USA Florida Key West Old Town Key West Listing #10787

Poolside Paradise - Key West, FL

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44 reviews
Max. occupancy: 10 1 King Bed, 2 Queen Bed, 2 Sofa Bed 3 bedrooms 2 bathrooms 4 dog max  (40 lb weight limit) 
Address provided after booking

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Expert cleaning

Pro housekeepers clean thoroughly and provide fresh linens before every stay.

Local support

Count on 24/7 guest care and local teams everywhere we operate.


Smart locks or lockboxes at many homes offer smooth, contactless check-in.

Cute, updated Key West home w/ private pool - close to Duval Street, dogs ok!

Bring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, a private pool, a furnished patio, two full kitchens, and off-street parking for two vehicles (a real rarity in Key West). And dogs up to 40 pounds are welcome for a small nightly fee.

This home is located one block from Duval Street, the most popular street in all of Key West, where you'll find fantastic restaurants, unique local shops, and year-round special events and festivals. Play on the sand and people-watch at South Beach, just a half-mile away. Visit the many historic sites including the Ernest Hemingway Home & Museum and the Key West Lighthouse, both only a couple blocks from your front door, as well as the Truman Little White House and the Mel Fisher Maritime Museum, just under a mile away over on Front Street.

Ideal for an extended family or a few couples traveling together, this home offers free WiFi, four cable TVs, two full kitchens, and a private swimming pool located in the enclosed backyard. Fire up the gas grill and enjoy a family cookout on the furnished patio, or just settle back and enjoy the sunset.

Choose this adorable vacation rental for your next big trip to the Southernmost Point.

A damage waiver, covering up to $2,000 of accidental damage to the property or its contents, is included in the cost of your reservation.

Parking Notes: Off-street parking for two vehicles is available.

You must be 25 years or older to rent this property.


Heating & cooling

Central AC

Partial AC

Kitchen & dining





Internet : Comcast



On-site activities

Pool : Private



Beach towels



44 reviews

Ashley O. May 2021
We loved the location of this home on Olivia Street! Close enough that we were able to walk to Old Key West and visit the Southernmost point, but we could also walk all the way down Duval Street to Mallory Square. The accommodations were comfortable and Vacasa was good about an early check-in and late check-out. Would highly recommend staying here if you have a group on the larger side.
Angela F. May 2021
The pool was just the right size to cool off after lunch! Location is perfect!
Chris D. Mar 2021
This house is in the perfect location just off Duval Street. Its close enough to walk to everything without being kept up at night from everyone walking by. The house was clean and fit 8 of us perfectly without being overcrowded.
Chelsea D. Dec 2020
This location was awesome! The pool was very cold and I wish there would have been more common household items in the kitchens. Other than that, the place was fun and clean. Perfect location in Key West!
stephen s. Oct 2020
This place was excellent. The house was clean , the pool was perfect and the beds are actually comfortable. The house is next to everything and right off Duval street. 8 of us slept there with plenty of room to spare.
Brandon S. Jun 2020
Loved the stay. Great location steps from Duval St and all the great bars and food they have to offer. It was nice staying in the pool and just relaxing after being out all day long. Would highly recommend to anyone and will def be booking another stay at some point.
Mary Pat P. Feb 2020
Manager was extremely attentive to the few issues we had. Place was very clean. The only thing I would suggest is washcloths and some towels were very rough!
Leslie H. Jan 2020
Location was fab. Two house set up was really good for us.
Crystal B. Jan 2020
We enjoyed our stay at Poolside Paradise. We rented both sides of the home to accommodate 8 people. The space and pool area were great and we walked to everything. This house is in a great location and comes with everything you need.
Joshua J. Jan 2020
We rented these two units the week of New Year’s Day. We really had a great time. Two very good units.

It wasn’t clear to me when we reserved them that the two units share the pool, deck, washer/dryer, and outdoor grill. I’m glad we rented both. It gave us plenty of room and privacy. I could see the two units being a good choice for two families with mixed age children or multigenerational families vacationing together.

