The 10 best cottages in Summerland Key, US | 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 selection of great cottages in Summerland Key

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Island Oasis ~ YOUR Paradise Awaits!

Cudjoe Key (Near Summerland Key)

23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Island Oasis ~ YOUR Paradise Awaits! offers accommodations with access to a hot tub. Guests may go for a swim in the private pool.

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 5 reviews
Location 8.0
Price from
$250
1 night, 2 adults

Sugarloaf Key RV Resort & Cottages

Summerland Key

Sugarloaf Key RV Resort & Cottages provides air-conditioned accommodations in Summerland Key. Both free Wifi and parking on-site are accessible at the vacation home free of charge.

R
Rachael
From
United States
Loved the room and outdoor area. Great location. Quiet. Lots to do there. Big trash can which is always great ! Would stay again and tell people to stay there
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 321 reviews
Location 8.9

Pelican's Roost, Waterfront comfort at Venture Out

Cudjoe Key (Near Summerland Key)

Featuring free bikes, Pelican's Roost, Waterfront comfort at Venture Out provides accommodations in Cudjoe Key.

B
Bettinna
From
United States
Location, attention to detail, and soooo many amenities!
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 21 reviews
Location 9.3

NAUTILUS...ocean front cottage retreat ~

Cudjoe Key (Near Summerland Key)

Providing a garden, NAUTILUS...ocean front cottage retreat ~ features accommodations in Cudjoe Key.

E
Erin
From
United States
The location and house was amazing! Communication was great! Only suggestion is to update the master bedroom mattress and turn up the heat on the showers water, we like a HOT shower. thank you!
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 18 reviews
Location 9.9

OCEANIA... water front cottage retreat ~

Cudjoe Key (Near Summerland Key)

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

A
Angelo
From
United States
Location was great. Really enjoyed it
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 18 reviews
Location 9.2

Tree Top Paradise

Cudjoe Key (Near Summerland Key)

23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Tree Top Paradise provides accommodations with access to a spa center.

L
Lisa
From
United States
The location easy to get to several of the islands either direction. The amenities on the property. The pool, views, friendly visitors and residents, the store, and security, etc...all perfect
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 31 reviews
Location 9.5

Dock Holiday

Cudjoe Key (Near Summerland Key)

Dock Holiday offers accommodations in Cudjoe Key, 23 miles from Ernest Hemingway Home and Museum and 23 miles from Duval Street. The vacation home has access to a restaurant.

M
Mary
From
United States
Wonderful location. Exceptionally clean. Fully stocked. Peaceful community. Just all around an A+!
Scored out of 10, guest rating 7.1
Good - What previous guests thought, 6 reviews
Location 8.1
All cottages in Summerland Key

Looking for a cottage?

Cottages are perfect for travelers who enjoy feeling cozy and independent in the countryside. Usually small, traditionally built houses, cottages are spread across one or two floors – making them great for families or vacations with a little more privacy.

Most booked cottages in Summerland Key and surrounding area in the past month

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

  • Turtle Cove Views by Last Key Realty

    Cudjoe Key
    Free cancellation options available
    Scored out of 10, guest rating 8.5
    Very Good - What previous guests thought, 2 reviews

    23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Turtle Cove Views by Last Key Realty provides accommodations with access to a hot tub and spa facilities.

  • Tidewater Views by Last Key Realty

    Cudjoe Key
    Free cancellation options available

    23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Tidewater Views by Last Key Realty offers accommodations with access to a hot tub and spa facilities.

  • Island Oasis ~ YOUR Paradise Awaits!

    Cudjoe Key
    Free cancellation options available
    Scored out of 10, guest rating 7.4
    Good - What previous guests thought, 5 reviews

    23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Island Oasis ~ YOUR Paradise Awaits! offers accommodations with access to a hot tub. Guests may go for a swim in the private pool.

  • NAUTILUS...ocean front cottage retreat ~

    Cudjoe Key
    Free cancellation options available
    Scored out of 10, guest rating 9.2
    Wonderful - What previous guests thought, 18 reviews

    Providing a garden, NAUTILUS...ocean front cottage retreat ~ features accommodations in Cudjoe Key.

  • OCEANIA... water front cottage retreat ~

    Cudjoe Key
    Free cancellation options available
    Scored out of 10, guest rating 9.2
    Wonderful - What previous guests thought, 18 reviews

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

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

    Featuring free bikes, Pelican's Roost, Waterfront comfort at Venture Out provides accommodations in Cudjoe Key.

