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Summerland Key Vacation Rentals with Air Conditioning(60)

60 Results
$2,100 - $2,450
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
(13)
  • 5 BR,
  • 4 BA,
  • Sleeps 12
(10)
  • 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)
$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
(36)
$250
per night
6 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
6 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
$19,000
per month
28 - 30 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
28 - 30 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
  • 4 BR,
  • 3 BA,
  • Sleeps 8
  • 4 BR,
  • 3 BA,
  • Sleeps 8
  • 2 BR,
  • 2 BA,
  • Sleeps 6
  • 3 BR,
  • 2 BA,
  • Sleeps 6
  • 3 BR,
  • 3 BA,
  • Sleeps 8
  • 2 BR,
  • 2 BA,
  • Sleeps 7
41 more choices from the HomeAway Network
$2,800
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
(10)
$3,750
per month
28 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night minimum stay
(3)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
28 night minimum stay
(4)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 14 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 4
30 night minimum stay
(12)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
(7)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
(21)
$817 - $1,600
per week
7 - 31 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
7 - 31 night minimum stay
(5)
$1,600
per week
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night minimum stay
(13)
$7,200
per month
30 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
30 night minimum stay
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Recent Summerland Key Reviews

Million Dollar View!

5 of 5
The house is comfortable and well equipped. It is in a great location--close to Key West and great snorkeling. But the best part, by far, of the house is the view of the ocean. We sat on the screened in porch and enjoyed the view every day at breakfast and again in the evening. It is a great vacation house to relax in.
  • Submitted: Oct 21, 2014
  • Stayed: Oct 2014

Perfect Keys Vacation!

5 of 5
We brought 5 families together for a family reunion. This place was spectacular! The house is well-stocked and accommodated everybody needs. With that many people think somebody would've had a gripe, but that was not the case ! Everyone absolutely loved this property and this was everyone's favorite vacation. It was nice to be able to do your own thing and stay off the beaten path! We fished, snorkled, and rented a boat that was safe in the canal. His place has it all and I would definitely recommend staying here!
  • Submitted: Jul 19, 2014
  • Stayed: Jun 2014

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