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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Island Oasis ~ YOUR Paradise Awaits!

Cudjoe Key (Near Summerland Key)

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.

A
Ani
From
Croatia
Good location, close to Key West and other attractions across the Keys. Quiet neighborhood. Helpful hosts and receptionists. Very cozy place, with a nice terrace, lovely view, comfortable rooms and well-equipped. We enjoyed our stay.
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 6 reviews
Price from
£211.02
1 night, 2 adults

Sugarloaf Key RV Resort & Cottages

Summerland Key

Situated in Summerland Key, 32 km from Ernest Hemingway Home and Museum, Sugarloaf Key RV Resort & Cottages features air-conditioned rooms with free WiFi.

N
Neisa
From
United States
Everything was perfect, very friendly staff, they even invited us for burgers 😀😀
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 315 reviews

Pelican's Roost, Waterfront comfort at Venture Out

Cudjoe Key (Near Summerland Key)

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 9.1
Superb - What previous guests thought, 20 reviews

NAUTILUS...ocean front cottage retreat ~

Cudjoe Key (Near Summerland Key)

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

OCEANIA... water front cottage retreat ~

Cudjoe Key (Near Summerland Key)

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.

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

Tree Top Paradise

Cudjoe Key (Near Summerland Key)

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

A
Amanda
From
United States
The screened in porch was lovely! The whole place was beautifully decorated and comfortable. The palm trees and palms were surrounding the house and it was so nice. Would definitely stay here again!
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 30 reviews

Dock Holiday

Cudjoe Key (Near Summerland Key)

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.

K
Kris Thomas Booking.com
From
United States
The location was behind a 24 hour security gate with someone at the gate 27/7. Our unit was clean and right on the a canal. It had a full kitchen stocked with all the pots, pans, and silverware you would ever need. The unit had dishwasher, washing machine and dryer. The larger property complex our unit was in had beach access, a pool and laundry facilities.
Scored out of 10, guest rating 7.1
Good - What previous guests thought, 6 reviews
All cottages in Summerland Key

Looking for a cottage?

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

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

  • 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.

  • 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.

  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 20 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.

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

  • Island Oasis ~ YOUR Paradise Awaits!

    Cudjoe Key
    Free cancellation options available
    Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 6 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.

  • Paradise Found

    Key West
    Free cancellation options available

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

  • Blackbeard`s Hideaway

    Key West
    Free cancellation options available

    Offering sea views, Blackbeard`s Hideaway is an accommodation situated in Key West, 37 km from Duval Street and 37 km from Southernmost Point.

  • Dock Holiday

    Cudjoe Key
    Free cancellation options available
    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.

  • 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.

  • Tree Top Paradise

    Cudjoe Key
    Free cancellation options available
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 30 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.

Enjoy breakfast in Summerland Key and nearby

  • Hawkins Lookout

    Cudjoe Key
    Breakfast options

    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
    Breakfast options

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

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

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

  • Cayo Loco

    Little Torch Key
    Breakfast options

    Featuring air-conditioned accommodation with a terrace, Cayo Loco is located in Little Torch Key. Guests staying at this holiday home have access to a balcony.

  • Foster`s Folly

    Key West
    Breakfast options

    Set in Key West, 42 km from Florida Keys Aquarium Encounters and 48 km from Ernest Hemingway Home and Museum, Foster`s Folly offers air conditioning.

  • Boasting air-conditioned accommodation with a balcony, Salty Air Retreat is situated in Little Torch Key. This holiday home also has a private pool.

  • Set in Cudjoe Key, Costa Vida by Last Key Realty offers accommodation with private pool, free WiFi and free private parking for guests who drive.

Cottages that guests love in Summerland Key

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  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 315 reviews
    Very cute cottage and beautiful location.
    Guest review by
    Kristian
    Young couple
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 315 reviews
    The bungalow was cozy, clean and comfortable
    Guest review by
    Zoila
    Young couple
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 315 reviews
    Beautiful bungalow
    Guest review by
    Marisa
    Young couple
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 315 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 9.0
    Superb - What previous guests thought, 315 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 9.0
    Superb - What previous guests thought, 315 reviews
    The bungalow was comfortable
    Guest review by
    Deena
    Young couple
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 315 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 9.0
    Superb - What previous guests thought, 315 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 9.0
    Superb - What previous guests thought, 315 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 9.0
    Superb - What previous guests thought, 315 reviews
    Modern lodge, clean, good space, great shower and nice view.
    Guest review by
    FGutierrezA
    Young couple