Be sure to check our SPECIALS PAGE for any seasonal specials on nightly rentals. No matter if you are coming to Key West for a long weekend, week-long stay, or month-long getaway, we offer some of the finest nightly and monthly rentals in town. Our vacation homes and condos are conveniently located around Old Town Key West.
While some are close to Duval Street, others are on a quaint quiet lane in the heart of the island. The weather in Key West is warm and sunny nearly year-round. If you have more time, we offer weekly and monthly vacation homes with one, two, three, and four or more bedrooms. Many have gorgeous pools and lush tropical back yards.
While some are close to Duval Street, others are on a quaint quiet lane in the heart of the island. The weather in Key West is warm and sunny nearly year-round. If you have more time, we offer weekly and monthly vacation homes with one, two, three, and four or more bedrooms. Many have gorgeous pools and lush tropical back yards.
Services
We are here to manage every aspect of keeping your Key West vacation rental booked and ready for guests to enjoy. We want you to make the most out of your investment in the Keys without having to do the busy work involved with managing it. What that means for you is we take professional photos, write descriptions, and offer marketing to potential guests to fill your calendar.
Key West Hideaways offers nightly vacation rentals throughout the Key West area. Many of our properties are in close proximity to the downtown area while others offer a short walk to the beach or are right on the open water with a spectacular view. We have rentals to accommodate any budget and any size group.
Looking for a romantic getaway in Key West? Consider one of our vacation rentals for you and your partner. Located throughout the Old Town section and most are just a short walk or bike ride to attractions, beaches, great restaurants and bars. We offer help with booking tours and can make suggestions on things to do while you are here in Key West.
Our 2 bedroom nightly rentals offer room to spread out. Situated mostly in Old Town Key West, our rentals are close to it all. Some may be a short walk to the beach while others are just a short stroll from Duval Street, the main hub of our downtown area. You will find our rentals to be well appointed with all the amenities you need for your stay.
We offer well appointed Key West vacation homes by the night so you can be flexible in your stay on our island. Our larger vacation rentals are made to accommodate larger groups. Perfect for weddings, family reunions or for a group of friends reuniting in Key West! Ask about our other group rentals that are available too!
Reviews (22)
Sasha Bohen
Oct 14, 2021
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Brandon Charlotte
Sep 21, 2021
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Tawna Thompson
May 26, 2021
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We had a wonderful experience with Key West Hideaways! When our plans got cancelled in 2020 they worked with us on the cancelation. They were very helpful in getting us rescheduled when the trip was back on in 2021. The property was great, so comfortable, and a great place to spend a week. Then when our trip was unexpectedly extended, they worked with to help is find another property we could stay at the last minute. The second property was also comfortable and a fun place to stay. Overall they helped turn what could have been a very stressful situation into a fun and easy vacation.
Ed Hudak
Apr 24, 2021
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Positive: Professionalism, Quality, Responsiveness, Value
Bobby and Randy were the best. We stayed in the The Colony -- Island Style unit. It was extremely clean, safe and the area around the pool was cleaned and swept daily. It was walking distance to all main attractions in Key West. Book early. WE are planning our return visit.
Bobby and Randy were the best. We stayed in the The Colony -- Island Style unit. It was extremely clean, safe and the area around the pool was cleaned and swept daily. It was walking distance to all main attractions in Key West. Book early. WE are planning our return visit.
Shaun Gallagher
Dec 24, 2020
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The Windsor place homes are amazing. These houses and their collective landscape are beautiful, and located in the perfect location on the island. The kitchens and decks are both ready for the most discerning chef to feel at home. The spaces inside the home are perfect for entertaining or relaxing. More bathrooms than you could possibly need. Nicely appointed. If you need anything, check a cabinet or closet; chances are they have already thought of it.
What more could anyone ask for?
What more could anyone ask for?
