Key West is home to the southernmost point in the United States, and it’s a popular vacation destination for those looking to enjoy the island’s many draws. Because this island is so small, it can be hard to find affordable and unique accommodation. Here is a list of different Vrbos in Key West, Florida. There are different amenities and features for all budgets, so there is something unique for every traveler!
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on March 13, 2023.
1. Cozy room rental with a private pool (from USD 99)
Take your special one on a romantic getaway to this cozy room rental located just a few minutes from the beach. This open-plan living space has a queen-size bed, one full bath, and a compact kitchenette with basic tools and appliances to easily prepare delicious meals. There is also a table for two across your bed and a flat-screen TV for your entertainment.
One thing that you will love about this place is the private pool that you can enjoy during your stay. There are also some sun loungers beside where you can relax and get tanned.
Top guest reviews
Amenities & Room:
it would have been perfect if the wifi was stronger at the poolyou do need to bring your own coffee pool is good for a dip rather than a swimken has thought of everything: beach chairs pool towels umbrellas in case it rains and our favoriteCleanliness:
the room is very clean and has everything you needthe room was clean and ready when we arrivedthe place was clean and we could walk to our favorite spotsthe room was clean and not too far from the best places in key westHost:
ken was a great hostken was very gracious owner and helpful throughout2 bikes ken is an excellent host and a great communicatorthe owner was responsive and accommodating and the property was in a great locationRead more reviewsLocation:
loved the location of this propertygreat rental in a great locationperfect location and size especially as we were always out and about
2. Pet-friendly studio rental with a porch (from USD 198)
Pack your bags and head to this charming studio in Key West to enjoy a sunny getaway. This living space is ideally located close to the beach restaurants, shops, and vibrant nightlife. It houses one king-size bed that sleeps two guests comfortably, a seating area that can also be used for dining, and a kitchen that is complete with modern appliances for you to make delectable meals.
There is also a covered porch with a table for two where you can have morning coffee together or grab some drinks at night. This property allows pets for a fee of 90 USD, so your furry pals can tag along.
Top guest reviews
Amenities & Room:
The bed was comfortable and the place was just the right sizePam was easy to contact and provided great advice on places to see and things to doWe brought stuff to cook for some meals and used the kitchen for most breakfasts so we could splurge on lunches and dinnersThis cute little place had everything anyone would need while vacationing in Key WestThis studio unit is very well appointed with lovely king bed nice bathroom and has fully equipped kitchenHost:
really all you need Decorated cute and close to many things including Duval St (very close)The Simonton Studio was absolutely perfect for usProperty manager was very easy to communicate with and very helpfulWalk to Duval Street and all it has to offer Definitely will be backWe stayed in Simonton Studio for our honeymoon and absolutely loved itRead more reviewsLocation:
But the LOCATION was perfect Walking distance to just about everythingThe location is great for walking or biking everywhere plus is on same street as free bus loop around town Also went to several amazing restaurants in the immediate area for dinnerit did not disappoint Lots to do just walking/biking distance from property- Pam provided tons of info too which was so greatThe bikes were a huge plus You could walk or bike anywhereThis was our first time in Key West and this location was perfect and central to everything
3. Charming retreat with a plunge pool (from USD 560)
This charming home is your gateway to a relaxing getaway in the Keys. It’s great for families or small groups of friends looking for a comfy place to stay close to some major attractions. The renowned Duval Street, for instance, is just within walking distance from the property, and it’s where you can find some of the best shopping, dining, and entertainment spots in the region.
Puerta Coralina, as the property is called, is big enough to accommodate a group of up to six. Interior areas include two bedrooms, a living area, three full baths, a dining area, and a kitchen—all fully furnished and equipped for guest comfort and convenience. The outdoor areas, on the other hand, include a beautiful front porch and a fenced backyard with a furnished deck and a plunge pool.
