Summerland Key Vacation Rentals

(11 rentals)
Blue Marlin

3 BR | 2 BA | Sleeps 6 | Quick View

$160

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Pet Friendly

About this property

Set sail for a glorious Florida Keys vacation at the Blue Marlin. Spacious and comfortable for 6 people in this 3 bedroom, 2 bathroom, Little Torch Key home. Located down a private lane and overlooking the crystal blue waters of Pine Channel, Gulfside.All the rooms are spacious and decorated in peaceful ...

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Property Type

Summerland Key House

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Amazing Elevated Home on a Quiet Canal, Little Torch Key

1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 6 miles to Baja Honda

$145

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Rentals by Owner

About this property

Conchcanary is located on Little Torch Key, in the heart of the Florida Keys. Come relax in our hammocks with a tropical beverage or bring your boat for some fantastic fishing.Enjoy your morning coffee with a canal views from the screened balcony. Newly updated kitchen with top of the line appliances, ...

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Property Type

Summerland Key House

"Honeymoon in the Keys"
Reviewed November 28, 2019

My wife and I spent the first 7 days of our married life living it up in the Keys. We loved it. Kayaking in the bay. Trips to the beach (very different from other beaches). Snorkeling in the ocean! Live ...

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Mermaid's Tale

4 BR | 3 BA | Sleeps 8 | Quick View

$217

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This is the perfect home for an unforgettable vacation in the Florida Keys. This theme inspired home tells a tale of mermaid’s and ocean lore.The custom tile work in all 3 baths is hand made and designed to transport you to ocean vistas. The main level boasts 3 bedrooms, sleeping den, 2 baths and ...

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Property Type

Summerland Key House

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Hogfish Hideout - New Swimming Pool and Cargo Lift

$223

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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 new carpet in the bedrooms. ...

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Property Type

Summerland Key House

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ANOTHER DAY IN PARADISE

3 BR | 2 BA | Sleeps 6 | Quick View

$235

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

It’s more than just another Day in Paradise, it’s an incredibly wonderful and memorable vacation stay in the fabulous Florida Keys!Please come stay with us in this large 3 bed 3 bath heated and chilled pool home on deep water canal in Summerland Key. Entering the home by way of the 2 story ...

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Property Type

Summerland Key House

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Isle Be Back

4 BR | 2 BA | Sleeps 8 | Quick View

$254

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • 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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MARGARITA VILLA

3 BR | 2 BA | Sleeps 6 | Quick View

$141

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Welcome to Margarita Villa! Located in Jolly Roger Estates on Little Torch Key, where you’ll find some of the best deep water boating in the Lower Keys!Decorated in fine island-style this private home is definitely a 5-star proprety. Tile floors, open and airy kitchen, living and dining area ...

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Property Type

Summerland Key Villa

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GONE FISHING

3 BR | 2 BA | Sleeps 6 | Quick View

$182

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

”Gone Fishing” is exactly where you will be during your vacation time at this pristine home on Summerland Key, just 23 miles to Key west and 25 miles to Marathon.Relax and enjoy cocktails and snacks by the heated and chilled swimming pool after a great day exploring all the treasures the ...

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Property Type

Summerland Key House

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Caribbean Dream #8386

4 BR | 3 BA | Sleeps 8 | Quick View

$380

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Florida Keys meets Coastal Chic. This brand new and completely re-imagined Caribbean Dream vacation home in popular Summerland Key (Mile Marker 24) is truly amazing! Totally renovated with meticulous attention to detail in March of 2020. The 3300 s.f.home easily accommodates up to 10 friends or family. ...

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Property Type

Summerland Key House

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Salty Retreat

3 BR | 3 BA | Sleeps 8 | Quick View

$326

avg/night

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Key Amenities

  • Air Conditioning
  • Full 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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Keys Life

3 BR | 3 BA | Sleeps 8 | Quick View

$169

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

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Summerland Key Vacation Rentals

Summerland Key Weather

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7524°  6518°
JANUARY
Ocean 7222°
7624°  6619°
FEBRUARY
Ocean 7222°
7926°  6921°
MARCH
Ocean 7423°
8127°  7222°
APRIL
Ocean 7826°
8529°  7624°
MAY
Ocean 8127°
8831°  7926°
JUNE
Ocean 8328°
8932°  7926°
JULY
Ocean 8529°
8932°  7926°
AUGUST
Ocean 8731°
8831°  7826°
SEPTEMBER
Ocean 8529°
8529°  7624°
OCTOBER
Ocean 8328°
8127°  7222°
NOVEMBER
Ocean 7926°
7725°  6719°
DECEMBER
Ocean 7524°