Pet Friendly Vacation Rentals in Summerland Key

(15 rentals)
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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 | 2 BA | Sleeps 6 | Quick View

$155

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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4 BR | 2 BA | Sleeps 8 | Quick View

$357

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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2 BR | 2 BA | Sleeps 4 | Quick View

$153

avg/night

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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 | 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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3 BR | 2 BA | Sleeps 6 | Quick View

$248

avg/night

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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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4 BR | 2 BA | Sleeps 8 | Quick View

$350

avg/night

View Details

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 | 2 BA | Sleeps 6 | Quick View

$148

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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2 BR | 1 BA | Sleeps 4 | Quick View

$95

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 | 2 BA | Sleeps 6 | Quick View

$303

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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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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2 BR | 2 BA | Sleeps 4 | Quick View

$202

avg/night

View Details

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 | 3 BA | Sleeps 6 | Quick View

$316

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

$297

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 | 2 BA | Sleeps 6 | Quick View

$316

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Start your vacation in the Keys off right at Blackbeard’s Escape! This unique home has it all. Main living area on first floors is a 2-bedroom 1 bathroom home with gourmet kitchen, lovely finishes and details plus comfy king size beds. Cooling is great with mini ac splits and large flat screen tv’s ...

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Property Type

Summerland Key House

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Summerland Key Vacation Rentals