Updating...
Price per night from
$385
$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Pool, Hot Tub, D
Sugarloaf Key house
- 4 bedrooms
- 4 bathrooms
- sleeps 12
Responds fast! avg. 2 hours 34 minutes
Price per night from
$179
Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home, Private Pool and Dockag
Sugarloaf Key house
- 4 bedrooms
- 4 bathrooms
- sleeps 8
Responds fast! avg. 2 hours 34 minutes
Price per night from
$179
Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water V
Sugarloaf Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 2 hours 34 minutes
Price per night from
$179
Price per night from
$1,142
Beautiful quiet neighborhood. Sunsets! Huge Pool!
Sugarloaf Key house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
Responds fast! avg. 30 minutes
Price per night from
$321
Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage & D
Sugarloaf Key house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 2 hours 34 minutes
Price per night from
$179
Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor Di
Sugarloaf Key house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
Responds fast! avg. 2 hours 34 minutes
Price per night from
$179
Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Private
Sugarloaf Key house
- 3 bedrooms
- 3 bathrooms
- sleeps 8
Responds fast! avg. 2 hours 34 minutes
Price per night from
$179
Great rentals within 20 miles that match your search
Fisherman's Paradise in the Heart of Big Pine Key
Big Pine Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$114
30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock.
Summerland Key house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$161
“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!
Price per night from
$574
“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.
Price per night from
$329
“Location, Location, Location” We were a group of 8 and rented the entire compound! The place was in an amazing location that was easily accessible to everything. We had everything we needed onsite and if we had any questions, Phyllis was always just a phone call away. The music and talking at night from the cigar lounge was a bit loud, but nothing we couldn't tolerate. The only suggestion I'd make is to buy an ionizer for the first two units to help with the cigar smell....again, nothing intolerable, but could make a world of difference. Can't wait to come back for another visit! THANK YOU!
Price per night from
$1,303
2 Bedroom, 2 Bath Condo with private balcony and Close to the Ocean
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
“We'll be back...” We found this condo to be very clean and comfortable. We enjoyed sitting at the pool as well. Paul, the caretaker, was very pleasant and most accommodating. We shared the condo with another couple for our two night stay. It was wonderful to have our privacy (2 BR/2 baths) but still be able to share the kitchen/living room area with our friends. We had a rental car so found the location easy for shopping, dining, sightseeing on other keys and, of course, Duval Street.
Price per night from
$488
“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.
Responds fast! avg. 2 hours 7 minutes
Price per night from
$344
Price per night from
$108
“Wonderful” Close to everything! Furnishings just the best. We stayed upstairs in the 2 bedroom 1 large bath. Great wrap around porch up stairs and down. Our key Westies were welcomed which was a plus for us! Overall Stephanie has done a great job and her sister was really helpful. Planning on returning!!!!
Price per night from
$134
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 6
“Perfect location and great value!” From the moment we arrived, this condo was everything we wanted without breaking the bank. We spent days looking for a place in Key West for Christmas week. What was available was crazy expensive, so to be honest when we found this place for the price we were slightly apprehensive. It is close to everything, the check-in and check-out were easy, the people who live in the complex were very friendly and welcoming and always willing to offer advice on where to go and what to do. Everything worked and was clean and we could not have asked for a better vacation. Can't wait to go back!
Price per night from
$435
Henry's Piece Of Paradise On The Ocean In Key West
Key West apartment
- 2 bedrooms
- 2 bathrooms
- sleeps 5
“nice place” Accommodations were nice Good view Henry was great to work with
Price per night from
$465
“Key West, Spring 2012” In a word,our stay with you was ”wonderful”. We have been to Key West on several occasions and have loved every visit. Staying in Truman annexe was even more special. We all felt like we were at home with everything we needed. You must feel blessed to live in that part of the world. We will be looking for a job for our 19 year old son,Tom. He wants to come and work over in Key West. We have just arrived home and everything seems grey, and much colder than Key West. Depending on finances( the pound-dollar rate is not too good just now) we hope to come back soon. We will definitely be giving you a call.I would recommend your accommodation and company to future holiday makers. Love and blessings John,Jayne,Jack and Tom
Price per night from
$380
BIG POOL! Across Street from Beach! SEASIDE PLACE, Key West - 5/5 w/parking
Key West house
- 5 bedrooms
- 6 bathrooms
- sleeps 12
“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today
Price per night from
$2,124
Price per night from
$1,491
“February visit to Key West” Our family stayed at the Main House for 4 nights and loved it. The location was fabulous! Loved the houses and gardens!!! The owner was very nice and considerate of us. If we get back that is where we would want to be!!
Price per night from
$2,065
Price per night from
$1,147
“Great condo” Great condo - nicely decorated and most well stocked kitchen ever. Everything was so neat and clean and there was an abundance of supples. Would highly recommend
Responds fast! avg. 1 hour 58 minutes
Price per night from
$321
Top floor, two bedroom,two bath condo with private balcony,close to the Ocean
Key West condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$488
Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes
Key West townhouse
- 2 bedrooms
- 1 bathroom
- sleeps 6
Price per night from
$919
Price per night from
$141