Top guest reviews
Amenities & Room:
pool was warm which was perfect for cooler weather great lounge chairs upstairs and on the back porchand the back deck and pool were wonderful to return togreat tvs and wifi to enjoy the olympics when we weren’t out and aboutwe enjoyed its outdoor areas too including the pool patio front porch and upstairs deckCleanliness:
great location very clean and plenty of roomHost:
the property manager was responsive quickly to our needsRead more reviewsLocation:
centrally located in key west and in easy walking distance of all our favorite spotsit is in a great location if you plan on exploring key westlove this place super quiet neighborhood house is very comfortablewonder property location and manager was great
4. Cozy abode with views of Truman Waterfront Park (from USD 440)
Perfect for couples or small groups of friends looking to have a relaxing vacation, this fully furnished home is a comfortable accommodation for Key West visitors. This rental features a private balcony that provides a stunning view of Truman Waterfront Park. It can comfortably sleep up to four people via its two bright and spacious bedrooms. The kitchen comes with all the essentials to ensure easy food preparation.
Its location is also great as you’re a short stroll away from Duval Street, the world-famous commercial area where you can find lots of dining, shopping, and entertainment hubs. Fort Zachary Taylor Historic State Park Beach is also just a few minutes away by foot or bike, providing easy access to beautiful sceneries and lots of outdoor recreation.
Top guest reviews
Amenities & Room:
the bedrooms had mirror sliding doorsThe kitchen had everything we neededWe did take Lyft one night for our anniversary because it was so hot and humidThe plants and flowers in the courtyard are beautiful and makes you feel like you are secludedCondo was immaculate Washer and Dryer in condo and easy to use Fastest WifiCleanliness:
It was decorated very nicely and very comfortableThe house was very nicely decorated and included everything we neededThe common pool was heated in Dec which was greatIt is very comfortable and cleanlocation is great rental is clean and comfortable and enjoyed the poolHost:
We were super close to Duval street with all the good attractionswas very easy to help and answered any questions we had One suggestion--move the bathroom mirror down some It works for tall people but not for us petite onesThe pool is was very nice and refreshingEveryone we talked to in the community was very friendlyHighly recommend this rental Unit was very clean well stockedRead more reviewsLocation:
It is within a few blocks of Duval Street where a lot of restaurants shopping and bars areYou can walk to shops restaurants and of course the barsVery close walk to everything while still far enough for peace and quietnessthere was a playground 3 min away and Duval street is only a few blocks awayCondo is close to everthing we walked 95 percent of the time
5. Lovely paradise with a private pool (from 880 USD)
This lovely home is named after Ernest Hemmingway’s fishing boat “Pilar,” and it truly is a secret paradise. With three bedrooms and three bathrooms, it’s great for families and large groups. The living room has wide doors opening to the beautifully decorated backyard. There is a private pool, hammock, and outdoor seating perfect for entertaining guests. Though located in a quiet gated community, this house is within walking distance of Duval Street and other attractions.
Pilar's Secret
Price: from 880 USD
Number of Guests: 8
6. Colorful oasis with a lazy river pool (from USD 400)
This home is picturesque Key West style, and its bright colors are perfect for a happy vacation in this island paradise! This house even has its own heated lazy river pool for relaxing! The Old Town Key West enchanting garden home is located in one of the last remaining authentic Old Key West neighborhoods, and it’s walking distance from the Hemmingway House and Duval Street. Live like a local in this charming Key West vacation rental.
Top guest reviews
Amenities & Room:
what a delightful bungalow full of old world charm but with modern plumbing and wifi and comfy new bedsat night the lit pool was relaxing and sereneHost:
susan is a super hostonce you meet your host susan you will fall in love with hershe is very accommodating quick to respond and simply a delight to work withwe quickly fell in love with john's bungalow and the owners (susan and bruce)we can't say enough about the owners susan and bruce who now are dear friends of oursRead more reviewsLocation:
the location is fantasticthe property is centrally located within walking distance of all of old town restaurants and entertainmenti love this spot great things to walk / ride bikes to nearbythis is a wonderful home located on a quiet street near all the excitement of key westit was close to many attractions and restaurants yet very quite for some down time
7. Stylish hideaway with a backyard (from USD 150)
This Old Key West style conch house has shining reviews and promises to be the perfect getaway location. With a stunning backyard featuring a large private pool, this house is a bargain find. Located only a block from Duval Street and within walking distance of the Hemmingway House, it would be hard to find a better place to stay on the island.
