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Price per night from
$383
$and D0llar$: 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
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
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
Price per night from
$1,140
Beautiful quiet neighborhood. Sunsets! Huge Pool!
Sugarloaf Key house
- 4 bedrooms
- 2 bathrooms
- sleeps 8
Responds fast! avg. 30 minutes
Price per night from
$319
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
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
$160
Price per night from
$172
Fisherman's Paradise in the Heart of Big Pine Key
Big Pine Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$113
“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
$327
“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
$1,296
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
$485
“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
$342
Price per night from
$107
“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
$133
“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
$378
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
$2,111
“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!!
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$2,053
Price per night from
$1,482
Price per night from
$1,140
Price per night from
$1,140
“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
$319
6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location
Key West villa
- 6 bedrooms
- 7 bathrooms
- sleeps 16
Price per night from
$1,997
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
$485
Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes
Key West townhouse
- 2 bedrooms
- 1 bathroom
- sleeps 6
Price per night from
$913
Price per night from
$140
Price per night from
$235