Vacation Rentals & House Rentals in Key West

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123 house rentals

Steps to Duval, Old Town Charm -Grand Bahama Suite

Key West apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Can't wait to return” We loved staying at the Grand Bahama suite. It was spacious, clean and centrally located just a street from all the action. We loved the courtyard and pool. I was a little concerned about parking but it worked out fine for us. We just coordinated with the other tenants. We will definitely be staying here again.

Responds fast! avg. 3 hours 22 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$377

Spectacular Atlantic Ocean View Condo (MONTHLY)

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranquil. The patio faces south so you don't get blasted with the morning or evening sun making it very comfortable having your morning coffee or evening cocktail while enjoying the view. The owners have put a lot of thought into furnishing and accessorizing the unit. Tess and Mimi were wonderful to work with (Mimi met us at the condo and had great advice on where to eat, what to do...)I have stayed in several condos and this was by far my favorite, if your thinking of staying here you will not be disappointed. I will definitely be back the next time I visit the keys.

Match: Shared outdoor pool (heated)

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Price per night from

$330

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

2 bedrooms / 3 bathrooms / sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$572

Best Location, 1/2 Block to Duval, Bimini Suite

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Perfect!” This was the perfect size suite for 4 adults, with a little pool oasis right off our doorstep, in the center of it all without the noise of Duval. Loved every second of my stay!

Responds fast! avg. 3 hours 22 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$297

Center of It All - Paradise Island Suite

Key West apartment

2 bedrooms / 1 bathroom / sleeps 6

“Great location in the heart of Old Town Key West, just a block off Duval..” We stayed in the Paradise Suite. Great front porch to hang out on, pool in back with pergola for lounging. Place was set up perfect, pool towels hanging by the door, bathroom had necessary items, kitchen well set up with needed items as well. Very well maintained and cleaned, bedding all set. Wi-Fi and other amenities available. Perfect for two couples, with room for even an extra guest. Driveway accommodates three cars, unmetered parking around the corner. Local market just 1/2 block away, and the highly recommended Thirsty Mermaid restaurant on the corner. Owner and managers very available and responsive. Will certainly stay again.

Responds fast! avg. 3 hours 22 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$285

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

Match: Shared outdoor pool (heated)

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Price per night from

$229

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. 1 hour 45 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$229

1/2 Block to Duval, World of its own -Nassau Suite

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Our wedding family stayed here awesome” Fabulous. Clean roomy pool fantastic. Short walk to schooners Wharf Both inside and outside area were excellent

Responds fast! avg. 3 hours 22 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$320

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect place to experience Key West” This is a lovely condo with a tropical, quiet view. Many extras are included: beach towels, bikes, and kitchen supplies. The pool area was our favorite spot, and we had coffee every morning on the balcony with chairs for all 6 of us. My husband enjoyed watching March Madness on the large T.V. Kathy did a fantastic job with all communications and provided great tourist tips. We would definitely stay here again!

Responds fast! avg. 2 hours 36 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$430

Key West Florida Beachfront Condo

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

“Better than the photos” Condo is perfectly located at the beach. Well designed for easy living both inside and out. Great advise on where to visit and eat thanks

Match: Shared outdoor pool (heated)

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Price per night from

$401

Welcome Aboard! Relax, unwind, enjoy the water! in key west

Key West yacht

4 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$285

A Touch Of Havana In Key West

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 2 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$352

Campbell Suite

Key West apartment

1 bedroom / 2 bathrooms / sleeps 2

“Comfortably furnished and decorated with a very convenient locat” We really enjoyed staying at the Campbell Suite. It served our requirements nicely. The amenities and location were excellent. Potential visitors do need to note that the entrance to the unit is on the 2nd floor, and there is also a circular metal staircase to get from the living area of the unit up to the bedroom. So occupants do need to be reasonably fit to do the stairs and get their luggage up there. We had no problems with this, but others need to be aware depending on their individual circumstances. As far as improvements, we did notice that there was some water that leaked into the closet on the 2nd floor and accumulated a bit in the center of the closet floor after the heavy rain the morning of Tue. 3/25. Didn't cause any problems for us but just wanted to bring it to someone's attention to check into before it gets worse.

Match: Shared outdoor pool (heated)

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Price per night from

$200

Coconut Beach

Key West apartment

1 bedroom / 2 bathrooms / sleeps 4

Match: Shared outdoor pool (heated)

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Price per night from

$262

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!

Responds fast! avg. 1 hour 47 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$319

Isle Of View II

Key West boathouse

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 23 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$228

Havana Hideaway

Key West apartment

2 bedrooms / 3 bathrooms / sleeps 5

“Wonderful Experience!” I had a great experience with Historic Hideways during my 5 week stay in Havana Hideway. Everything exceeded my expectations. A great place and exteremely friendly service with Historic Hideways. I would recommend to anyone.

Match: Shared outdoor pool (heated)

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Price per night from

$310

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Key West townhouse

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 52 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$359

Key West Living-Oceanside Catamaran "Spirit of the Wind"

Key West yacht

3 bedrooms / 1 bathroom / sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$353

The Banyan Resort at Key West

Key West apartment

2 bedrooms / 1 bathroom / sleeps 6

“Wonderful week at The Banyan Resort!!” My husband and I recently stayed in a 2 bedroom/1Bath unit at The Banyan Resort and we were extremely pleased with everything!! Everyone we encountered from the front desk, housekeeping, grounds personnel and other guests were warm and welcoming! The unit was very spacious and comfortable and you can"t beat the location. It's within walking distance of all attractions and Fort Zachary Taylor State Park. The owner was very responsive to all of my questions and a pleasure to work with and we look forward to being repeat guests at The Banyan Resort.