Katelyn Brown
Jul 21, 2020
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I’m writing this review as we are sadly making our way back to the Ft. Lauderdale Airport. This trip was our 4th trip down to Key West and our 2nd time staying with Key West Hideaways. Our first stay was at the eyebrow house with private deck and hot tub. Amazing spot, private, has that key west vibe, and location was perfect. This trip we had booked the same suite but the deck needed repair work so they accommodated us with a new place. They really went out their way to give us that private laid back feel. We had no problem staying in a different suite because it was just another reminder to
Cody M.
Jul 14, 2020
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Location for Orange Blossom is very good, several blocks from Mallory Square and about 500 feet from Duval Street. Check-in was easy, parking is a block away from residence, you can only load and unload in front of residence. Inside was clean. Pull out sofa was very uncomfortable (could feel the springs & bars). Had to leave hot tub covered and running during the day so it would get hot. Fridge gets cool after about 24 hours but not “cold”, freezer is cold enough to keep ice frozen. Blender, toaster, microwave, oven and grill with some pots/pants included. Outlets throughout house need to be
Mark Carter
Jun 23, 2020
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Due to the Covid-19 Pandemic I was unable to travel to Key West. Randy located a fantastic property on the island back in September 2019 at a very reasonable rate. The property looked wonderful and met all of our needs. When the crisis began, the staff maintained an open line of communication and postponed our final payment until there was clarity. I received a call from the owner of Key West Hideaways and found him to be friendly and he was open to a large number of options which would allow us to travel to Key West when the situation allowed. We opted for a refund. No worries! Kevin was understanding
Kaleen M.
May 03, 2019
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If you are planning a trip to Key West DO NOT use Key West Hideaways!!!! The vacation property rented was filthy . The sheets had black specks and the floors were so dirty that feet had to be washed any time one was barefoot. When approached for clean sheets , the property manager responded in a condescending annoyed manner. When a formal complaint was made to VRBO the property manager childishly responded by never acknowledging the complaint but providing a totally false review of the individual who rented the property. If you are looking for a reputable , most accommodating rental agency
Diana R.
Sep 29, 2018
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Victoria P.
Jul 28, 2018
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The Mermaid Cove is my absolute FAVORITE place to stay on the island. I love everything from the nautical decor, accessible location and comfortable beds! Our whole group felt so at home and welcomed from beginning to the end of our stay. The pictures don't do this little hideaway justice, you need to experience it for yourself! It was worth every penny, and I can't wait to stay at the Mermaid Cove again next year!
Holly V.
Jul 12, 2018
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So last summer July 2017, my husband and I decided we wanted to rent a home in July 2018. We went around to different companies and most places blew us off because it was a year away. Kevin at Key West Hideaways was more than willing to help and showed us two open properties and made suggestions on the ones that were booked. A year later, here we are renting a property and I have to say Kevin is amazing. Could our property be better? Yes, but I knew that I was renting a house built in the early 1900's and everything that could be unpleasant was laid out for me. It had nothing to do with
Katherine M.
Mar 31, 2018
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We loved loved loved Key West Hideaways! From the minute we booked they were super accommodating. They worked with us during the hurricane and let us reschedule. We stayed at the Secret Courtyard which had a great new trex deck, hot tub, and every other amenity we could need. They location was superb... walking distance to everything! And on our way our we met the owner who was fantastic. Highly recommend!
D. C.
Apr 15, 2017
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Kim M.
Nov 05, 2016
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Karen S.
