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Key West Waterfront Vacation Rentals(168)

168 Results
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night min stay
(47)
$350 - $484
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(96)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 night min stay
(60)
  • 3 BR,
  • 2 BA,
  • Sleeps 7
5 night min stay
(37)
$5,000 - $7,500
per month
28 - 30 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
28 - 30 night min stay
(24)
  • 5 BR,
  • 4 BA,
  • Sleeps 14
4 - 6 night min stay
(67)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
6 night min stay
(50)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(42)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
6 night min stay
(21)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
6 night min stay
(31)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
27 night min stay
(14)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
6 night min stay
(28)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night min stay
(39)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
28 night min stay
(9)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
4 - 6 night min stay
(38)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
4 - 6 night min stay
(44)
$295 - $560
per night
3 - 5 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night min stay
(36)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night min stay
(17)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 6 night min stay
(10)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
27 night min stay
(6)
$750 - $950
per night
3 - 5 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 10
3 - 5 night min stay
(16)
$2,800 - $3,500
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(9)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
27 night min stay
(7)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night min stay
(5)
$750 - $790
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night min stay
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 6 night min stay
(4)
$289 - $299
per night
3 - 4 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 - 4 night min stay
(3)
$220 - $460
per night
3 - 5 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night min stay
(5)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night min stay
(19)
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Recent Key West Reviews

Awesome 60th birthday get-away!

5 of 5
Private cottage close to everything! Cottage has everything you could need plus! Fort Zachary Taylor next door, short walk to Duval, Coast Guard ship to your right out the back door for tour, and fishing off the boardwalk to the right of the ship. My husband enjoyed swimming in the complex's pool every afternoon to cool off after our activities. Seaplaned to Dry Tortugas and snorkeled, 2 fishing charters, and explored Key West. Was thankful for the cool, comfortable cottage to chillax in! Awesome vacation and home-away from home!
  • Submitted: May 17, 2015
  • Stayed: May 2015

Property was gorgeous and well maintained.

5 of 5
Shel was great as a resource as well as friendly business professional to work with. The house was perfect for what we were looking for, and provided plenty of room. I would recommend the owners replace the oven which was far below expectations. I would not hesitate to call Shel for me next trip as he was professional, friendly, flexible, accommodating, and provided us with a point person which to contact for any reason. Thanks again Shel!
  • Submitted: May 13, 2015
  • Stayed: Mar 2015

This place has it all!

5 of 5
Top o' The Town has become our home away from home. Our 3 month stay was as wonderful this year as in past years. The condo offers everything needed for a luxurious and relaxing stay. The condo is very large, by any standards, and offers ample social and private space, both inside and outside. The kitchen is equipped with top of the line appliances. The furnishings are comfortable and storage is plentiful. The rooftop terrace is a great place to grill, relax and take a dip in the small pool. The view of the sunset is phenomenal from the rooftop - a peaceful place to watch the day come to a close. I can't forget the elevator. It is such a convenience after shopping and offers privacy and security. I can't say enough about Shel, our guest services manager. It is such a pleasure to have him meet us and welcome us to our island getaway. He offers recommendations about things to do, new restaurants and old favorites. He is quick to respond if any issue arises and follows up immediately to make sure all is ok. He will also just "check in" to make sure everything is going well. He is genuinely interested in making sure our vacation is perfect. Already looking forward to next year.
  • Submitted: May 13, 2015
  • Stayed: Jan 2015