Summerland Key Vacation Rentals

(7 rentals)
Keys Escape

3 BR | 3 BA | Sleeps 6 | Quick View

$771

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront

About this property

Escape from all your cares at this wonderful vacation rental on Cudjoe Key. Just the spot to unwind and let your hair down. There are 3 bedrooms and 3 baths plus a recreation room for the kids to get away. Open and airy living and kitchen area for friends to gather.Full walk around screened porches ...

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Property Type

Summerland Key House

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South Point Shores

3 BR | 2 BA | Sleeps 6 | Quick View

$686

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Private Pool

About this property

This bright, very spacious and inviting, nicely-maintained Sugarloaf Key home is located just 20 minutes north of Key West. Nestled back in a beautifully manicured neighborhood and not far from Sugarloaf Lodge and Marina, you will have nearby access to boating, fishing, kayaking and a few local restaurants.An ...

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Property Type

Summerland Key House

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Green Turtle Landing

3 BR | 2 BA | Sleeps 6 | Quick View

$600

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

Sugarloaf Key is one of the most desirable islands in the Lower Keys. Large roomy lots, plenty of biking and walking trails in the area. Kayaking , boating and diving are just some of the water sports you will enjoy during your stay.Green Turtle Landing is just the right spot to spend your Florida ...

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Property Type

Summerland Key House

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Waterside Bay

3 BR | 3 BA | Sleeps 6 | Quick View

$714

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Private Pool

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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Caribbean Dream

4 BR | 3 BA | Sleeps 8 | Quick View

$857

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This spacious, Caribbean-style vacation home comes equipped with its own private swimming pool and great deep-water canal. This beautiful home has three stories including a super play room off the pool area with a ping-pong table and a big screen TV for the kids.The 2nd floor accommodates a large ...

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Property Type

Summerland Key House

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Bahia Azul

4 BR | 2 BA | Sleeps 8 | Quick View

$986

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Private Pool

About this property

Bahia Azul, "Bay of Blue" is exactly the perfect spot for your next Florida Keys adventure. The open water views are just stunning and spectacular. Its location at the end of the street makes this a very private get-away.This large home will accommodate all your friends and family with 4 ...

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Property Type

Summerland Key House

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Casa Turquesa

3 BR | 2 BA | Sleeps 6 | Quick View

$886

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Pet Friendly
  • Private Pool

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°