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

Keysie Does It at Cudjoe Key
We absolutely loved our stay! Our checkin was smooth and flexible. The home was squeaky clean, linens and beds were unbelievably soft and comfortable, and there were more supplies/ amenities in the home than listed. We felt right at home and would love to come back! Absolutely 5 star place!

Cancellation Deal: 08/02 thru 08/09
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

Newely Renovated 3/2-private pool/dock/cabana club
Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!

Beach House, Private Pool & Dock, Gulf Sunset view
Our 7 day stay was the most relaxing vacation we’ve had in years. The location was somewhat remote but only a short drive into Marathon. We hope to come back soon!!!

Lower Keys Paradise
We needed to be near summerland key for work all week, but no short-term airbnbs on thT key. This was key adjacent, the rental was comfortable, the pool and hot tub were great for unwinding at the end of each work day.

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront
Loved every minute of our time here. Communication was excellent before during and after our stay and the house was superb. Highly recommended

Pelico Palms Sunset Suites
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!

Waterfront Beach House with Dock & Heated Pool!
House was very clean, host very responsive, beautiful location, pool was perfect and the view was amazing. Definitely recommend and will be staying there again.
Weekly house rentals

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys
Thank you so much for such an amazing stay! We loved the gorgeous property and all the lovely decor inside! Property was extremely clean and Sandy was so kind and helpful! We spent almost every evening in the hot tub! The home had everything we neded for an awesome week and was in a great central location, close to everything we wanted to do! We loved TJs Tiki Bar for dinner and a beautiful sunset! Thank you again Sandy! :)

Florida Keys Oceanside Utopia
Shane and Kelly were fabulous! My husband and I enjoyed a week away and loved exploring Marathon. Fishing from the back deck was so much fun. We caught some mangrove snapper that we made for dinner which was exquisite! I also caught a Jack Cravalle and my hubby caught a shark. Definitely fun times! Explored beaches, hiked and went to Key West for a day. Weather did not disappoint. Highly recommend this great vacation home!

Dock Pool Ramp Jacuzzi Ocean Views Kayaks
This stay was the perfect vacation I was looking forward to, I stayed 7 days at this water front property with a great balcony to enjoy evenings and a boat ramp to launch the boats in the back yard along with the pool to keep us cool. Plenty of room for our trucks and trailers, the inside of the home was comfortable and relaxing. Was truly a great vacation Thank you

Million Dollar View
This home was everything we expected and more. Stunning location with absolute privacy. The extra long dock was amazing, the pool was fantastic, and the grounds were meticulous. It’s literally your own private resort. Roman, the host, was very quick with communication. He and his wife actually met us when we checked in to see if we had any questions and provided us with an arrival gift. If you have looked at the listing and are thinking of renting it, do it. You will not be disappointed at all. Excellent value all around.

Movie Theater | HotTub | Pool | Boat/RV/EV Parking
We almost stayed at a hotel, but I saw Christian’s place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. It’s also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.

Viamarhe House-Private beach, Kayak, yard games
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.

Gorgeous Ocean View Home!
We had an amazing time with our family and a beautiful Easter dinner with our friends. The location is perfect to travel all of the keys as it's just over an hour to Key West and Key Largo. The sun rose over the top floor guest bedroom with such a beautiful view of the water every day. Morning coffee with the view was awesome. Evenings spent wrapped on the couch watching movies with really nice big TV and unwinding. Sitting down by the water in evenings before sunset hanging with family watching niece play in sand was great too. Highly recommend.

Keysgetaway Retreat. Fish#Fun#Relax
It was a great place. She was on top of things. Water went out not just at her place the whole keys because of main break. She was on top of it went we let her know of the problem and she found out the problem and got back to us.
Private house rentals

Waterfront with Boat Lift/Kayaks and Hot Tub
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!

Coral Lagoon #23- Private Villa Home
Wonderful Stay! Place was super clean and nicely decorated with minimal decor. (Sometimes places are over decorated and busy) Beach Towels were provided. Kitchen was organized & clean. Pool was nice! We brought our small dogs and the grounds were very pet friendly. Jessica’s recommended list of restaurants was spot on! Had a great time eating at several of the places. Would visit again and recommend to others.

Waterfront Escape -VACA-23-408
we were a family of 6 staying and had more then enough room. the house was perfect and had everything you needed. we enjoyed fishing off the deck and watching the manatees everyday day swimming by. the backyard was absolutely perfect to hang out and relax. Carmen is a great host and communicates fast. would absolutely stay here again.

Discount Available! 100' Dock, Lots of Amenities!
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS
We had a great long weekend at Alex house! You are provided with a starter kit, so you may need to buy extra supplies if planning to stay in at property. House vibes are very keywest. Winn Dixie very close and Bahia Honda state park was close by and beautiful to spend the day if looking for something to do. Keywest about 40 min drive, easy to get around. Had plenty of blankets, pillows and accommodated 10 of us— we did bring an air mattress which I would recommend as sofa beds are not the most comfortable. Has a beautiful backyard which we spent a lot of time on and yummy walkable restaurant. Plenty of parking. Host was very responsive and checked in with us to make sure check in was smooth.

Grouper Getaway @ Ocean Isles Fishing Village
Great property, exactly like the photos and descriptions. Ben was extremely proactive and responsive. I would highly recommend this property.

P36 - Charming and immaculate 2 Bedroom, 2 bathroo
Great place! Very spacious, nice dock and out door and area to enjoy with the pool! It was nice having a large deep freezer for ice and fish!

Spacious lux home, private pool/spa, 80' dock
The house was exactly how it was described online. Everything was well marked. Lots of stuff to do at the home. Very spacious and well maintained. There were only 7 of us, so lots of extra space. The pool is on the perfect side so your not blasted with the late afternoon sun. However, there is a huge umbrella in case it is needed. Kitchen is fully stocked so nothing was needed. There is a BBQ grill as well as a flat top which is nice for outside cooking. The only thing I would recommend is to bring your own pillow if your a particular pillow person (we love our feather pillows), house pillows were not feather ones. If you rent here and have a boat definitely go to the Sombrero Lighthouse to snorkel. Never saw so many fish in one place. The Conch Cafe and Coast to Coast pizza are both great food restaurants and walkable from the home. Publix is so close it was a daily visit. Truly enjoyed the week stay!!!!!
Quick stats about house rentals in Cudjoe Key
Total rentals
200 properties
Nightly prices starting at
$51 SGD before taxes and fees
Total number of reviews
3.8K reviews
Family-friendly rentals
190 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
150 properties have a pool
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