Top guest reviews
Amenities & Room:
the place was great with a very private pool area in the rearCleanliness:
the house is clean the pool is beautifulthe inside is quaint and clean the pool is absolutely fabulous and the rooms are privatetree tops is adorable clean exactly as pictured and decorated with local art workHost:
owner was very helpfulthe owners and neighbors greeted us and made us feel so welcomethe property is one of a kind and sheryl is great to work withsheryl was extremely helpful and easy to work withRead more reviewsLocation:
the neighborhood is very quiet and easy walking distance from duval stit is in the best location and has everything you need for the perfect key west locationgreat location and perfect for a groupthe location is one of the best and easy walking to duval and many great resturantsthe place is a little piece of paradise inside of paradise
8. Beach-themed condo with a shared pool access (from USD 660)
This two-bedroom condo is an ideal stay for a family of six and is just a few steps from Ernest Hemingway Home and Museum and Duval Square Mall. When you enter the living room, you’ll be greeted by the cutest beach-themed decor and furniture. Slowly sip on your coffee and take in the view from the deck. The rental comes with central air conditioning, a flatscreen television, and free Wi-Fi. You could also swim a few laps at the shared pool and have a picnic with your loved ones at the gazebo!
Top guest reviews
Amenities & Room:
pool is shallow but great for a hour or two rest in the afternoonCleanliness:
very clean and lots of spaceproperty was clean and well maintained including the poolhome was clean and well furnishedgreat accommodations unit was exceptionally cleanthe townhouse was clean with very comfortable bedsHost:
we enjoyed the propertyand the staff are all friendlyRead more reviewsLocation:
location is good being fairly central making everything within walking distancegreat location on duval streetwalking distance to major attractionslocated in a great location we felt safe and secure in this comfortable town homeperfect location very secure and a wonderful place to stay
9. Unique houseboat best for couples (from 180 USD)
There are perks to vacationing on a small island, like being able to stay on a one of a kind houseboat. The Stock Island Marina houseboat is a one bedroom one bath condo, perfect for couples or small families looking for a unique way to stay on Key West. There is also an on-site restaurant and a complimentary shuttle service to downtown available for all guests.
Stock Island Marina houseboat
Price: from 180 USD
Number of Guests: 2
10. Well-located haven with oceanfront views
In case you wish to escape from the busyness of Key West, Oceana Vista offers you a reprieve from the comfort of Bay Point. Bay Point is a short 10 miles (16 km) north of Key West and offers peaceful island life. This Oceana Vista rental allows you your own slice of paradise, with 1.5 acres (0.6 hectares) of beachfront views.
Oceana Vista
Price: Depends on dates
Number of Guests: 10
11. Old Town luxurious abode with a private heated pool (from USD 786)
If you’re traveling with a large group and need a lot of space, this Old Town luxurious home is a great find. With four bedrooms and three bathrooms, this large home will fit up to eight people! There is a private heated pool in the backyard, and it is within easy walking distance of all the best attractions like the beach and Duval Street.
Top guest reviews
Amenities & Room:
plenty of space at the dining table and the towel supply was great toovery comfortable for 3 couplesCleanliness:
close to everything very clean bright and airyHost:
owners were easy to reach by messaging through the vrbo appallison was very responsive to questionshome owner found this property available for us the staff at compass realty was accommodating helpful and friendlyshe was always very responsive and timely in getting back to us with any questions we might haveRead more reviewsLocation:
pool onsite was great perfect location close to duval and many attractionsgreat location nicely suited for families with childreneasy walk to state park for great sunset viewingthis townhome is located very close to duval street and many local attractions in key westsuch a great location- private pool - close to duval- comfortable bed- everything you need and more
12. Victorian condo with city views (from 180 USD)
Located in a turn of the century Victorian Condo dating back to 1868, this condo in the heart of Old Town Key West is an amazing find. With the ability to sleep four, enjoy the luxury of being close to everything. This condo also has a beautiful wrap around outdoor porch for quiet nights overlooking the city.