The location is ideal: one block from the quieter end of Duvall Street. While this makes getting to bars, restaurants, and many tourist attractions like the Little White House, Lighthouse, and The Hemingway House an easy walk. On the other hand, Olivia St. does get a good bit of thru traffic and unit closest to the street can be a little noisy - once again, it was the week of New Year’s Eve.

The kitchens are equipped with most of the basics you’ll need to prepare meals and mix drinks, and there is a good grocery store on Fleming just a few blocks away (Fausto’s).

It was great to have a pool, outdoor grill, and washer/dryer. Every room has a TV with Cable. The pull out couch in the main room is a bit old and saggy, but I would imagine it would be helpful if you needed the extra beds. That room could also use a larger TV given the size of the room and the location of the TV.

All in all, two very good units. We’d likely reserve one or both of them again.
Patrick M. Oct 2019
Short walk to all the attractions. The pool is amazing. The house has so much room!
Donna B. Sep 2019
Great location only 1/2 block to Duvall St and 3 blocks to Hemingway's home. Private Pool. Comfortable beds. Clean.
All linens provided and paper products! Quiet Neighborhood
Jacquelyn B. Jun 2019
Location, location
deborah b. Jun 2019
The home, pool, and bedding were clean, in a fantastic location, and parking area was great! The people were friendly and sent help quickly when the air conditioner wasn't working.
kevin t. Jun 2019
Very nice place to stay
Heather S. Jun 2019
This was a wonderful property for our large family. Would also be great for a large group of friends. This is two properties together. We rented both. There is a great little pool in the middle and parking for two vehicles. Pool is a great gathering spot. Duval Street is steps away and you are within walking distance of the majority of sites.
Kim P. Jun 2019
Loved the location, clean and comfortable.
Cindy N. Apr 2019
We rented both units in this house-they weren’t overly spacious, but just the perfect amount of space that we needed. We only used one of the kitchens and it was equipped well. We spent most of the time outside next to the pool-or in the pool, which was great after a day out exploring! The house location was great, central to most everything, so we were able to walk most everywhere. We all just really enjoyed our stay there!
Judith H. Apr 2019
That the House was real close to Dival Street.
Rachel D. Mar 2019
This is the second time our group of 10 has stayed at this property. The first time it was managed through Key West Vacations Rentals. We enjoyed our experience more when it was managed through a small company who valued detail and customer service. KWVR offered a courtesy shuttle to and from the airport which is no longer available. We had a difficult time obtaining the local number for vacasa. Every time we called we spoke with someone from Across the U.S. which was frustrating. In terms of the property, it is run down, needs a fresh coat of paint and new fold out couches. We realize this is a rental but the lack of upkeep is unacceptable. It doesn’t look like it’s been fixed since we stayed two years ago and mentioned the same issues. We called Vacasa regarding our broken grill and unheated pool. While vacasa was responsive, it took two days and a few phone calls to have the issues resolved. Prompt resolutions to maintenance issues is important when you’re only staying at a rental for a short time. We were then told that it costs $5/day to heat the pool and we should of called 3 days prior to our stay to set that up. This should of been advertised on the website or communicated to us. Maintenance did come to fix the pool but unfortunately told us the heater had a leak and could not be fixed during our stay. Believe it or not, our group is much easier to please than most. The lack of cleanliness (stained sheets, dirty floors and couches) would of put other groups way over the edge. My friends and I have been loyal KWVR customers and will not be renting from Vacasa next year.
Christie W. Jan 2019
We rented both units and it worked great for us. We had plenty of room for 7 people. There is a little bit of road noise but otherwise was great! So close to be able to walk everywhere. Only complaint was one window wouldn’t lock & a door wouldn’t deadbolt which made a group of 7 women a little nervous but worked out fine!
John E. Jan 2019
Location was perfect...close enough for access to most everything but just far enough away from the main traffic/noise. House was only serviced once in 6 days but to be expected with a house vs hotel. Also did not realize this was a duplex when booked but since we had both units didn’t really matter.
Erik A. Dec 2018
Great spot in a great location just steps from Duval. Highly recommended.
Julie & Amanda J. Oct 2018
I think the best thing about this house was the location. It is walking distance to Duval, yet far enough off to have quiet (except for the roosters in the morning). It is also nice that it is two separate places in case some people need quiet/space for themselves. There aren't many places around with a pool either. We were supposed to have 10 people in the house, but ended up with only 6. I think if we had 10 people it would have been pretty cramped, but it is doable.
AARON B. Sep 2018
Great little cottage in the heart of it all! Pool was great, a little tight for 7 grown men on a bachelor party but all amenities worked out well. If you wanna nice spot right off of Duval for Bar hoping this is the place.
Nancy S. Jul 2018
The only negative to this rental was the noise on the roof. Sounded like an animal was up there. Lots of knocking sound.
Manager response:
After some investigating we discovered there was a tree branch scraping the roof. This has been trimmed back, and we appreciate this guest letting us know about it.
Scott S. Jul 2018
Close to everything. Clean home but beds and couch need supports replaced.
Also great pickup and drop off services.

