Houses Key West

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283 houses

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“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. 1 hour 19 minutes

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$229

Casa Havana

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

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$1,003

Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access

Key West house

3 bedrooms / 2 bathrooms / sleeps 8

“Nice alternatif for hotel” We were on the boat with only 2 people, so plenty of place ! We liked the marina and the boat very well. Something completely different than an hotelroom ... We had perfect weather so we used the different terraces on the boat depending on the wind and sun. The only point what could be better is the quality of the bedding (sheets, blankets, towels...) For this price you expect some better quality. Anyway, when we wil go back to the us I certainly will search for something similar to stay on

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$258

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

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$479

The Water's Edge

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

“Perfect for a Memorable Key West Experience!” My family and I absolutely loved staying in this beautiful Key West home. Located in Truman Annex (a quiet, private community in Old Town Key West), the location is perfect for whatever you wish to do during your Key West experience. Ocean Paradise has gorgeous views from the 3rd level balcony, a wonderful screened-in porch on the main level (perfect for al fresco dining), and an incredible pool area with a larger than expected private pool and stunning landscaping that provides both shade and privacy. The home's interior is both spacious and functional, including lovely furnishings and everything you need for a memorable vacation in beautiful Key West. Just as important to us was the ease in managing our visit to Ocean Paradise. The owner and his staff were absolutely incredible to work with throughout the entire rental process. We had originally scheduled our visit for the 2014 Thanksgiving holiday week. However, a need arose which required us to cancel that planned stay. The property owner was gracious enough to work with us in our desire to reschedule our visit for May 2015, demonstrating a focus on and respect for his guests throughout the entire process. Our Key West vacation, and specifically our week-long stay in Ocean Paradise, was undoubtedly a memorable experience for me, my husband and our two adult children (as well as the little "furry" member of our family who also joined us for our Key West adventure). We will be returning to Key West, and when we do, Ocean Paradise will be our chosen "home away from home" during our stay!

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$842

Admiral's Lane

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

“Fabulous family rental” We have stayed in Key West for four years now. This was the best rental property so far. The location is perfect for beach days and walking both ends of Duval at night. The property itself had all the amenities we needed and was run well by the property managers. The major reason we didn’t give five stars is that all of the tv’s were from the 90’s. They offered cable but on screens that are archaic. Not great for unwinding or catching up with March Madness. For this level of home/rental, the owners could spring for even just ONE flat screen.

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$625

President's Walk

Key West house

2 bedrooms / 1 bathroom / sleeps 4

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$195

Sunny View

Key West house

1 bedroom / 2 bathrooms / sleeps 2

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$110

The Mermaid's Garden

Key West house

4 bedrooms / 5 bathrooms / sleeps 8

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$625

Artist Garden

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Beautiful House, sometimes loud” We stayed at the artist's Garden for one week. There were 4 adults and an 11 month old. The house is gorgeous, lots of interesting art. Some of it we had to move out of reach of our 11 month old, but that was easy enough. The only downside to this house is that it's located across the street from the post office. It wouldn't be bad except the bedroom windows face the post office. Some mornings the postal trucks banged around starting at 4:52 am! I finally had to put on a white noise app every night to drown them and the roosters out. (The roosters is a Key West issue, not this houses's ;-) ) .. It was in a great location, easy to access all the restaurants, Duval Street and Mallory square. The pool is very close and well maintained. We definitely would consider staying here again, but if a different house in Truman annex were available not close to the post office, we'd probably choose that first. We would definitely go through at Home in Key West, though! They were wonderful and helpful. They also recommended using The Hip Tourist for renting baby equipment and it was perfect!!!

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$285

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 22

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 2 hours 33 minutes

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$1,797

Big house

Key West house

5 bedrooms / 5 bathrooms / sleeps 12

“Bachelorette in Key West” I rented this house for my sister-in-law's bachelorette weekend in Key West. The house was spacious, clean, and overall the best place I've ever stayed! It was worth every penny!

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$750

Island Style

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

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$769

Sunshine Key West

Key West house

2 bedrooms / 3 bathrooms / sleeps 5

“Perfect Home for Key West” This place has all the amenities you need! It was our first time renting a home and it couldn't have been more perfect! Quiet neighborhood, but not too far from the action of Duval.

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$107

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 15 minutes

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$1,260

Key West Found

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Great rental” This is a great location. Walked to everything including snorkeling every day at Zachery beach. Stayed for a week without a car or bikes. Townhouse is extremely clean, maintained and well furnished. Need to add a few more dishes (i.e. bowls). Décor was nice but a few minor changes would make it great. Love the shaded porch. All in all a great rental. Truman annex very secure and quiet.

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$265

Lighthouse Villa

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

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$193

Duval Breeze

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Warm and inviting condo” The condo is very cozy and inviting. I would definitely go back. Everything you need is right there (even a starter kit) in the condo. Duval street is heaven and parking is safe. We walked to everywhere (restaurant, groceries, shopping). What a great place to stay..

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$240

First Breath

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

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$107

Key West Gulf front Home with private dock and pool.

