Luxury Vacation Rentals in Summerland Key

(15 rentals)

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • 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"

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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3 BR | 3 BA | Sleeps 8 | Quick View

$394

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Come live the Salt Life at Salty Retreat! Stay at this luxury top of the Line tropical style home on Summerland Key. Located in a very popular subdivision on Lagoon Drive with deep boating access.This home is 'five stars' the moment you pull into the paver circular driveway. Sitting on two lots with ...

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Property Type

Summerland Key House

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4 BR | 2 BA | Sleeps 8 | Quick View

$358

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

This extraordinary island castle will make you feel like the royal family! With four bedrooms and five bathrooms you will not have to share your space! Start your day boating, fishing or kayaking and then return for a cool dip in the pool! Relax on the expansive screened in porch with a drinks and appetizers ...

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Property Type

Summerland Key House

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3 BR | 3 BA | Sleeps 8 | Quick View

$350

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Spectacular sunsets and open water views at this 3 BR 3 BA home on Summerland Key. Brand new dock for your large boat with quick access to the open ocean, gulf & back country. This home is like new, built in 2015, it has 1800 square feet and 10 foot ceilingsThe fully furnished kitchen ...

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Property Type

Summerland Key House

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4 BR | 2 BA | Sleeps 8 | Quick View

$350

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

Looking for that perfect Florida Keys Get Away? You found it here!Located on prestigious Summerland Key with some of the best deep-water boating, diving and fishing in the Lower Keys. Super easy access to superior fishing spots.This upscale home is complete with 4 bedrooms and 2 baths. Beautifully ...

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Property Type

Summerland Key House

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3 BR | 3 BA | Sleeps 6 | Quick View

$317

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Enjoy many peaceful days and evenings at Cruikshank Isle, situated right on the tip of Cruikshank Island on Summerland Key where astounding sunsets and ocean vistas will be yours.The grounds are very shady and groomed, right at the waters edge. Plenty of dockage on the canal side and spacious outdoor ...

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Property Type

Summerland Key House

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3 BR | 2 BA | Sleeps 6 | Quick View

$304

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

It will be love at first sight when you arrive at Sailfish Manor on Summerland Key.You will be greeted by a large southern style veranda complete with 4 rocking chairs. The double French doors lead to the expansive living area and up style chef’s kitchen. Granite counter tops, gas range and ...

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Property Type

Summerland Key House

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$267

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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2 BR | 2 BA | Sleeps 7 | Quick View

$256

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront

About this property

This is truly an incredible, well-designed, and appointed Summerland Key home! You will love the interior design of this palace, with cathedral ceilings, a sunken living room and a lofted office/additional sleep space. A very large dining room leads into the enormous, updated kitchen, fit for any chef. ...

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Property Type

Summerland Key House

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3 BR | 2 BA | Sleeps 6 | Quick View

1

$250

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

"Scam. Do not book"

They were a scam. Not a legit business. Do not send them any money. They second I wanted to provide a verifiable form of payment which would release to them upon property being actually seen and keys provided, ...

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3 BR | 2 BA | Sleeps 6 | Quick View

$249

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Pet friendly

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.This stylish home is outfitted in Florida tropical style with cool and comfortable leather in the living ...

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Property Type

Summerland Key House

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3 BR | 3 BA | Sleeps 6 | Quick View

$225

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront

About this property

Welcome to Bow Channel Manor and step back in time to Old Florida! You’ll find this plantation style home remeniscent of Florida past! Enjoy family-style vacationing on a private 4 acre parcel of land on Upper Sugarloaf Key.The grounds are like a playground. There is a full-size heated pool ...

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Property Type

Summerland Key House

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3 BR | 3 BA | Sleeps 6 | Quick View

$220

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

Luxury waterfront accommodations await for the whole group. This stately home has all the best of everything. The large great room has lots of seating. 42″ Sony flat-screen, hi-def TV with surround sound makes you feel like you are right in the middle of the action. Kitchen is a chef’s delight ...

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Property Type

Summerland Key House

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3 BR | 3 BA | Sleeps 8 | Quick View

3

$202

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • 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

"Keys life"

Enjoyed our stay at Keys Life. The home was beautiful. The weather was quite windy so we weren’t able to get out as much as we wanted in our boat but we were able to get some nice lobster! It was nice ...

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2 BR | 2 BA | Sleeps 4 | Quick View

$202

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

This lovely 2 bedroom, 2 bathroom home, situated at the end of Bay Drive on both open water AND a corner canal, is the best the Lower Keys has to offer.This newly remodeled interior has a well-equipped gourmet kitchen that will be a pleasure to create those memorable family meals. The bedrooms are ...

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Property Type

Summerland Key House

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Summerland Key Vacation Rentals