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Price: high to low
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Ocean Hideaway Key West Retreat Private Nature preserve and Ocean views await
Stock Island condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 58 minutes
Price per night from
$544
* Caribbean Conch Key West Condo offers delightful extras *
Stock Island condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 58 minutes
Price per night from
$498
*Spring Discounts Stay on the Ocean Last minute Specials Book & Save *
Stock Island condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 58 minutes
Price per night from
$624
Tropical Oasis in Key West with magical Key West Charm throughout
Stock Island condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 58 minutes
Price per night from
$859
New Listing!!! - 61 SUNSET KEY - Exclusive Island Getaway On Sunset Key, Shared
Stock Island house
2 bedrooms / 3 bathrooms / sleeps 4
Responds fast! avg. 3 hours 32 minutes
Price per night from
$180
ISLAND ESCAPE! - Amazing Condo, Steps From Duval Street & Short Walk To Southern
Stock Island condo
1 bedroom / 1 bathroom / sleeps 4
Responds fast! avg. 3 hours 32 minutes
Price per night from
$164
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
$896
New Listing!!! 70 SUNSET KEY - Incredible Sunset Key Island Home, Community Pool
Stock Island house
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 3 hours 32 minutes
Price per night from
$180
THE CONCH CHATEAU - Beautifully Updated Conch House Located In The Heart Of Key
Stock Island house
4 bedrooms / 2 bathrooms / sleeps 9
Responds fast! avg. 3 hours 32 minutes
Price per night from
$180
New Listing!!! KEY LIMETINI - Small Space & Big Fun, Close to Beaches, Shopping
Stock Island studio
Studio / 1 bathroom / sleeps 2
Responds fast! avg. 3 hours 32 minutes
Price per night from
$121
Price per night from
$201
Responds fast! avg. 3 hours 32 minutes
Price per night from
$180
New Listing! BLUE BAYOU - Perfect Key West Location W/ Pool, Close To Beach, Duv
Stock Island condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 3 hours 32 minutes
Price per night from
$180
New Listing! MARGARITAS AND MEMORIES - Beautiful, New Town Home W/ Amazing Backy
Stock Island house
3 bedrooms / 3 bathrooms / sleeps 6
Responds fast! avg. 3 hours 32 minutes
Price per night from
$180
SALIDA DEL SOL - Rare Key West Waterfront, Close To Beaches, Duval Street & Worl
Stock Island house
3 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 3 hours 32 minutes
Price per night from
$177
Great rentals within 20 miles that match your search
Charming 3bedroom/2bath home in the Florida Keys
Cudjoe Key house
3 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$130
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
$320
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
Responds fast! avg. 2 hours 31 minutes
Price per night from
$430
Downtown Key West Oasis, Tropical Paradise Steps from Duval & Ft Zach
Key West apartment
2 bedrooms / 1 bathroom / sleeps 4
Responds fast! avg. 2 hours 58 minutes
Price per night from
$344
** Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret **
Key West house
1 bedroom / 1 bathroom / sleeps 4
“The perfect place to stay in Key West” This property is just 1 block off Duval -- but closer to the quiet, quaint side. I was so impressed with the accomodations -- fully equipped! We could have stayed there a month! The grounds are beautiful, lush, tropical and quiet. Staff was super friendly -- it is also very private with a large locking wrought iron gate keeping the units apart from the street -- we loved everything about it! We will stay here again on our next visit for sure!~
Responds fast! avg. 2 hours 58 minutes
Price per night from
$446
“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
$379
Anchor Drop in Key West modern elegance, luxury finishes. Bike to Old Town
Key West apartment
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 58 minutes
Price per night from
$682
Luxurious Renovation with sweeping ocean views. A true Paradise
Key West apartment
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 58 minutes
Price per night from
$716
“Outstanding!” 1800 altantic was the perfect place to stay for our "friends" reunion. Our condo was clean and well equipped. The place was extremely safe and secure.
Responds fast! avg. 2 hours 58 minutes
Price per night from
$1,145
Seaside Place Key West FL 5 Bedroom House 4 Baths
Key West house
5 bedrooms / 4 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
Responds fast! avg. 3 hours 42 minutes
Price per night from
$2,119
“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
$2,060
Price per night from
$1,144
Price per night from
$1,488
Price per night from
$1,144
** Best Value in Key West Just 1 block from Duval Open April & May 2022**
Key West apartment
2 bedrooms / 1 bathroom / sleeps 4
Responds fast! avg. 2 hours 58 minutes
Price per night from
$192
“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. 3 hours 1 minutes
Price per night from
$343
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
$2,004
Top floor, two bedroom,two bath condo with private balcony,close to the Ocean
Key West condo
2 bedrooms / 2 bathrooms / sleeps 6
Responds fast! avg. 2 hours 26 minutes
Price per night from
$487
Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes
Key West townhouse
2 bedrooms / 1 bathroom / sleeps 6
Price per night from
$516