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Responds fast! avg. 3 hours 56 minutes
Price per night from
$516
Ocean Hideaway a Key West Nature retreat close to Smathers & 15 to Duval
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$859
Caribbean Conch 5 Minutes to Smathers Beach & 10 minute Bike Downtown - Value
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$859
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$134
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$859
Leaward Isle close to the Ocean' & a short bike downtown. Best value at 1800
Stock Island condo
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Price per night from
$859
Island Escape: Charming Condo Just Steps From Duval Street, Near Southernmost Po
Stock Island condo
- 1 bedroom
- 1 bathroom
- sleeps 4
Responds fast! avg. 2 hours 34 minutes
Price per night from
$124
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
Price per night from
$180
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$623
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$526
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$445
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$484
Price per night from
$347
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
Price per night from
$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
Price per night from
$179
Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK
Stock Island house
- 4 bedrooms
- 3 bathrooms
- sleeps 11
Price per night from
$801
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
Price per night from
$180
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$472
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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
Price per night from
$263
Price per night from
$668
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
Price per night from
$179
Responds fast! avg. 3 hours 56 minutes
Price per night from
$206
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
$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
$328
“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
$1,302
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
Price per night from
$287
Price per night from
$792
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
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