Waterfront vacation rentals in Cudjoe Key

I had an absolutely incredible experience! From start to finish, everything was flawlessly organized, making the journey to the location a total breeze. The host was incredibly welcoming, instantly making me feel right at home. This was precisely the getaway I had been craving for my three-night escape! I'm already counting down the days until I can return! Without a doubt, I’ll be sharing this hidden gem with all my friends and family!

Condo was great. Exactly as described. 2 minute walk to the large heated swimming pool and beautiful ocean view. Shuffle board and ping pong available to play near the pool area. Safe, quiet, gated condo community. Within short driving distance to many great restaurants and activities. Frank responded within hours and answered my questions. We would recommend this rental and would gladly stay here again!

Very nice condo in key colony beach, affordable, great stay for a family. Clean rooms, nice pool, nice private beach area, will bring family down again.

We had a great stay in Islamorada at this house. Location is perfect! We were minutes away from so many things. My daughter loved looking for all the little lizards that scattered as we entered the patio. The house was well stocked with things we needed. Beach stuff wise, there are noodles and some camping chairs - no kids sand toys so plan to bring those if you have little ones. There were 4 beach towels provided. The washer was broken while we were there so hopefully it is repaired soon. Of note, the mattresses are very firm so if you like a softer mattress then it might not be the house for you. Also, if you happen to find a man’s ring in the house, it might be my husband’s. Please let the host know so we can arrange to get it back.

It was the perfect location that we wanted away from a high tourist area. The neighbors were very nice and welcoming. Everything was clean and beautiful. I would stay here again! It was perfect for us exploring both the southern and northern keys and beaches since it's about middle of the 2. Loved it!

The Condo was spacious, beautiful, well furnished, very clean and the location was perfect. Henry was great to work with. We rented a golf cart and traveled almost everywhere in Key West by golf cart.

We (two couples) enjoyed a great week here. Being on the canal was nice, outside sitting spots were great. The house had plenty of cooking supplies needed. Was a tad bit smaller than I expexted, but worked out just fine. Remember to bring your shampoo, body wash etc as it's not provided. Comfortable and bright, was quiet even with boats going by. Would definitely stay here again!

Danielle was a wonderful host, and her place was absolutely beautiful. Great location, and the biggest plus was that they offered convenient items on property for use at the beach, kayaking in the bay, and just clean fun while taking an easy day around the house. We had everything we needed plus more while there. I would certainly consider staying there my next trip to the keys. Marathon Key was my favorite, anyway. 10/10 recommend this property.

We were there to celebrate my husband's 50th birthday. The master bed, pillows and linens were very comfortable. The screened in porch with plenty of comfortable seating was our favorite amenity of the property. We hope to rent there again when we are back in the area. Very comfortable and very clean. 😁

we totally enjoyed our stay. the home is spacious and has everything you would want or need for your stay. loved the screened in porch area! thank you!!!

The house was very clean and inviting upon arrival. Nice location short drive to great restaurants and local grocery stores also less than 5min walk to the beach. Mr Eddie responded in a timely manner when we had questions. All in all we had a great time and very much enjoyed our stay! Thanks Mr Eddie

It’s awesome. The additional fees are worth it. The community is great and the commitment to keeping the neighborhood classy is excellent.

Adorable little 2 bdrm home on a bay. Very cute, clean. Kids can fish at back of the house. Plenty of activities to do on the property. Feels like a 55 and up community, lots of older women walking in the pool that didn’t like kids playing. “Resort” fee $125 NOT included which is very overpriced, but does pay for security and the grounds are very safe. Supplies for laundry and kitchen well stocked.

Loved every minute of our time here. Communication was excellent before during and after our stay and the house was superb. Highly recommended

This was a great place for our family. We had plenty of space to relax. The home is well stocked with linens, kitchen items and paper goods. We only had to buy groceries. The tvs had streaming services and there are two types of coffee makers!

We had a wonderful time staying at Tim’s place! He was an excellent host who was always available if I had a question. The house is in a beautiful location. We enjoyed sitting on and fishing off the dock. The house had everything we needed for a fantastic stay and a very enjoyable vacation. I can’t say enough good things about our experience at the home. We were able to meet Tim and he was a lovely host. Thank you for a great vacation! We hope to come back in the future!

The place was perfect. The patio views were amazing to just sit and watch the sunset. The marina across the street was very convenient to launch our boat from. Very peaceful location. Angler and ale restaurant across the street was delicious

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.

We are absolutely in love with this place. The views are gorgeous. the grounds were immaculately groomed. There are so many colorful trees and flowers. The pool is slightly heated, which is perfect. Everyone we met was so nice and helpful with recommendations. We got to see the jets fly over a few times, so cool. The kitchen has everything you need to prepare meals and snacks. The beds in both rooms are very comfortable. We hope to stay here again in the future.

Exceptional stay. Anchor Drop was a top Airbnb property in our book.,Would definitely look to return to both Key West and the property. Host was responsive, explicit, and helpful. Space was as described and very well appointed, clean, and comfortable. First time to Key West and was very satisfied with our accommodations, location, and area. Thank you!

Absolutely perfect for a honeymoon getaway, quiet perfect amount of space for us, the set up was great with 2 bathrooms and a huge walkin closet, the couches were super comfy, the TV was big enough to see from across the room, we enjoyed everything about it. Got to meet some of the neighbors and they were all very welcoming and enjoyed talking to them. Scott had some great local recommendations and we enjoyed everything.

The condo was exactly as pictured, clean, quiet and close enough you could walk to some things, I would suggest taking an uber to downtown especially during the summer. The restaurant/bar Mac’s next door has good food. The noise others complain about we could not really hear inside the condo, so not sure why that was mentioned by others. We had a great time, ate some great food and explored a lot of what Key West has to offer. We would definitely stay in this condo again. Thanks Jennifer for sharing your beautiful place with us.

The location couldn't be better. Large deck with view of the ocean in distance, very nice large pool just steps away, very quiet (except occasional airplanes - well, it's a small island after all) and the 5:00 pm fog horn last-boarding-warning from the cruise ship in port... kind of appropriate since the building's architecture looks a bit like a cruise ship - added to the vibe. Oh the SUNSET VIEW!! Within walking distance to the best part of Duval, the best restaurants and less than 15 minute bike ride to the best (Ft Zachary) beach. We Will be back if we can!!

Our first time visiting the Keys and Celia’s place made it wonderful! Located in a very nice, quiet, and safe community her condo is like new and so well cared for. Perfect size for our two couples. The decor and furniture is very nice, bright and clean. Had all the amenities we needed and then some. We enjoyed the heated pool everyday and the private beach was nice for a more natural experience. The furnished patio had a great view of the pool and ocean. Celia is a wonderful host! Very helpful and a great communicator.