Summerland Key Vacation Rentals with Boat Dock

(26 rentals)
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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

Minimum 28-day rental. NO, this is NOT available to rent for fewer than 28 nights. Please don't ask.Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property....two large cottages (each two-bedroom) and a main house overlooking the ...

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Property Type

Summerland Key House

"Perfect Tropical Oasis"

This is an incredible find! If you’re interested in this property, do not hesitate! In almost 30 years of traveling at least 15 times to Florida, this is by far the nicest place we’ve stayed. Whether ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Rentals by owner

About this property

The Key-ver beach house is an oceanfront vacation rental in the world-famous Florida Keys on the southern end of Summerland Key, mile marker 25. The house is an open floor plan with panoramic Atlantic Ocean views and a large wrap-around deck. Two bedrooms (the oceanside bedroom has a king bed and the ...

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Property Type

Summerland Key House

"Excellent Location - Excellent Hosts"

Fantastic location, the view from the sunroom is fantastic. Postcard sunrises to start the day! House was very well equipted with everything we needed during our stay, hosts reached out to check on us ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Welcome to Palm Mansion! This large family home with 5 bedrooms and 3 full baths is located on a wide, deep canal suited for large boats and there is tons of dock space for all your water toys! There is plenty of parking as well, enough for trailers and RV's. The pool is private and very large....kids ...

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Property Type

Summerland Key House

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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"

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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4 BR | 2 BA | Sleeps 8 | Quick View

1

$264

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront

About this property

Make your memories at the Aloe House on Cudjoe Key! This home is located on a beautiful crystal clear canal with plenty of dockage for up to a 25 foot boat. The canals here provide great access to some of the best fishing in the Florida Key – Bahia Azul, “Bay of Blue” is exactly the ...

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Property Type

Summerland Key House

"Great Home to rent on Little Torch Key"

Great home on a canal with easy access to the ocean. The extensive dock is wonderful. Very comfortable home with with a good flow.

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$283

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 4 | Quick View

$179

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

Serenity found in the Florida Keys! This home is situated on a beautiful canal in the Jolly Roger Estates of Little Torch Key. There is plenty of room for your boat with access to the best boating, fishing, diving, and snorkeling in the lower Keys.The exterior of this home boasts a large concrete ...

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Property Type

Summerland Key House

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2 BR | 2 BA | Sleeps 4 | Quick View

$137

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 | 1 BA | Sleeps 4 | Quick View

$110

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

1

$342

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • 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

"Wonderful House"

Our family throughly enjoyed our stay at this house. It was very clean and there was plenty of room. It was perfect for the fishing families. Plenty of dock space, a bait freezer, and an ice machine. We ...

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2 BR | 1 BA | Sleeps 5 | Quick View

$150

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

$277

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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3 BR | 2 BA | Sleeps 6 | Quick View

$358

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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3 BR | 2 BA | Sleeps 6 | Quick View

$157

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 | 2 BA | Sleeps 4 | Quick View

$169

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

$225

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 | 1 BA | Sleeps 6 | Quick View

$200

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

No steps here! Looking for the perfect ground level home for your FL Keys vacation? Look no further, Casa Morada is the place for you!Florida Keys Vacation Rentals – Amazing canal front 3 bed conch style house located in prestigious community of Summerland Key Cove. It is the first canal from ...

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Property Type

Summerland Key House

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3 BR | 3 BA | Sleeps 8 | Quick View

$450

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 ...

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Property Type

Summerland Key House

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3 BR | 2 BA | Sleeps 6 | Quick View

2

$267

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

"Outstanding location for fishing, boating, & diving!"

Stayed at this gem before and after Lobster mini season. The pool was perfectly refreshing after a day in the sun on the water. There are several free boat ramps nearby. Great proximity to the Looe key ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Summerland Cottage-Relax At Our Little Piece of Paradise!Host Missy Proctor Phone meeting is required before booking approval. Please email me for my number and any questions you may have :)Come and Enjoy our Cozy Little , Nostalgic Keys Stilt Cottage on Summerland Key! Enjoy Open water views ...

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Property Type

Summerland Key Cottage

"Our new home away from home"

We are a family of three with a 16-year-old son. We rented on the adjacent Cudjoe Key for the last 15 years. We focus on fishing, snorkeling, and exploring the area by boat. This year, our usual rental ...

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3 BR | 2 BA | Sleeps 6 | Quick View

1

$179

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

"Nice home, greatl canal good to work !"

Not my first time with action keys, always had good result with everyone at this company! Wish they would rework there utilities policy , it’s hard enough to pay rent for a month.

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2 BR | 2 BA | Sleeps 4 | Quick View

$224

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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4 BR | 2 BA | Sleeps 8 | Quick View

$417

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

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 6 | Quick View

$250

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

$317

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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4 BR | 2 BA | Sleeps 8 | Quick View

$417

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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Summerland Key Vacation Rentals