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Summerland Key Vacation Rentals & House Rentals - 3 Rentals Available

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3 Vacation rentals

1 / 12

Summerland Key House

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning

from $143 / night

(3)

1 / 20

Summerland Key House

  • 4
  • 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This house was great. Had everything you could ask for. The owner even called to make sure we made it ok and if we needed anything. Best view, plenty of space absolutely gorgeous couldn't of asked for better...”
- Review left on 08/19/2014

$233

Excellent (3 reviews)

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from $233 / night

(4)

1 / 3

Summerland Key Guest house

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We rented the Conch House for our honeymoon and it was perfect! We loved the secluded feeling and the private beach. Carol was wonderful to work with and had fresh eggs and champagne waiting for us in our fridge. She picked fresh veggies for us to...”
- Review left on 04/20/2016

$393

Excellent (4 reviews)

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from $393 / night

Your search has been expanded 37 miles to include more rentals

(2)

1 / 23

Cudjoe Key House - 3.3 miles away

  • 2
  • 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The view was outstanding, the property had great amenities, and the home had all items as advertised. We were happy campers...”
- Review left on 03/13/2017

$157

Very Good (2 reviews)

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from $157 / night

(8)

1 / 20

Ramrod Key House - 3.5 miles away

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Very clean has all the essentials. Loved being able to have the boat right there. Definately will be back”
- Review left on 09/17/2015

$133

Excellent (8 reviews)

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from $133 / night

(5)

1 / 13

Ramrod Key House - 4.2 miles away

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We enjoyed our vacation in this spacious home. We had 5 adults and 2 small boys and never felt cramped. The wood floors and opened concept allowed us to spend a lot of time together. Great dock for the boat! Just a couple of minutes to open water....”
- Review left on 08/02/2016

$117

Very Good (5 reviews)

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from $117 / night

(48)

1 / 34

Cudjoe Key House - 5.7 miles away

  • 6
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$415

Very Good (48 reviews)

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from $415 / night

(2)

1 / 12

Big Pine Key House - 8.1 miles away

  • 2
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“We really enjoyed coffee on the deck overlooking the canal, bird watching, fishing and spending evenings at Sunset Park watching the sunset. The home was immaculate, spacious and the bedding was so comfortable. The owners were excellent to work...”
- Review left on 03/20/2017

$133

Excellent (2 reviews)

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from $133 / night

1 / 25

Big Pine Key House - 9 miles away

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $131 / night

(8)

1 / 10

Big Pine Key House - 10.4 miles away

  • 3
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The house is located in a secluded neighborhood located on Coupon Bight. Key deer amble around with ease near and on the grounds. Key West is located 33 miles west and Marathon is 17 miles east. Big Pine has a Winn Dixie so you can get all your food...”
- Review left on 05/10/2015

$313

Excellent (8 reviews)

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from $313 / night

1 / 8

Sugarloaf Key House - 11.4 miles away

  • 5
  • 10
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $500 / night

(4)

1 / 22

Key West Townhouse - 31.3 miles away

  • 2
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning
“The property we rented was wonderful. It was very clean and spacious for my family to enjoy while we were attending a wedding. The grounds area was well maintained. Sitting by the pool was relaxing and to see iguanas come right down from the trees...”
- Review left on 05/29/2016

$201

Very Good (4 reviews)

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from $201 / night

(27)

1 / 23

Key West House - 31.3 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$196

Very Good (27 reviews)

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from $196 / night

(11)

1 / 24

Key West House - 31.3 miles away

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$245

Very Good (11 reviews)

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from $245 / night

(4)

1 / 24

Key West House - 31.4 miles away

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$245

Excellent (4 reviews)

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from $245 / night

1 / 24

Key West Townhouse - 31.4 miles away

  • 3
  • 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

from $252 / night

(15)

1 / 23

Key West House - 31.4 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$196

Very Good (15 reviews)

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from $196 / night

(2)

1 / 29

Key West Townhouse - 31.4 miles away

  • 3
  • 6
  • 3 nights min
  • Ask about children
  • Air conditioning
“The place was very nize,cozy, clean and comfortable, felt very much at home would definitely come back again and rent the same place”
- Review left on 08/09/2016

$400

Excellent (2 reviews)

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from $400 / night

1 / 17

Key West House - 31.7 miles away

  • 3
  • 6
  • 30 nights min
  • Ask about children
  • Air conditioning

from $100 / night

(7)

1 / 12

Key West Condo - 33.2 miles away

  • 2
  • 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$296

Very Good (7 reviews)

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from $296 / night

(118)