The Coral Condo
Price: from 180 USD
Number of Guests: 4
13. Deluxe sanctuary with a pool and a waterfall (from USD 1151)
This vacation rental is the epitome of Key West living. Tucked away in a quiet neighborhood not too far from the busy Duval Street, this home promises an authentic local experience. The living room has a beautiful view of the outdoor space, complete with a waterfall into the pool and an outdoor shower. Experience Key West as a local in the Southard Comfort.
Top guest reviews
Host:
we met the owner who was so friendly and accomodatingrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulthey were very helpful with checking in and making sure we were ok over our stayRead more reviewsLocation:
location was superb as welleasy access to the free duval loop bus was a plusplenty of room for six adults and the location made for an easy walk to duval streetthe house was in a good location and was as picturedperfect location and very quiet and relaxing after being in main section of town
14. Top-floor condo with ocean views (from USD 542)
This spectacular penthouse condo, also known as Paradise Found, sits on the topmost floor of a residential building. It’s newly renovated and can comfortably accommodate up to six guests! Enjoy the spacious and comfortable bedrooms at this flamingo-colored condo, which is just a few steps from the waves and fine sands of Smathers Beach. Paradise Found’s close proximity to all that Key West has to offer makes it one of the most sought-after rentals in the area. Book your stay now.
Top guest reviews
Amenities & Room:
nice view of ocean and pool from large balconythe wall unit in the living room was our favoritethe pool and hot tub are amazingour family loved the condo the pool was beautiful and the grounds of the property were gorgeousCleanliness:
condo was spacious and cleanclean up to date and safecondo was very clean with everything you need for an enjoyable vacationlocation was great condo clean and quietpool is amazing hot tub was always clean and working properlyHost:
a site map would be very helpfulRead more reviewsLocation:
just gorgeous comfy well maintained and the perfect locationthe location view pool and property maintenance and security are great
15. The Conch Farmhouse (from USD 389)
If you’re looking for style and a great location, look no further than this recently renovated Conch Farmhouse vacation rental in Key West, FL. This house has two beds and one bath and is only a two-minute bike ride from the beach! In addition, this Key West vacation home rental is centrally located near Duval Street and some of the best attractions, so you don’t have to worry about driving!
Top guest reviews
Amenities & Room:
also the ceiling fan in the four poster bedroom is off balance and makes noise when turned onwe had to choose to omit the fan and sleep in an 80 degree roomfabulous location clean and modern fully equipped from kitchen gear to beach chairscharming very much so not practical when you would like bathroom privacyCleanliness:
the place was clean and modernthe place was very clean and organizedlocation was great condo and grounds were very clean and quietproperty is attractive very clean well supplied and conveniently locatedthe home was immaculately clean very inviting and relaxingHost:
the owner was wonderful with timely responses to a few questions we hadthe owner was so accessible and helpfulthe owner did a fantastic job with communication and directions for parking etcRead more reviewsLocation:
awsome condo in a great locationvery beautiful condo in a great locationthe location was perfect within walking distance to duval restaurants “ftfirst the location was the best - convenient to old town and the amphitheatereverything one needs close to duval and interesting attractions but insulated from noise and traffic
Enjoy Key West!
The best way to enjoy Key West is like a local! What better way to explore this beautiful island than from your own Key West beachfront rental oasis? Though the island is small, it has a number of vacation rentals perfect for all group sizes and budgets! Once you’ve found your home away from home, check out the top festivals and seafood restaurants in Key West!
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