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Summerland Key Vacation Rentals with Private Pool

(10 rentals)
Summerland Key House
Sleeps 10, 4 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atlantic. Sea Wall has room for (1) 24' boat. This home can sleep 7 adults and 2 small children. There are 4 bedrooms and 4-1/2 bath. Fully stocked modern kitchen, great out door space...

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$428
avg per night
Special Offer
Summerland Key House
Sleeps 9, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to the Lazy Lagoon, where stunning views emerge from just about everywhere on this property! Located in the very sought after “Summerland Cove” on Summerland Key, this home is situated at the end of Lagoon Drive with absolutely excellent open water access. Whether you are a fisherman,...

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$337
avg per night
Summerland Key House
Sleeps 14, 6 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Beautiful Ocean Front Home with six bedroom/Four bath. New memory foam mattresses in King and Queen rooms. Enjoy the heated pool, dock and beach. Located on Cudjoe Bay with panoramic view of the Atlantic and deep water swimming. Kayaks are provided for your enjoyment. There is a huge screened in porch...

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Featured review

"We would do it again!"

We enjoyed a family vacation for one week at this "villa". The view was spectacular and the interior spacious. There were plenty of spaces for all of us to sit and visit with each other. The pool was fun...

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$658
avg per night
New
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Casa Turquesa is the jewel of Summerland Key. Located directly on the beautiful crystal blue keys waters with deep water boat access for the avid angler and plenty of dockage for all the water toys.FLORIDA KEYS VACATION RENTALS! This stylish home is outfitted in Florida tropical style with cool and...

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$297
avg per night
New
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

“Endless Paradise” is truly a Cudjoe Gardens gem! This ground level (no stairs here!) vacation rental home is walk in and relax ready! Located in the highly desired Cudjoe Gardens neighborhood known for its great boating access, ground level prestigious builds, local marina and don’t...

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$350
avg per night

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New
Summerland Key House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The Shores of Sugarloaf Luxury Waterfront Home with Gorgeous Pool, Tiki Bar and SunsetsWelcome to the Shores of Sugarloaf, the perfect Florida Keys Island Getaway. Check-in to this gorgeous coastal home and enjoy a lovely vacation on one of the Florida Keys most desirable keys-Sugarloaf. This house...

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$495
avg per night
Summerland Key House
Sleeps 10, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The South House is a superb vacation home on Summerland Key. It offers everything you need to make your Florida Keys vacation truly memorable.The downstairs pool area is private and serene. There are several lounging areas to enjoy suntanning or wonderful afternoon shade. The crystal blue pool is...

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$385
avg per night
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This home is the ideal getaway for the whole family! The interior of the home is super spacious with an updated kitchen that looks out over the canal and large pool.There are three bedrooms, two bathrooms, and a large family area with a big screen television for your entertainment. Not to be outdone,...

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Featured review

"Outstanding location for fishing, boating, & diving!"

Stayed at this gem before and after Lobster mini season. The pool was perfectly refreshing after a day in the sun on the water. There are several free boat ramps nearby. Great proximity to the Looe key...

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$293
avg per night
Summerland Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beau Soleil is located in the most sought after neighborhood in the Lower Florida Keys, Summerland Cove, on Summerland Key. A gorgeous gem, tucked away in privacy with tropical plants and fruit trees everywhere you turn!This home is situated on a great boating canal with plenty of dockspace for your...

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$323
avg per night
Summerland Key House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Sea Noir Moments! A Lower Keys dream, located in the super popular upscale Summerland Cove neighborhood. This is not your average vacation rental, with a heated pool and spa, ample dockspace for your boat, and a giant screened in porch to enjoy your daily catch pest free! And that is just the outdoor...

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$383
avg per night
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