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Summerland Key Waterfront Vacation Rentals(125)

125 Results
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night min stay
(12)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(42)
$995 - $1,700
per week
6 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 7 night min stay
(13)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
(17)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night min stay
(14)
  • 5 BR,
  • 4 BA,
  • Sleeps 12
7 night min stay
(10)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(35)
$1,250
per night
6 night min stay
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 10
6 night min stay
1 Review
$5,200
per month
30 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
30 night min stay
(5)
$175 - $225
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
$120 - $184
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night min stay
(27)
$150 - $193
per night
4 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night min stay
(34)
$17,143 - $21,429
per month
28 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 12
28 night min stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
31 night min stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
(16)
$150 - $200
per night
3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night min stay
(11)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night min stay
(5)
$1,595 - $2,700
per week
7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night min stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
(7)
$16,000
per month
28 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
28 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
28 night min stay
(5)
$120 - $150
per night
2 - 3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night min stay
(8)
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
3 night min stay
(7)
$2,450 - $2,950
per month
30 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
30 night min stay
$180 - $200
per night
4 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
4 - 7 night min stay
(12)
$800 - $1,250
per week
7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night min stay
(5)
$3,000 - $3,300
per month
28 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night min stay
(8)
$995 - $1,550
per week
7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
1 Review
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
6 - 7 night min stay
(37)
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Recent Summerland Key Reviews

Awesome honeymoon choice

5 of 5
My husband and I had a wonderful time at Blue Heaven. He called it Eden. He was happy to see it was just like the pictures. We were able to fish daily off the back patio/dock. Minutes from Key West. Spent one day golfing at the Key West Golf Club with lunch at Boondocks afterwards. Awesome blackened grouper sandwich. Then one day shopping and site seeing in Key West. We recommend Conch Republic Seafood Company restaurant. A day at Bahia Honda beach and a couple days at the pool. The rental was clean and roomy. Very reasonable price for an entire week stay. Gated with security guard. Shopping nearby so you don't have to eat out unless you just want to. Quiet and peaceful. Very relaxing. Owner was very nice, responsive and helpful. I would recommend this home for a couple or a small family of 3 or 4. We have already booked for next year. Bringing the family and renting 2 homes. Can't wait! :)
  • Submitted: May 17, 2015
  • Stayed: May 2015

A little gem on the ocean

5 of 5
What a fantastic location! Close to everything with all the comforts of home. We definitely look forward to coming back year after year!
  • Submitted: Apr 28, 2015
  • Stayed: Apr 2015

Family Fun

5 of 5
The Bug Shack was fantastic. I took my family for boating, fishing, snorkeling, and relaxation. The house has everything we needed to enjoy our time. We enjoyed cooking our catch fresh off the boat. The pool was great for the kids. What a beautiful place to be. We will definitely be back to the Bug Shack. Maybe we will be lucky enough to catch some lobsters next time!
  • Submitted: Mar 10, 2015
  • Stayed: Aug 2014