Manager response:
We are very sorry we did not realize the sleeper sofas were broken. We have just ordered new ones. Thanks!
Lori V. Jun 2018
The location and convenience would make any flaws forgivable but I don't have any criticisms at all. This was perfectly comfortable for our group of 9 for four nights. We walked just about everywhere but still enjoyed being able to park two cars off the street so that we had them for the occasional longer jaunts. The shared deck and pool served as the perfect gatherings spot for the group. Can't tell you how great it was to have the pool to bounce around in when you come back all sweaty and hot from shopping and whatnot, and it gave us something to do while people cleaned up in shifts between the two bathrooms. We didn't grill or cook, but all of the tools where there. Housekeeping came daily, which was great. The AC worked fabulously and even the sofa beds weren't reported as being uncomfortable. If I came back with a group, it would be hard to convince me to look elsewhere.
Melanie M. Jun 2018
This house worked out great for a couple families to see the lovely Key West. The location was wonderful. Can be loud at night but that's to be expected in this town. We thoroughly enjoyed the pool. I appreciated the clean towels, toilet paper, and parking spaces. The only thing preventing a 5-star rating from me would be that the mattresses are past their life (big dips in the master bed caused me backaches everyday and my children could feel the bar under the sofa pullouts). Having access to the washer and dryer would also be a huge plus, though I understand it was not listed as an amenity. Overall, it worked out fabulous to eat a number of meals at the house and to use it as our home base.
Alishia N. Apr 2018
This house checks the basic boxes for a quick trip to Key West - kitchen, multiple bathrooms and bedrooms, and good location. The staff at the main office were very helpful and accommodating. It was wonderful to have a free shuttle to and from the airport. However, if you were looking for a little more comfort, you may be disappointed in the pullout couches and lack of updates to bedding. It worked for our crowd of 7 for only 3 nights, but anything more would just not work. Overall it is a decent place for a weekend getaway.
Ann C. Mar 2018
Great location to Duval Street. Home was very relaxing and cute. Management was very friendly and maids were great. I would definitely rent their again.
Lawrence S. Mar 2018
Great spot. Easy to get to. Very comfortable. Great pool.
Nora P. Jan 2018
Bathroom and Kitchens are nicely updated. Place was clean and very close to Duval St.
Furnishings need updating- pullout couches are dated and no longer comfortable.
Staff, Pool Mand and Cleaning lady were all very nice!
Neighbor is not friendly and blasted music starting at 7am, all day long.
Anthony I. Dec 2017
My friends and I really enjoyed our stay at Poolside Paradise! This is our 3rd time staying here and we love the location and everything that is offered with the house. We will definitely be back!