conditioned accommodation with a pool with a view, pool view and a patio, St Kitts - Downtown Waterfront Penthouse Pool Dock Parking is situated in Key West.

    El departamento, muy lindo y perfectamente equipado

  • St Thomas - Waterfront Penthouse sleeps 16 w Pool & Boat Dock
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 8 reviews

    Boasting air-conditioned accommodation with a pool with a view, pool view and a patio, St Thomas - Waterfront Penthouse sleeps 16 w Pool & Boat Dock is set in Key West.

  • St Croix - Downtown 4x4 Waterfront Penthouse Pool Dock Pet
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 5 reviews

    Boasting air-conditioned accommodation with a pool with a view, pool view and a patio, St Croix - Downtown 4x4 Waterfront Penthouse Pool Dock Pet is set in Key West.

These cottages in Key West have options with FREE cancellation

  • Keys Please!
    Free cancellation options available
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 6 reviews

    Set in the centre of Key West, 300 metres from South Beach and 700 metres from Fort Zachary Taylor State Park Beach, Keys Please! offers free WiFi, a garden and air conditioning.

  • Sky Loft in Key West
    Free cancellation options available
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 12 reviews

    In the centre of Key West, located within a short distance of Simonton Street Beach and South Beach, Sky Loft in Key West offers free WiFi, air conditioning and household amenities such as a...

    Great location. Very quiet and private but still close to Duval St. Blackout shades in bedroom made for excellent sleeping.

  • Grand Marina Suite -Waterfront Condo
    Free cancellation options available
    Scored 8.7
    8.7
    Rated fabulous
    Fabulous
     · 105 reviews

    Located in Key West, 9.1 km from Ernest Hemingway Home and Museum and 9.2 km from Duval Street, Grand Marina Suite -Waterfront Condo offers a garden and air conditioning.

    Me encantó la tranquilidad y lo lindo que estaba todo

  • Rose Lane Villas
    Free cancellation options available
    Scored 8.6
    8.6
    Rated fabulous
    Fabulous
     · 299 reviews

    Located in Key West, Florida, these villas feature a heated outdoor swimming pool. They are adjacent to dining and shopping on Duval Street. and 1.8 km from the Southernmost Point.

    clean. well equipped and the location was amazing.

  • New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool
    Scored 8.6
    8.6
    Rated fabulous
    Fabulous
     · 8 reviews

    Located in the centre of Key West, 600 metres from South Beach and 700 metres from Fort Zachary Taylor State Park Beach, New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool offers free WiFi...

  • The Barbados -Bright Condo w Pool
    Free cancellation options available
    Scored 8.3
    8.3
    Rated very good
    Very good
     · 57 reviews

    Set in Key West, 6.5 km from Southernmost Point and 7.3 km from Ernest Hemingway Home and Museum, The Barbados -Bright Condo w Pool offers air conditioning.

    We had a chance to stay in Key West for reasonable price

  • Sea Breeze -Great Location!
    Scored 8.4
    8.4
    Rated very good
    Very good
     · 11 reviews

    In the heart of Key West, set within a short distance of South Beach and Fort Zachary Taylor State Park Beach, Sea Breeze -Great Location!

    Great location and good size apartment in Key west

  • Casa Key West-Pool & Free Parking
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 14 reviews

    Right in the heart of Key West, situated within a short distance of South Beach and Fort Zachary Taylor State Park Beach, Casa Key West-Pool & Free Parking offers free WiFi, air conditioning and...

    Location, cleanliness. Never found pool though 😉

Travelling by car? These cottages in Key West offer free parking!

FAQ about cottages in Key West

Cottages that guests love in Key West

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  • Avg. price/night: £377.54
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 2,863 reviews
    It is a great cozy hotel in the main party street district - very charming using old houses - also the poot in the middle is great - the staff very friendly, parking available (big plus) - very big plus: real silverware and reusable hard plastic/porcelain for breakfast (that was a big plus from a European eye and differentiates it from most hotels or motels we have seen in US). Also the charm is great.
    Klaus
    Young couple
  • Scored 9.2
    9.2
    Rated superb
    Superb
     · 1,111 reviews
    Amazing historic location in the middle of the old town. Super tranquil environment with lots of orchids, flowers, palm trees in the garden. 4 nice pools and very beautifully restored rooms and cottages. Also good breakfast provided every morning and amazing hosts either great tips for trips, i.e. the sunset sailing boat cruise! Thanks to the great team at Simonton for making our stay so great.
    Benedikt
    Young couple
  • Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 946 reviews
    It’s a lovely, cosy, romantic little hotel. In the middle of Downtown Key west. The garden is an urban jungle, the breakfast was exactly what we were expecting. We had an amazing stay. Also the personal was very helpful regarding restaurants, parking and the neighbourhood. Would definitely recommend.
    Aiko
    Young couple
  • Avg. price/night: £454.13
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 512 reviews
    Very cozy and in a good location, close enough to enjoy Duval St. without being bothered by the noise of the nightlife ;D Chilling in the hot tub after walking the whole day was a nice plus. It wasn't hot, because it was late at night, but we didn't need it to be after the scorching temperatures of the day
    Desirée
    Group
  • Avg. price/night: £440.61
    Scored 8.7
    8.7
    Rated fabulous
    Fabulous
     · 945 reviews
    A very cozy hotel. Every room is a little bungalow - arranged around the pool. A lot of sights, bars, restaurants, etc. are close by. Free parking (although limited to 6 slots) was always available. Towels for the pool and beach (and even sunscreen) is available near the pool. The staff is really friendly and helpful. Everything was very clean.
    E
    Ellen
    Young couple
  • Avg. price/night: £762.29
    Scored 8.3
    8.3
    Rated very good
    Very good
     · 1,132 reviews
    Beautiful bungalows, very clean and cosy.
    Filip
    Young couple
  • Avg. price/night: £454.63
    Scored 7.4
    7.4
    Rated good
    Good
     · 2,254 reviews
    Very cozy cabin close to the swimming pool and with a good restaurant. Amazing sea food available! Easy to drive around and good place for drinks.
    Paulo
    Young couple
  • Avg. price/night: £762.29
    Scored 8.3
    8.3
    Rated very good
    Very good
     · 1,132 reviews
    The pictures don't show all the real size of the hotel. It is big but cosy. Many charming white bungalows and apartments. The locations is good, almost close to the turistic points.
    André Dias Barreto
    Family with young children
  • Avg. price/night: £535.16
    Scored 8.9
    8.9
    Rated fabulous
    Fabulous
     · 2,781 reviews
    Very cozy bungalow style apartments, great location, great pool! Very good value for the money.
    Stefan
    People with friends
  • Avg. price/night: £459.53
    Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 2,846 reviews
    lovely cottage, wonderfully decorated, quite, nice seating on private terrace, quiet, loved key west, pool and beach area
    Laura
    Group

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