Summerland Key Vacation Rentals

(24 rentals)
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1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 6 miles to Baja Honda

$150

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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"

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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$950

avg/night

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Key Amenities

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

$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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3 BR | 3 BA | Sleeps 6 | Quick View

$230

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 | 3 BA | Sleeps 6 | Quick View

$223

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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4 BR | 2 BA | Sleeps 8 | Quick View

$366

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 | 2 BA | Sleeps 6 | Quick View

$128

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Enjoy the ultimate peace and quiet offered on Big Torch Key. Located just 5 miles off the Overseas Highway. This pristine area is a true treasure of the lower Keys. This home is nicely remodeled and boasts large spacious room and comfortable furnishing.The shady screened porch overlooks the crystal ...

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Property Type

Summerland Key House

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2 BR | 1 BA | Sleeps 5 | Quick View

$133

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

Sun Kissed you’ll be during your stay at this wonderful home on Ramrod Key!This newly remodeled, tastefully decorated home offers both comfort and style for sun worshippers and fishermen alike. The two bedrooms and two baths have all new comfortable beds, bedding and linens. The living room ...

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Property Type

Summerland Key House

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3 BR | 2 BA | Sleeps 6 | Quick View

$153

avg/night

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Key Amenities

  • Air conditioning
  • 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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3 BR | 2 BA | Sleeps 6 | Quick View

$297

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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4 BR | 2 BA | Sleeps 8 | Quick View

$267

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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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3 BR | 2 BA | Sleeps 6 | Quick View

$160

avg/night

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Key Amenities

  • Air conditioning
  • 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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4 BR | 2 BA | Sleeps 16 | Quick View

$333

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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2 BR | 2 BA | Sleeps 4 | Quick View

$197

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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3 BR | 2 BA | Sleeps 6 | Quick View

$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

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2 BR | 2 BA | Sleeps 4 | Quick View

$120

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Welcome to Buccaneer Boathouse! Pack your floral shirts, swimming gear and sandals and come on down to Little Torch Key in the beautiful Florida Keys. This lovely home is spacious with 2 bedrooms and 2 bathrooms. It offers a large open kitchen, dining and living area for everyone to hang-out and plan ...

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Property Type

Summerland Key House

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2 BR | 2 BA | Sleeps 4 | Quick View

$160

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

On vacation but right at home in this newly remodeled two-bedroom, two-bathroom canal front home! Your boat will also feel at home on the 30’ dock. Relax on the open porch overlooking the canal or in your spacious, bright and airy living room.Cook your catch of the day on the charcoal grill ...

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Property Type

Summerland Key House

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3 BR | 2 BA | Sleeps 6 | Quick View

$142

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

This tropical paradise is just waiting for you and your guests. Located near the end of a quiet lane this custom home has it all. Glorious open bay views from the screened porch for hours of quiet time. The interior has been expertly decorated in Caribbean style with lots of special touches. Large eat-in ...

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Property Type

Summerland Key House

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3 BR | 3 BA | Sleeps 8 | Quick View

$421

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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2 BR | 1 BA | Sleeps 4 | Quick View

$93

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

Kick back and relax in this Island vacation home. Or, enjoy the spacious deck located off the kitchen area, and take in the warm tropical breezes, canal and spectacular sunset skies. Fish from the dock or take advantage of the convenient boating access and cruise out to Looe Key, site of some of the best ...

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Property Type

Summerland Key House

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3 BR | 3 BA | Sleeps 8 | Quick View

2

$197

avg/night

View Details

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

"Incredible Patio & Pool space"

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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$233

avg/night

View Details

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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3 BR | 3 BA | Sleeps 6 | Quick View

$183

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront

About this property

Come enjoy the breathtaking open water views from the multi-level porches of Waterside Bay!This 3 story custom home has 3 bedroom and 3 baths and has upscale yet comfortable living. Complete with a Gourmet Kitchen of stainless steel appliances and granite counters making entertaining a breeze. The ...

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Property Type

Summerland Key House

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3 BR | 2 BA | Sleeps 6 | Quick View

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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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°