1 / 28

Key West Apartment - 33.2 miles away

  • 2
  • 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
“we can"t say enough about the condo or Pam. She takes good care of her rental. Always clean and comfortable.The balcony overlooks the pool area which is well maintained. Pam is always available to answer any questions you might have. We stay the...”
- Review left on 12/03/2016

$200

Excellent (118 reviews)

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from $200 / night

(50)

1 / 36

Key West Condo - 33.2 miles away

  • 2
  • 6
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoyed our stay at the Sunrise Suite. The place was bright with sunshine. It was clean, comfortable, nice sitting balcony and close to Duval Street. It had everything you would need for your stay. You could walk thru the complex and cross the...”
- Review left on 03/06/2017

$209

Excellent (50 reviews)

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from $209 / night

(3)

1 / 6

Key West Apartment - 33.2 miles away

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$296

Very Good (3 reviews)

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from $296 / night

(1)

1 / 23

Key West House - 33.4 miles away

  • 3
  • 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This house is immaculately kept and one of the few houses on a canal in KW. Beautiful interior and plenty of room in the bedrooms. The pool overlooks the canal and has an absolutely beautiful view! If you want a house that makes you feel like you're...”
- Review left on 03/10/2015

$133

Excellent (1 reviews)

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from $133 / night

(19)

1 / 20

Marathon House - 34 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The house was just as pictured. Swimming in the gulf and canoeing was great. Waking up to that beautiful view every morning was wonderful. It's centrally located and close to everything. Definitely would stay again...”
- Review left on 01/03/2017

$200

Excellent (19 reviews)

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from $200 / night

1 / 24

Marathon Condo - 34.8 miles away

  • 3
  • 6
  • Min stay varies
  • Ask about children
  • Air conditioning

from $144 / night

(4)

1 / 9

Marathon House - 35.3 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“The canal front cottage was beautiful . Super clean perfectly furnished, hey 3 flat screens First class cooking utensils. Grill chairs by the dock, water, fish station & great light for night activity. Owner and manager readily available, most...”
- Review left on 08/30/2015

$156

Excellent (4 reviews)

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from $156 / night

(13)

1 / 25

Key West Apartment - 35.7 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$236

Very Good (13 reviews)

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from $236 / night

(2)

1 / 18

Key West Condo - 35.8 miles away

  • 3
  • 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$284

Excellent (2 reviews)

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from $284 / night

(29)

1 / 23

Key West Apartment - 35.9 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$231

Very Good (29 reviews)

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from $231 / night

(6)

1 / 24

Key West Apartment - 35.9 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$376

Very Good (6 reviews)

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from $376 / night

(29)

1 / 24

Key West Apartment - 35.9 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

$231

Very Good (29 reviews)

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from $231 / night

(2)

1 / 15

Key West Condo - 35.9 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“My boyfriend and I stayed here for approximately five nights. The condo is situated on the 4th floor with an amazing view of the ocean right out on the balcony. The condo was very clean and well-maintained. All of the appliances worked appropriately...”
- Review left on 01/04/2017

$200

Excellent (2 reviews)

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from $200 / night

(9)

1 / 20

Key West Condo - 35.9 miles away

  • 2
  • 6
  • 1 night min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Excellent location walking distance to Smather's beach. Gorgeous view of the ocean and perfect location. Full 2 bedrooms and 2 baths as well as a full kitchen and living room. Very clean and modern. Rain Forest pathway to the pool and grilling...”
- Review left on 08/12/2016

$251

Very Good (9 reviews)

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from $251 / night

1 / 24

Key West Apartment - 35.9 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from $231 / night

1 / 16

Marathon House - 36.3 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1000

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from $1000 / night

1 / 17

Marathon Condo - 36.6 miles away

  • 1
  • 4
  • 30 nights min
  • Child friendly

$134

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from $134 / night

(3)

1 / 15

Key West House - 36.9 miles away

  • 3
  • 6
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“I have stayed at the Brass Palm Villa several times and I would never stay anywhere else on the island. It is decorated beautifully and exceptionally well maintained. There are many places to relax inside and outside the home. I especially enjoy the...”
- Review left on 10/10/2010

$200

Excellent (3 reviews)

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from $200 / night

(28)

1 / 24

Key West Apartment - 37 miles away

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$165

Very Good (28 reviews)

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from $165 / night

(6)

1 / 16

Marathon House - 37 miles away

  • 5
  • 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The best family vacation home. House Was perfect in every way. My kids had a blast in the pool and jacuzzi. Very clean. We will definitely rent Margarita on the Gulf again...”
- Review left on 03/16/2017

$500

Excellent (6 reviews)

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from $500 / night