  • Mermaid Magic by Last Key Realty

    Cudjoe Key
    Free cancellation options available
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Mermaid Magic by Last Key Realty provides accommodations with access to a hot tub and spa facilities.

  • Paradise Found

    Key West
    Free cancellation options available

    Paradise Found offers accommodations in Key West, 23 miles from Southernmost Point and 23 miles from Key West Aquarium. The air-conditioned accommodation is 23 miles from Duval Street.

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

  • Oceanview Retreat with 60ft Seawall offers accommodations in Cudjoe Key, 23 miles from Ernest Hemingway Home and Museum and 24 miles from Duval Street.

    From $826.69 per night
  • 23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Serenity Now Seaside Escape - Brand New Build! offers accommodations with access to a hot tub.

  • Scored out of 10, guest rating 8.9
    Excellent - What previous guests thought, 31 reviews

    23 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Tree Top Paradise provides accommodations with access to a spa center.

  • Offering massage services, Sea La Vie offers accommodations in Cudjoe Key.

  • Carefree on Cudjoe by Last Key Realty is located in Cudjoe Key, just 23 miles from Ernest Hemingway Home and Museum and 23 miles from Duval Street.

  • Blackbeard Retreat is located in Little Torch Key, just 29 miles from Ernest Hemingway Home and Museum and 29 miles from Duval Street.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 4 reviews

    21 miles from Ernest Hemingway Home and Museum in Cudjoe Key, Ocean View with Pool, 4 bedroom Vila Near Key West offers accommodations with access to a fitness room.

    From $758.56 per night
  • Costa Vida by Last Key Realty is located in Cudjoe Key, just 21 miles from Ernest Hemingway Home and Museum and 21 miles from Duval Street.

Enjoy breakfast in Summerland Key and nearby

  • Dock Holiday

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

    Dock Holiday offers accommodations in Cudjoe Key, 23 miles from Ernest Hemingway Home and Museum and 23 miles from Duval Street. The vacation home has access to a restaurant.

  • The vacation home has access to a restaurant. The vacation home also offers facilities for disabled guests.

  • Hawkins Lookout

    Cudjoe Key
    Breakfast options

    Hawkins Lookout is located in Cudjoe Key, just 24 miles from Ernest Hemingway Home and Museum and 24 miles from Duval Street. Guests can benefit from a patio and an outdoor fireplace.

  • L`archipel

    Key West
    Breakfast options

    L`archipel is located in Key West, just 27 miles from Duval Street and 28 miles from Southernmost Point. The air-conditioned accommodation is 27 miles from Ernest Hemingway Home and Museum.

  • Sailfish Retreat is located in Cudjoe Key, just 24 miles from Southernmost Point and 24 miles from Key West Aquarium. The air-conditioned accommodation is 24 miles from Duval Street.

  • Parrotfish Pointe is located in Cudjoe Key, just 24 miles from Ernest Hemingway Home and Museum and 24 miles from Duval Street. This beachfront property offers access to a patio.

  • Cayo Loco

    Little Torch Key
    Breakfast options

    Cayo Loco is located in Little Torch Key, just 25 miles from Florida Keys Aquarium Encounters and 29 miles from Ernest Hemingway Home and Museum. The vacation home has access to a restaurant.

  • Foster`s Folly

    Key West
    Breakfast options

    Foster`s Folly is located in Key West, just 30 miles from Duval Street and 30 miles from Southernmost Point. The air-conditioned accommodation is 30 miles from Ernest Hemingway Home and Museum.

Cottages That Guests Love in Summerland Key

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  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 321 reviews
    Very cute cottage and beautiful location.
    Guest review by
    Kristian
    Young couple
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 321 reviews
    The bungalow was cozy, clean and comfortable
    Guest review by
    Zoila
    Young couple
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 321 reviews
    Beautiful bungalow
    Guest review by
    Marisa
    Young couple
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 321 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
    Wonderful - What previous guests thought, 321 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
    Wonderful - What previous guests thought, 321 reviews
    The bungalow was comfortable
    Guest review by
    Deena
    Young couple
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 321 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
    Wonderful - What previous guests thought, 321 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
    Wonderful - What previous guests thought, 321 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
    Wonderful - What previous guests thought, 321 reviews
    Modern lodge, clean, good space, great shower and nice view.
    Guest review by
    FGutierrezA
    Young couple