Summerland Key Vacation Rentals with Private Pool

(9 rentals)
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Summerland Key House | On the beach
7 BR | 5.5 BA | Sleeps 14 | Quick View
Sleeps 14, 7 bedrooms, 5.5 bathrooms
5 reviews

$750

avg/night

$750
avg per night
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Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

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

Featured review

"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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Summerland Key House | On the beach
4 BR | 5 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 5 bathrooms

$360

avg/night

$360
avg per night
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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atlantic. Sea Wall has room for (1) 24' boat. This home can sleep 7 adults and 2 small children. There are 4 bedrooms and 4-1/2 bath. Fully stocked modern kitchen, great out door space ...

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Property Type

Summerland Key House

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Summerland Key House | On the beach
6 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 4 bathrooms

$658

avg/night

$658
avg per night
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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Beautiful Ocean Front Home with six bedroom/Four bath. New memory foam mattresses in King and Queen rooms. Enjoy the heated pool, dock and beach. Located on Cudjoe Bay with panoramic view of the Atlantic and deep water swimming. Kayaks are provided for your enjoyment. There is a huge screened in porch ...

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Property Type

Summerland Key House

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Summerland Key House
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms

$292

avg/night

$292
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

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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Summerland Key House
2 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 2 bedrooms, 2 bathrooms

$266

avg/night

$266
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

This is truly an incredible, well-designed, and appointed Summerland Key home! You will love the interior design of this palace, with cathedral ceilings, a sunken living room and a lofted office/additional sleep space. A very large dining room leads into the enormous, updated kitchen, fit for any chef. ...

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Property Type

Summerland Key House

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Summerland Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$313

avg/night

$313
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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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Summerland Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$282

avg/night

$282
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

Featured review

"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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Summerland Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

$357

avg/night

$357
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

Featured review

"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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Summerland Key House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
3 reviews

$232

avg/night

$232
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

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

Featured review

"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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Summerland Key Vacation Rentals