Summerland Key House Rentals

(24 rentals)
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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

$150

avg/night

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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"
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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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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Sunset Paradise

3 BR | 3 BA | Sleeps 8 | Quick View

$350

avg/night

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Key Amenities

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

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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BOW CHANNEL MANOR

3 BR | 3 BA | Sleeps 6 | Quick View

$219

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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SUNKISSED

2 BR | 1 BA | Sleeps 5 | Quick View

$129

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed

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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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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THE POINTE

2 BR | 2 BA | Sleeps 4 | Quick View

$194

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Pets allowed

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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Summerland Key House

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PALM HARBOR

3 BR | 2 BA | Sleeps 6 | Quick View

$157

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Palm Harbor located at mile marker 23 in Cudjoe Gardens is the perfect spot to unwind and relax in the Florida Keys sunshine. Just minutes from Cudjoe Gardens marina for gas, bait and your fishing needs. Deep draft boating will accommodate up to 4 foot draft.Large and spacious inside with open kitchen ...

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Property Type

Summerland Key House

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BIG TORCH RETREAT

3 BR | 2 BA | Sleeps 6 | Quick View

$126

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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BUCCANEER BOATHOUSE

2 BR | 2 BA | Sleeps 4 | Quick View

$117

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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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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KEY ISLAND GETAWAY

4 BR | 2 BA | Sleeps 16 | Quick View

$333

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed

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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BARBADOS LANDING

2 BR | 2 BA | Sleeps 4 | Quick View

$156

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed

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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CRUIKSHANK

3 BR | 3 BA | Sleeps 6 | Quick View

$226

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Pets allowed

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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CASA AZZURRA

4 BR | 2 BA | Sleeps 8 | Quick View

$353

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed

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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Salty Retreat

3 BR | 3 BA | Sleeps 8 | Quick View

$395

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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Blue Marlin

3 BR | 2 BA | Sleeps 6 | Quick View

$158

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Pets allowed

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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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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SAILFISH MANOR

3 BR | 2 BA | Sleeps 6 | Quick View

$292

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed

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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WATERSIDE BAY

3 BR | 3 BA | Sleeps 6 | Quick View

$179

avg/night

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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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PIRATE'S COVE

2 BR | 1 BA | Sleeps 4 | Quick View

$91

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed

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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OWL'S NEST

3 BR | 2 BA | Sleeps 6 | Quick View

$139

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed

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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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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CASA TURQUESA

3 BR | 2 BA | Sleeps 6 | Quick View

Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Pets allowed

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


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