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Summerland Key Waterfront Vacation Rentals(51)

51 Results
$2,100 - $2,450
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(14)
  • 5 BR,
  • 4 BA,
  • Sleeps 12
(10)
$5,200
per month
30 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
30 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
(15)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
31 night minimum stay
(3)
$1,595 - $2,700
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night minimum stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 10
(7)
$16,000
per month
28 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
28 night minimum stay
$2,000 - $2,500
per month
30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
30 night minimum stay
$285 - $375
per night
6 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
6 - 7 night minimum stay
(37)
$350
per night
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(9)
$250
per night
6 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
6 night minimum stay
(3)
  • 4 BR,
  • 2 BA,
  • Sleeps 12
$9,450
per month
28 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
36 more choices from the HomeAway Network
  • 2 BR,
  • 1 BA,
  • Sleeps 4
28 night minimum stay
(5)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(7)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 14 night minimum stay
2 Reviews
$3,750
per month
28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
(3)
$2,800
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
(10)
$2,100
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(6)
$1,600
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
(13)
  • 3 BR,
  • 2 BA,
  • Sleeps 7
(4)
$2,500
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 10
7 night minimum stay
(7)
$17,143 - $21,429
per month
28 night minimum stay
  • 5 BR,
  • 4 BA,
  • Sleeps 12
28 night minimum stay
1 Review
$7,200
per month
30 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
30 night minimum stay
$6,500
per month
28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
1 Review
$16,575 - $19,575
per month
28 night minimum stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
28 night minimum stay
$2,800 - $3,200
per month
28 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
28 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 10
28 night minimum stay
2 Reviews
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Recent Summerland Key Reviews

Just as Advertized

5 of 5
Stay was great! Took our own boats and docked two bay boats and fished six people all week offshore and inshore. Protected water for docking, freindly neighborhood for securty, easy access to open water on ocean and bay sides. House was everything advertized it would be and more. We would go back in the drop of a hat.
  • Submitted: Jan 20, 2015
  • Stayed: Jan 2015

We don't get there until Thursday!

5 of 5
We haven't got there yet, but Mike has been the best person to deal with in all our Keys rentals. Thanks Mike.
  • Submitted: Jul 30, 2013
  • Stayed: Jul 2013

Great place for a big family!

4 of 5
Summerland Estate is a great place for a Keys vacation. You are close enough to Key West to hit the town and the night life but far enough away to get the quiet laid back Keys atmosphere. We had 10 in our party and had plenty of room for all of us. My three boys loved the "bachelor" pad downstairs. It was their own little slice of independence. The property is very well maintained and the manager and owner were very accommodating. We spent a lot of time on our boat and caught fish all week. Even caught some nice snapper right off the dock. My kids loved snorkeling off the dock and had some nurse sharks visit us almost every night. We have a 25 ft pontoon boat and the dock and deep water were perfect for even our bulky boat. The kids loved the pool and we enjoyed grilling out quite a bit in the evenings. Great relaxing vacation. Didn't get to use hot tub b/c of leak in it. But since it was summer in the Keys it wasn't an issue. I am sure the leak will be addressed as the rest of the house was well maintained. We will return again! ..
  • Submitted: Jul 23, 2013
  • Stayed: Jun 2013