
Vacation rentals with a pool in Cudjoe Key
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Top-rated rentals with a pool in Cudjoe Key
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Popular amenities for Cudjoe Key rentals with a pool
House rentals with a pool

Gone Coastal
We enjoyed our stay here. It was an out a 20-25 minute drive to Duval so did have to take an Uber everywhere we went since we hadn’t rented a car. Overall it was a very nice place-we just weren’t crazy about the location.

Coastal Comfort; Waterfront Luxury Home with priva
We all loved the house. Plenty of space, the outdoor patios were a daily hangout, the views were great, what's not to love. The maintenance of the house itself was excellent and it didn't feel like a "rental". Well decorated, not worn down, a bathroom for everyone, it was great. We rented a golf cart to get back and forth from town which was very easy and barely a ten minute drive. We did have a small issue with the pool while there, which apparently is very unusual. It is Key West so it took a few days to get the parts needed. However, Javier was always easy to reach and while he did eventually fix it it was his 'out of the box' thinking and communication on everything that was superbly professional. I understand he manages several properties and we would gladly stay at any of them. With an AirBNB, if something goes wrong and you're far from home all you have to rely on is the owner/manager and you are in excellent hands with Javier. A++ on customer service

Waterfront House - 30' Dock & Pool & Cabana Club
We will be back! We loved it! Clean, comfortable with lots of room. We loved being able to keep our boat behind the house and the trailer in the driveway. We loved walking around Keys Colony. The Cabana Club and Sparkys Restaurant were both within walking distance. The kitchen had every gadget you could imagine. The dining table was perfect for dinners and card playing. The beds were comfy. No allergies whatsoever! Thank you so much!!

Pelico Palms Sunset Suites
fantastic cottage and pool with plenty of privacy, close to the water. basically 3 master suites with adjoining bathrooms, one living area and a kitchen. really big pool deck with seating and cornhole, Webber grill and outdoor dining table. (bring bug spray). we had a great time, close to key West and Bahia Honda, a great cottage!

P23 - New 3 bedroom 2 bath duplex with private po
Our stay was wonderful! Key Colony is a quiet and peaceful community. Our condo was beautifully decorated and had everything we needed for the first couple days. The sheets and towels were soft The beds were very comfortable. We really enjoyed our stay and hope to go back soon again!

Get Hooked private pool and dock
We recently had the pleasure of staying at a fantastic vacation rental, and it exceeded all our expectations! The house was comfortable, spacious, and perfectly equipped for a peaceful and relaxing stay. One of the highlights was the location—just a short and scenic walk to the beach, making it easy to enjoy the sound of the waves and the coastal vibe. We were also treated to the most beautiful sunrises each morning, a sight that truly made the experience unforgettable. The home was spotlessly clean, with thoughtful details that made us feel at ease. And Sheri, the host, was incredibly friendly and welcoming, ensuring every part of our stay was smooth and enjoyable. Her kindness added an individualized touch to the experience. If you’re looking for a perfect getaway with stunning views, a cozy atmosphere, and a host who genuinely cares, this place is absolutely worth considering!

Casablanca ~ Fabulous Home w/ Private Pool/Parking
The house is perfect! It’s very clean and has everything you need. The kitchen is fully stocked with plates, glasses, etc. The bathroom had a nice shower and plenty of towels. We love the location! We parked our car and never used it. You can walk everywhere. The backyard is amazing. The pool is beautiful. We swam every day and loved sitting in the yard relaxing. We will be back.

Gorgeous 3/2 SFH Brand-new pool&spa, 30ft dockage
We had a great stay. The backyard is absolutely beautiful and feels very peaceful. We were treated to four manatees as well as a nurse shark off the dock over the course of our week here! The pool and spa were great and as advertised. Heather’s home is incredibly well stocked- more than enough towels for the baths and pool and the kitchen had everything needed for cooking as well as a great dishwasher which was great for vacation. Although we did have some issues with the property after check-in, the property host, Katie, was immediately available and very responsive to our concerns, and we were more than happy with the outcome. Would stay here again.
Condo rentals with a pool

2 Bedroom Oceanfront Complex Heated Pool KCB
We had a great time! Awesome community with walkable restaurants and bars. We loved the local beaches. The people at the complex were super nice. Our four boys loved running from the pool to the beach. Everyone we met was very nice. Great instructions and recommendations. Loved it!

BOOK today and enjoy our amazing discounts for yo
We had a great time at Julia's place! The condo was beautifully furnished and we enjoyed pool and private beach area. We love to walk and the location was perfect for us! The nearby deli and restaurants were also very good. Ubers are very quick and reasonable.

Oceanfront 3 bed condo Ocean Edge w/ optional slip
Carrie's place was absolutely beautiful! it was so clean, the beds were insanely comfortable, and there were tons of linens and towels for everyone. We very comfortably fit 8 people into the home with no problems. The view from the balcony is absolutely amazing and we were all blown away. Carrie was extremely responsive and friendly. We were here for our wedding and had our wedding party stay here so it was extra magical. The pool and hot tub is super close, elevator to help with our bags, and the resort itself is gorgeous. 10/10 would stay again. We loved it so so much! Don't miss out.

Top floor Ocean Views, Spacious 2 Bedroom Condo, V
This was our first time in Key West. We wanted to stay a little tucked away from the downtown bustle. The complex is beautiful with great amenities. And it’s close enough to shopping, restaurants and bars! We definitely plan on booking the same place in the future!!

Tropical Escape at Sunrise
Eric’s place was lovely, well maintained, nicely appointed, and immaculate. The 3 of us enjoyed the balcony overlooking the pool. Even though the apartment is near the airport we only heard planes twice in the 4 days we were there. There is a convenient little grocery store on the site and excellent BBQ from a food truck near the pool. Eric responded to our questions promptly. Comfy beds, everything worked and we enjoyed our stay. Would stay here again.

Promenade to Paradise at The Annex
Absolutely fantastic unit and location, and the communication and service from Last Key was white glove. Top notch. We will be back.

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access
A very well appointed condo with everything supplied. A great view over the marina. However, close to a main route into Central Key West made it a slightly noisy location. Also next door to a bar/restaurant,this made sitting on balcony a not so peaceful experience. For those interested in watching TV the wifi was awful. The pool area was predominantly in the shade come the afternoon. The host was very responsive and helpful. All in all, we enjoyed our stay as we loved Key West.

Fully renovated 2/2 bath condo w/ shared pool!
We had a great stay at Chris’s place in Key West! The property was exactly what we needed for a relaxing getaway. Chris is an excellent communicator—his instructions were clear, detailed, and made everything super easy from check-in to check-out. We felt well taken care of and really appreciated the smooth experience. I’d definitely recommend this place to anyone planning a trip to Key West!
Quick stats about vacation rentals with a pool in Cudjoe Key
Total rentals
210 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
4.8K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
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