Key West house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 46 minutes

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$326

"Little Paradise" Historic Seaport Old Town Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 16 minutes

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$490

Boat House

Key West house

1 bedroom / 2 bathrooms / sleeps 2

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$93

Beautiful Home Located In Quiet neighborhood

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

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$339

Verandah

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“We had a delightful stay, enjoyed meeting warm and welcoming peo” This was our second year at verandah and once again it was just perfect. Can't wait to return in 2014. Key west is definitely our happy place.

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$100

Coconut Cottage

Key West house

1 bedroom / 2 bathrooms / sleeps 2

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$77

Duval On The Square

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“A really good place to stay” Duval Square is a very good location. Crowd noise is not a problem. However the parrots from the New York restaurant below can get annoying. The inside of the apartment is nicely done. The balcony's overlooking the square are nice but are in need of painting. Service from the rental company was excellent. They respond quickly to requests. Bringing the baggage up to the apartment is easier when you use a shopping cart and the elevator. If a cart is not in the garage take the elevator up to the 2nd floor. They are usually left by the elevator. The worst problem is the parking at the check in site. It is extremely tight and it is a damaged fender waiting to happen. The service once inside is very good.

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$100

Ibis

Key West house

1 bedroom / 1 bathroom / sleeps 2

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$75

Linger Longer

Key West house

2 bedrooms / 1 bathroom / sleeps 5

“Clean and well provisioned” Townhouse was centrally located, clean, and all basic household goods (paper towels, laundry detergent etc.) were there to meet our needs for the week. I would definitely recommend this unit.

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$195

tropical Casita

Key West house

1 bedroom / 2 bathrooms / sleeps 2

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$107

Poinciana House

Key West house

1 bedroom / 2 bathrooms / sleeps 4

“Awesome” The house was just as Historic Hideaways pictured and described...beautiful. The house was very clean, a pool service came twice a week to clean the pool and Tim, (agent) was very informative and helpful. Everything was supplied from towels to suntan lotion. There was nothing we needed to bring except our clothes & food. I would definitely stay here again.

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$385

Crowner's Jewel

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“First visit to Key West” Took our family to Key West for the first time and we had a wonderful time. Rental was in great location and good condition. My family will visit again.

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$220

Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Fabulous luxury home in Fabulous Key West” Beautiful, private, historic 2 BR/2 bath home, lovely heated pool, outdoor dining & living areas in addition to most attractive indoor spaces. Wonderful Old Town neighborhood. Can walk, cycle, & Lyft everywhere (including great restaurants)--no car needed. 2nd BR is in the guest house beyond the pool--fabulous outdoor shower completes the "only-in-Key West" ambiance. The owner, Kim, is super responsive.

Responds fast! avg. 2 hours 49 minutes

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$557

Royal Palm

Key West house

2 bedrooms / 3 bathrooms / sleeps 5

“Key west is always fun” 3 of us rented a condo in the foundry located in the Truman annex. I have stayed here before and knew what to expect. Any unit in Truman annex is an easy walk to everything there is to do downtown. Since it is a gated community a person feels very safe there. These units have fully equipped kitchens plus a washer & dryer. My first stay in the foundry was several years ago and these units are starting to show their age. The steps up to the porch had become unattached from the porch which made it a slight inconvenience. Also we flipped some light switches and nothing came on. Don't know if bulbs were burned out or if the switches didn't work. I reported all of this to the rental agency and hopefully these things have been taken care of. Would I go back to the foundry? You bet I would. Probably next year.

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$270

The Prive

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“What a wonderful place to forget the long cold winter and renew” The house was beautiful . The neighborhood was quiet and peaceful. It was everything we had hoped it would be. Everything you could possibly need in a house was there. The house was spotless, bright and airy. The back yard was beautiful! If you need a place to relax and rejuvenate this is it! I can't wait to rent it again!

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$325

Key Lime Pie

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Loved Off Season Key West” Spent a month in this very secluded house within walking distance of everything, including the marina, Duval Street and my favorite Watering Hole, Finnegan's Irish Wake pub. Renting in October, the off season, meant I got to experience an uncrowded Key West. And best of all, at the end of the month, to experience Fantasy Fest in its entirety. What a rush. House was wonderful. Had it all including a hot tub. Private parking, a real plus in Key West. Plan to do it again.

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$87

Duval Square

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“First Key West visit” It was our first visit to the Keys and our stay with Historic Hideaways was the cherry on top. They were a pleasure to work with and the home was so nicely decorated, perfectly clean and organized. Everything we needed was right there. The location couldn't have been better. We were within walking distance of everything. I cannot wait to stay and visit again.

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$280

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

1 bedroom / 1 bathroom / sleeps 4

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$572

A Place In Paradise

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Excellent Location” Our condo was extremely well prepared for our week long vacation, great decorations and included everything one needs for a week....washer/dryer, ironing board, etc. The location of this condo could not be better ....a couple of blocks away from all of the down town restaurants and close to the beautiful waters that only the "Keys" have to offer and fantastic sunsets. Highly recommend.

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$245

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