The 10 best cottages in Summerland Key, USA | Booking.com
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Cottages in Summerland Key

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Find the right cottage for you in Summerland Key

The best cottages in Summerland Key

Check out our pick of great cottages in Summerland Key

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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 Summerland Key and surroundings in the past month

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Travelling by car? These cottages in Summerland Key and nearby offer free parking

  • Unit 101

    Cudjoe Key
    Free parking

    Set in Cudjoe Key in the Florida region, Unit 101 features a balcony. This property offers access to a terrace, free private parking and free WiFi.

    From US$810.77 per night
  • Unit 101

    Cudjoe Key
    Free parking

    Situated in Cudjoe Key in the Florida region, Unit 101 features a balcony. This property offers access to a terrace, free private parking and free WiFi.

    From US$801.50 per night
  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 4 reviews

    Featuring air-conditioned accommodation with a private pool, pool view and a patio, Ocean View with Pool, 4 bedroom Vila Near Key West is located in Cudjoe Key.

  • Located in Big Pine Key, RV In The Keys a Tropical Retreat provides accommodation with private pool, free WiFi and free private parking for guests who drive.

    From US$317.28 per night
  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 2 reviews

    Set in Cudjoe Key, Turtle Cove Views by Last Key Realty provides accommodation with a heated pool.

  • Situated in Cudjoe Key, Tidewater Views by Last Key Realty offers a heated pool.

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 18 reviews

    Featuring sea views, NAUTILUS...ocean front cottage retreat ~ provides accommodation with a private beach area, pool with a view and a garden, around 37 km from Ernest Hemingway Home and Museum.

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 18 reviews

    37 km from Ernest Hemingway Home and Museum in Cudjoe Key, OCEANIA... Water front cottage retreat ~ offers accommodation with access to a sauna and hot tub.

Enjoy breakfast in Summerland Key and nearby

  • Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 5 reviews

    Set in Cudjoe Key, Island Oasis ~ YOUR Paradise Awaits! offers accommodation with a private pool, a balcony and sea views. A hot tub is available for guests.

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 21 reviews

    Set in Cudjoe Key, 37 km from Ernest Hemingway Home and Museum and 37 km from Duval Street, Pelican's Roost, Waterfront comfort at Venture Out offers a private beach area and air conditioning.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Set in Cudjoe Key, Mermaid Magic by Last Key Realty provides accommodation with a heated pool.

  • Paradise Found

    Key West
    Breakfast options

    Located in Key West, 37 km from Duval Street and 37 km from Southernmost Point, Paradise Found offers air conditioning.

  • Dock Holiday

    Cudjoe Key
    Breakfast options
    Scored out of 10, guest rating 7.1
    Good - What previous guests thought, 6 reviews

    Featuring air-conditioned accommodation with a heated pool, Dock Holiday is located in Cudjoe Key. A hot tub is available for guests. The property features a restaurant with an outdoor dining area.

  • Situated in Cudjoe Key, Dolphin Daydreams by Last Key Realty offers accommodation with a heated pool.

  • Boasting air-conditioned accommodation with a patio, Oceanview Retreat with 60ft Seawall is situated in Cudjoe Key.

    From US$1,052.26 per night
  • Serenity Now Seaside Escape - Brand New Build! is set in Cudjoe Key, 38 km from Ernest Hemingway Home and Museum, 38 km from Duval Street, as well as 38 km from Southernmost Point.

These cottages in Summerland Key and nearby have options with free cancellation

  • Tree Top Paradise

    Cudjoe Key
    Free cancellation options available
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 36 reviews

    Boasting air-conditioned accommodation with a private pool, quiet street view and a patio, Tree Top Paradise is set in Cudjoe Key.

  • Sea La Vie

    Cudjoe Key
    Free cancellation options available

    Set just 38 km from Southernmost Point, Sea La Vie provides accommodation in Cudjoe Key with access to massage services, a terrace, as well as an ATM.

  • Carefree on Cudjoe by Last Key Realty

    Cudjoe Key
    Free cancellation options available

    Situated in Cudjoe Key, Carefree on Cudjoe by Last Key Realty features accommodation with private pool, free WiFi and free private parking for guests who drive.

  • Tobago Stars

    Little Torch Key
    Free cancellation options available

    Featuring air-conditioned accommodation with a patio, Tobago Stars is located in Little Torch Key. Spa facilities is available for guests. The property has a restaurant with an outdoor dining area.

  • Hawkins Lookout

    Cudjoe Key
    Free cancellation options available

    Featuring air-conditioned accommodation with a balcony, Hawkins Lookout is set in Cudjoe Key. Guests can benefit from a patio and an outdoor fireplace.

  • L`archipel

    Key West
    Free cancellation options available

    Located in Key West, 44 km from Ernest Hemingway Home and Museum and 44 km from Duval Street, L`archipel offers air conditioning.

  • Sailfish Retreat

    Cudjoe Key
    Free cancellation options available

    Situated in Cudjoe Key, 39 km from Duval Street and 39 km from Southernmost Point, Sailfish Retreat offers air conditioning.

  • Parrotfish Pointe

    Cudjoe Key
    Free cancellation options available

    Boasting air-conditioned accommodation with a private pool, Parrotfish Pointe is set in Cudjoe Key. This beachfront property offers access to a balcony.

Cottages that guests love in Summerland Key

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  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 330 reviews
    Very cute cottage and beautiful location.
    Guest review by
    Kristian
    Young couple
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 330 reviews
    The bungalow was cozy, clean and comfortable
    Guest review by
    Zoila
    Young couple
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 330 reviews
    Beautiful bungalow
    Guest review by
    Marisa
    Young couple
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 330 reviews
    Super quiet and relaxing stay, cabin we stayed in had everything we needed and a really comfortable bed. We enjoyed hanging out in the inflatable loungers on the pond, free bicycles to use (though they certainly could do with some maintenance!(
    Guest review by
    corry
    Young couple
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 330 reviews
    We had a great stay here. The staff were all very friendly and helpful. The grounds were beautiful and very clean. Our bungalow was very cute and beautifully decorated.
    Guest review by
    Lisa
    Young couple
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 330 reviews
    The bungalow was comfortable
    Guest review by
    Deena
    Young couple
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 330 reviews
    The bungalow were clean and comfortable. The staff was friendly and helpful, they provided us an extra blanket.
    Guest review by
    Magalie
    Group
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 330 reviews
    This is a great place, it's thought of everything- kayaks, bikes, aquacabanas, hammocks, a spacious design between cabins, rvs and sites with surrounding water and wetlands. We were a couple in a beautiful cabin but could see it's great for families too. The pool was a highlight too!
    Guest review by
    annette
    Young couple
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 330 reviews
    We absolutely loved the location, and the bungalow was fantastic and so cute. Perfect for a couple. It was amazing! We loved it! The shower was amazing also! Everything was top notch! Would stay there again without hesitation!
    Guest review by
    Cindy
    Young couple
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 330 reviews
    Modern lodge, clean, good space, great shower and nice view.
    Guest review by
    FGutierrezA
    Young couple