Summerland Key Vacation Rentals with Private Pool

(5 rentals)
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Summerland Breeze - A Resort Style Three House Retreat

$950

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pets allowed
  • Private pool

About this property

Minimum 28-day rental.Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property....two cottages (each two-bedroom) and a main house overlooking the ocean. Located between the houses is a breathtaking resort-style pool, diving pool, and ...

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Property Type

Summerland Key House

"Peaceful and beautiful"
Reviewed October 21, 2021

The location is fabulous, you can sit under the tiki hut by the water and just take in the gorgeous views. Pool was awesome. It was only a short drive to Key West where you can walk Duval street and take ...

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Hogfish Hideout - New Swimming Pool

$233

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Welcome to the cleanest blue water flow-thru canal in the Keys! This comfortable home is clean and conveniently located at MM 24.5 on Summerland Key, near the beginning of a deep blue water canal.This elevated CBS home has concrete floors covered in ceramic tile and carpet in the bedrooms. The ...

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Property Type

Summerland Key House

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Isle Be Back

4 BR | 2 BA | Sleeps 8 | Quick View

$262

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pets allowed
  • Private pool

About this property

Spend your next vacation relaxing in the tropical splendor of this upscale, canal front home, appropriately know as Isle Be Back. Located in the desirable neighborhood of Summerland Key Cove, this spacious multi-story home offers the master bedroom and en suite bath o the uppermost floor with an adjacent ...

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Property Type

Summerland Key House

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REEL PARADISE

3 BR | 2 BA | Sleeps 6 | Quick View

$247

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool

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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Property Type

Summerland Key House

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Keys Life

3 BR | 3 BA | Sleeps 8 | Quick View

2

$194

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pets allowed
  • Private pool

About this property

Keys Life Come on down to “Keys Life” and enjoy a great Florida Keys vacation. Located in one of the best deep-water boating areas. The crystal blue canals and superb deep-water boating will make your fishing days a dream. Great outside entertaining areas with a perfect pool to splash around ...

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Property Type

Summerland Key House

"Incredible Patio & Pool space"
Reviewed July 9, 2021

The home was great but we most enjoyed about our stay was the spacious seating and dining area downstairs. There are several loungers and patio sets an awesome tiki hut and of course the saltwater pool. ...

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Summerland Key Vacation Rentals


$filter_name = private-pool