Holiday rentals with a pool in Cudjoe Key

Casa loca was Absolutely beautiful! So close to everything in the keys. Host super friendly and helpful. The house was very clean! 10/10 stay LOVED IT!

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

This place was an absolute dream! The location felt so private yet was so close to whatever we needed or wanted. The house was very clean and so welcoming. It was just the two of us for this trip but with each of the 3 bedrooms having their own full bathroom, this place could have easily accommodated more. We definitely want to come back again with friends/family. The rest of the home is cozy and has everything you need. The outdoor areas are so nice and peaceful. The landscaping, private pool/spa area, and the fire pit area make it feel like you're in your own tropical paradise. The neighborhood was quiet and the people we interacted with were very kind. Seeing the Key deer walk around the area and hearing the peacocks made this place even more magical. This was our first time in The Keys and definitely won't be our last. The worst part of this experience was having to leave. This lovely place definitely made it difficult to go back to real life. We can't wait to come back!

We had a great time at Judy’s airbnb. It was super nice, clean and had really comfortable beds. The pool was right across the parking area, very clean, private and always had chairs available. Over all our stay was great and we will definitely be back.

We thoroughly enjoyed our stay at the Catherine house and it was a perfect location to explore Key West. Beautiful space and well thought out. Perfect for two couples! A welcome retreat when you wanted to get out of the Key West hustle and bustle. We loved our time there!

We had six adults in our group and the house was a perfect location to go out fishing or to the beach. The house was well stocked and with plenty of linens and beach towels. We rented a boat for three days from Tropical boat rentals and the canal location made fishing super easy. Access to the ocean or the bay was convenient. We even caught several fish in the canal. We saw manatees, sharks, manna rays and tons of fish while enjoying the swimming pool. We can’t wait to make a return trip.

It really is the perfect place to stay. We picked this house after our last trip to FL where we rented a beach house only to have high winds and man of war jellyfish so couldn't get in the water at all. This place with its amazing hot tub and pool, tons of pool toys and floaties, books and games, would be a wonderful vacation even if you were stuck there the whole time due to bad weather, These owners have done a wonderful job thinking of so many amenities- cozy couch blankets, life jackets, tons of beach equipment, so many dishes and pans and various drink holders. The only complaint I could think of if I had to would be to have another ice tray (there were two semi broken ones but not a big deal as we just bought ice). But that's a pretty small thing in the long list of things that were superb. Even the beds were as soft and as comfortable as mine at home. I hate to let the secret out, but this house is fantastic.

We had an amazing time! The location is perfect with so many things to do, pool, hot tub, canal, etc. The home was overall beautiful and we loved every second of it!

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!

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.

Beautiful condo right on the waterfront within Truman Annex! Fully renovated with every amenity and matched the photos exactly. Multiple balconies were great for morning coffee or afternoon tea, and the location is incredibly convenient with a coveted reserved parking space in the parking garage. We highly recommend not only the condo but Last Key’s concierge Alena!!! Everything was perfect and she made the process incredibly smooth from check-in to local recommendations. We will absolutely stay with Last Key again!

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.

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!!

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.

We were comfortable here. It was easy to find and parking was always available. It was quiet except near the airport, but it wasn't disturbing. There were plenty of towels and a washer and dryer, which were convenient.

Great Place! Everything was so easy from booking to checking out. Jennifer is very communicative, gives clear instructions and responds in a timely manner. The home is clean, comfy, has a very nice view, and we enjoyed sitting on the balcony and listening to the music from the restaurant down below (don't worry, the music stops at a reasonable hour). The downtown area is close enough for us to ride bikes. Publix grocery store is close by too. If we're ever back in Key West, we wouldn't hesitate to stay here again.