Match: Shared outdoor pool (heated)

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Price per night from

$263

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.

Match: Shared outdoor pool (heated)

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Price per night from

$270

Banana Key

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Key West in December.” We chose Banana Key just a few days before we actually got there due to a last minute vacation opportunity. I worked with Tim at Historic Hideways and couldn't have been happier with him and the staff in this office. He assured me that we would love it there and he was right. The home was beautiful, the bed was extremely comfortable and the kitchen well stocked with everything we needed for our time there. We were on a working vacation and found the living room to have plenty of electrical outlets which helped us in being able to accomplish our work efficiently and comfortably in order for us to get out and enjoy the sunshine. We had a couple of maintenance issues such as a hot water heater problem and a smoke detector activation, but when I called H.H they took care of those issues promptly. Last but not least, location location location!! You could not ask for better access to all of the great shops, bars and restaurants just a few blocks off of Duval. We had bicycle delivered to us and we rode bikes nearly every day. We would totally recommend this rental and were very pleased with the staff at Historic Hideways.

Match: Shared outdoor pool (heated)

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Price per night from

$310

Walk or Bike!! Truman Annex: 3 BIKES, 2 PORCHES, A POOL, WIFI, & PARKING

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 47 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$196

Shipyard

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

“Wish I could live here all year.” Check-in was very quick and Tim did an excellent job at explaining the area and providing us with useful information regarding restaurants and activities. I really felt that he did an above-and-beyond job at making sure we had a great vacation. The house was clean and anything that we needed (cleaning supplies, detergent, etc) as well as information regarding the house was available to us. The location was nice. Most everything was within walking distance or was a $5 cab ride. The only thing we found a bit annoying was that the community pool hours were not followed by the community staff. Often we found the pool locked during the middle of the day. Of course I understand that Historic Hideaways has no control over this as they simply own one of the lots on the site. After a long day of swimming, charters, and walking around town, we were always looking forward to relaxing at the house. My fiance and I really enjoyed our stay. We're already planning to return next year!

Match: Shared outdoor pool (heated)

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Price per night from

$185

Rose Treehouse

Key West studio

Studio / 1 bathroom / sleeps 2

Match: Shared outdoor pool (heated)

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Price per night from

$175

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.

Match: Shared outdoor pool (heated)

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Price per night from

$280

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 38 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$342

Tee by the Sea - NO DAMAGE FROM HURRICANE IRMA , Plus 7 Bikes FREE

Key West apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

Responds fast! avg. 2 hours 50 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$286

Luxury 3BD/3B Penthouse Condo at Galleon Resort, Old Key West

Key West condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 0 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$915

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

Match: Shared outdoor pool (heated)

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Price per night from

$265

HISTORIC KEY WEST - Cigar House - Sleeps 4

Key West house

1 bedroom / 1 bathroom / sleeps 4

Match: Shared outdoor pool (heated)

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Price per night from

$572

Key West Hyatt Windward Pointe

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Shared outdoor pool (heated)

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Price per night from

$229

Truman Annex Shipyard with Tropical Garden

Key West apartment

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 27 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$351

Sunrise at Seaside Condo 2 Bedroom

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“A cozy second home with an amazing view” The location is great! We were near shopping centers and easy access to anywhere we'd desired to go. Rooms were spacious, clean and neat. The view from the balcony was amazing. Everything was perfect! My parents loved the condo and was so happy that I've chosen to stay at Sunrise. I would definitely recommend this place and would visit again.

Responds fast! avg. 2 hours 1 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$184

The Courtyard

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

“Great place!” Was very pleased with our rental. Perfect for two people. Nicely maintained and a great location. We were very happy and would definitely stay again.

Match: Shared outdoor pool (heated)

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Price per night from

$225

Sunrise At Seaside Condo 2 bedroom 2 bath

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Exactly what we needed.” Owner responded in timely manner and was pleasant and answered all questions. The unit was easy to find and close to the airport. We worried about airport traffic noise interfering with sleep, but never heard them inside the condo. Condo was clean and had washer and dryer inside the unit. It was amazing to be able to do laundry when I wanted. Pool was clean, heated, and refreshing. Loved having private covered parking. It kept the car nice and cool when you got in. We'll definitely visit again in the future!

Responds fast! avg. 2 hours 1 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$171

HISTORIC KEY WEST - Conch House - Sleeps 5

Key West house

2 bedrooms / 1 bathroom / sleeps 5

Match: Shared outdoor pool (heated)

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Price per night from

$571

A Touch of Bermuda in Key West

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Lovely Home and Great Location for our Key West Vacation” We had a great time at The Touch of Bermuda Cottage on Truman annex. We knew this was a good location from previous trips, and we also knew we wanted to find an individual home with all the amenities we needed for our stay in Key West. The Cottage certainly fitted the bill. It was very spacious, well equipped, with lots of homely touches, and had a nice private back yard where we could breakfast in the morning or come back after a long day to relax in the evening. On two floors so plenty of privacy for our party, and 2 bathrooms which isn't the case with every 2 bed property in the annex. The owner, Jack, was very responsive and helpful before we arrived and real pleasure to deal with. The Cottage is close to the Truman entrance, so easy to walk to all the main attractions, but far enough away to be nice and quiet after dark. The communal pool is a very short walk away down the back path. Overall it's a good rental property in a well kept development. We would go back there.

Responds fast! avg. 2 hours 2 minutes

Match: Shared outdoor pool (heated)

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Price per night from

$401

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