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Summerland Key Vacation Rentals with air conditioning(140)

140 Results
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(41)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night min stay
(11)
$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
(15)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night min stay
(14)
  • 5 BR,
  • 4 BA,
  • Sleeps 12
7 night min stay
(10)
$1,250
per night
6 night min stay
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 10
6 night min stay
1 Review
$175 - $225
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
$5,200
per month
30 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
30 night min stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
(34)
$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)
$165 - $193
per night
4 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night min stay
(34)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(24)
$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
(16)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
31 night min stay
(3)
$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)
$16,000
per month
28 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
28 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
(7)
  • 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
(7)
  • 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
$120
per night
3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
3 night min stay
(15)
$180 - $200
per night
4 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
4 - 7 night min stay
(11)
$800 - $1,250
per week
7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
7 night min stay
(4)
$3,000 - $3,300
per month
28 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 night min stay
(8)
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Recent Summerland Key Reviews

Awesome little gem in paradise!

5 of 5
Georgia thank you for an absolutely perfect place to stay. We had a great time scuba diving. I highly recommend Ron who lives there in Venture Out and works as an instructor and guide at Looe Key Resort Dive Shop just around the corner. I will definitely be returning for some more R&R as soon as possible. The place was great and had everything we need for an affordable rate. Thanx again Georgia!
  • 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

Great time!

5 of 5
This place is fantastic! We vacationed here for a week with our family consisting of our 17 year old and 7 year old. We had the most fun sitting on the back dock and fishing. We were able to catch some really interesting fish! We loved grilling and watching all of the boats during the evening. The mornings were spent watching the dolphins swim by. The house was so comfortable and the amenities were fantastic. Everything we needed for the kitchen was right there. The best part was sitting at the table, eating, and enjoying the view. We loved that the guest bedroom had two beds so that each child had their own. Plus a tv for their enjoyment. My daughter and I enjoyed riding the bikes to the store (within the community) The pool was great and never crowded and the security staff were some of the nicest people we met! We highly recommend this property, and would stay again, unfortunately our dates were not available. Robin has any information you may need and she was a pleasure working and communicating with.
  • Submitted: Feb 8, 2015
  • Stayed: Jun 2014