Nov 04, 2016
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This was our (8 women) first trip to Key West and very much anticipated. We booked a rental that would accommodate our large group and also have nice amenities. We loved the place, but after the first night had a maintenance issue. Kevin at Key West Hideaways was "Johnny on the spot" and addressed our issue immediately. In fact, when it could not be corrected easily he moved us to an even nicer place at no extra charge to make sure we were comfortable for the entirety of our trip. I've never experienced such wonderful customer service as we did with Key West Hideaways. We&apos
Denise Terry
Nov 25, 2015
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We stayed at Royal Escape in July of 2015 and had an amazing experience. The house was clean and perfect as we had two families. There was plenty of room and the apartment/house combo was great for two families. Would definitely go again. The only thing we didn't love was the pool is a bit rough on toes and the deck is mighty slippery when wet and gets extremely hot, so be sure to bring and wear water shoes. We really enjoyed the outdoor dining space. The area was close enough to Duval for walking, but far enough away to enjoy some down time and family time. The hot tub was a bit temperamental
Cannon H.
Apr 04, 2015
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Mermaid Cove was a great place to stay. A quaint 4 room house all separated by a courtyard. Great food very close by. Right down from the southernmost point and the beach. The owner was by far more than accommodating to anything we needed and since he had time he offered to give us a ride to the airport. You will be more than pleased if you stay here. I will certainly stay here again.
Dan L.
Mar 15, 2015
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We stayed at 1219 Duval St, the "Mermaids Cove" and had a great experience. We had a group of 12 and never had an issue - the place easily slept all 12. Maintenance was very helpful in fixing an air condition problem and helping us move out efficiently.
The space is also incredible. The set up is essentially 3 cottages (One with an upstairs and downstairs that are entered from different doors, so a total of 4 unique keyed living spaces) that all open up to a spacious common patio area with a table, washer/dryer, and shed. The area is great for hosting and is great for large groups, as
The space is also incredible. The set up is essentially 3 cottages (One with an upstairs and downstairs that are entered from different doors, so a total of 4 unique keyed living spaces) that all open up to a spacious common patio area with a table, washer/dryer, and shed. The area is great for hosting and is great for large groups, as
Maria S.
Dec 29, 2014
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Friends of ours have used Key West Hideaways for the last two years with great results. This year, my husband and I accompanied them and another couple for a relaxing mini-vacation at Royal Escape. Perfect when you need plenty of space - and a bathroom for every bedroom - Royal Escape is located in Old Town, about a 10-15 minute walk from Duval Street, or a 5-10 minute walk to the ocean.
I loved the heated pool and the jacuzzi, and the large open-air dining table outside on the large patio. Even though each bedroom has its own bathroom, everyone's favorite place to get clean was the outdoor
I loved the heated pool and the jacuzzi, and the large open-air dining table outside on the large patio. Even though each bedroom has its own bathroom, everyone's favorite place to get clean was the outdoor
Fozia S.
Jul 23, 2014
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I have used keywesthideaways.com for many years. Being born and raised in Miami,Fl traveling to the keys is on the weekends is what you do.
I have to say my last stay, I booked through keywesthideaways. Our unit was on Amelia Street off of Duval. The room was more then I expected...however I needed a grill and Kevin the "after hours" call person responded to my request.
Kevin, exceeded my expectations! The customer "service" experience he gave to me and my family is priceless.
Simplicity does matter!
I have to say my last stay, I booked through keywesthideaways. Our unit was on Amelia Street off of Duval. The room was more then I expected...however I needed a grill and Kevin the "after hours" call person responded to my request.
Kevin, exceeded my expectations! The customer "service" experience he gave to me and my family is priceless.
Simplicity does matter!
Tanya C.
Nov 27, 2012
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First time to the Keys. I was online for hours searching for a great place to stay at for 4days. After reading several reviews about Key West Hideaways I knew it would be the perfect location for a group of 6 to stay. I decided to rent the Cuban Paradise. It has 2 bedrooms and two restrooms. A spacious living room, dining room, kitchen and best of all a patio over looking Duval St.
Upon arriving we had to check in at the main office. Service was awesome. I forgot the name of the two gentlemen helping me out but it was smooth and quick. They gave me all the information I needed and in less than
Upon arriving we had to check in at the main office. Service was awesome. I forgot the name of the two gentlemen helping me out but it was smooth and quick. They gave me all the information I needed and in less than
