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Responds fast! avg. 3 hours 38 minutes
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$514
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
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$859
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
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$859
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
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$134
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
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$859
Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
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$859
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$3,993
The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Poo
Stock Island house
- 4 bedrooms
- 2 bathrooms
- sleeps 9
Responds fast! avg. 2 hours 34 minutes
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$180
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$622
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$510
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$525
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$523
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$525
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$484
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$346
J Ferrara #9: Charming Studio Oasis, Steps from Duval Street, Southernmost Point
Stock Island studio
- Studio
- 1 bathroom
- sleeps 2
Responds fast! avg. 2 hours 34 minutes
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$179
Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oas
Stock Island house
- 5 bedrooms
- 4 bathrooms
- sleeps 10
Responds fast! avg. 2 hours 34 minutes
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$179
Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK
Stock Island house
- 4 bedrooms
- 3 bathrooms
- sleeps 11
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$797
70 Sunset Key: Experience Idyllic Island Life, Shared Pool, Beach Access & Latit
Stock Island house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 2 hours 34 minutes
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$180
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$471
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$654
All-Inclusive Yacht Margarita Flaca: Marina OR Anchor on the Ocean: Free Charter
Stock Island yacht
- 1 bedroom
- 1 bathroom
- sleeps 6
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$262
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$523
Summer Love: Sunny Serenity Awaits, 2nd Floor Key West Condo, Shared Pool, Steps
Stock Island condo
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 2 hours 34 minutes
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$179
Responds fast! avg. 3 hours 38 minutes
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$205
Great rentals within 20 miles that match your search
“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.
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$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!
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$1,296
LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH
Key West apartment
- 1 bedroom
- 1 bathroom
- sleeps 4
“Fantastic Stay!” My husband and two sons (21 & 24) stayed in this condo over Christmas. This was our first stay in Key West and we wanted to be close to everything, but yet not right on Duval St. This location was perfect; literally a stones throw away from Duval St. The unit inside was decorated very lovely and had all the amenities one would need. I found the owners were nice to do business with, especially Deb who I mostly communicated with. My family and I enjoyed our stay in Key West immensely, we had so much fun! We met many very friendly people out and about town. We would love to visit again, if we do, we would like to stay in this condo or the Bella Vita, the owner's other condo.
Responds fast! avg. 14 minutes
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$286
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$788
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$619
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.
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$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
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$342
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$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!!!!
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$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
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$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
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$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
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$1,482