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House holiday rentals in Cudjoe Key

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Popular amenities for house rentals in Cudjoe Key

House rentals with a pool

Guest favourite
Home in Cudjoe Key
4.92 out of 5 average rating, 24 reviews

Pelican's Roost, Waterfront comfort at Venture Out

PamRating, 5 stars2 months ago
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!!!
Guest favourite
Home in Cudjoe Key
5 out of 5 average rating, 6 reviews

Moana Hale Paradise #164 - Venture Out, Cudjoe Key

anthonyRating, 5 stars2 months ago
It’s awesome. The additional fees are worth it. The community is great and the commitment to keeping the neighborhood classy is excellent.
Superhost
Home in Key Largo
5 out of 5 average rating, 4 reviews

Newely Renovated 3/2-private pool/dock/cabana club

OliviaRating, 5 stars1 week ago
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!
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 60 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

DanielRating, 5 stars2 weeks ago
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!!!
Superhost
Home in Cudjoe Key
4.89 out of 5 average rating, 19 reviews

Mermaid Magic at Venture Out

MistyRating, 5 stars3 months ago
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.
Guest favourite
Home in Marathon
4.92 out of 5 average rating, 12 reviews

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront

HansRating, 5 stars2 weeks ago
Loved every minute of our time here. Communication was excellent before during and after our stay and the house was superb. Highly recommended
Superhost
Home in Summerland Key
4.89 out of 5 average rating, 36 reviews

Pelico Palms Sunset Suites

AubreyRating, 5 stars1 month ago
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!
Superhost
Home in Summerland Key
5 out of 5 average rating, 3 reviews

Waterfront Beach House with Dock & Heated Pool!

HeatherRating, 5 stars1 month ago
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

Top guest favourite
Home in Marathon
5 out of 5 average rating, 38 reviews

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

JillRating, 5 stars1 month ago
If I could rate this stay a 20, I would. We came across the listing last June, after wanting to try something different on our annual trip to Marathon. It looked perfect for our family. What I didn’t expect when we arrived on April 16, 2025, was to be blown away. The pictures don’t do it justice. The house is STUNNING. I felt like we were walking in/staying at a brand new house as the very first guests. The colors, the furnishings, the level of coziness brought to this luxury beach house was unmatched. The towels (bath and beach) were plush and soft. Pool speakers. The bar! I mean everything. The kitchen was stocked with what you need - high end gadgets, utensils that actually work, and every pot and pan (organized). Immaculately cleaned. And then the views. Holy guacamole. My dad parked himself on the main floor deck and didn’t move for seven days. Airbnb was right- RARE FIND. Amanda - you are the hostiest host in the world. Your communication was 💯. And we pray to make it back to yo
Top guest favourite
Home in Marathon
5 out of 5 average rating, 17 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars1 week ago
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!!
Guest favourite
Home in Marathon
4.94 out of 5 average rating, 35 reviews

Florida Keys Oceanside Utopia

CaroleRating, 5 stars1 month ago
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!
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 26 reviews

Million Dollar View

JohnRating, 5 stars1 month ago
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.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 40 reviews

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

AnneRating, 5 stars1 week ago
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.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 51 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

RickRating, 5 stars1 week ago
We had an amazing family weekend here! The home was spotlessly clean, beautifully maintained, and incredibly well equipped with everything we needed. The ping pong table, video games, and sail kayaks were huge hits with the whole family. We also rented a boat, and having a private dock made that experience seamless and unforgettable. The location was quiet, safe, and perfect for quality time—cozy enough to relax, yet close to everything we needed. It truly felt like a home away from home. For all the amenities and the exceptional condition of the property, the price was a fantastic value. We’ve stayed in many vacation rentals, but this one stands out as one of the best. We’re already looking forward to coming back. Highly recommended!
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 34 reviews

Viamarhe House-Private beach, Kayak, yard games

AmandaRating, 5 stars1 week ago
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.
Superhost
Home in Marathon
4.89 out of 5 average rating, 64 reviews

Gorgeous Ocean View Home!

ChristinaRating, 5 stars1 month ago
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.

Private house rentals

Guest favourite
Home in Marathon
4.96 out of 5 average rating, 23 reviews

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

HaleeRating, 5 stars6 days ago
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! :)
Home in Cudjoe Key
4.71 out of 5 average rating, 7 reviews

Paradise Point Getaway in Cudjoe Key

AliciaRating, 5 stars1 month ago
We had a great time and relaxing stay, only one issue which was out of everyones hands the but I highly recommend staying here it is a great location and lots to do.
Guest favourite
Home in Key Colony Beach
4.99 out of 5 average rating, 107 reviews

ABeachBungalow-60’dock w/ access to pool and beach

DesireeRating, 5 stars1 month ago
We enjoyed our stay and felt very at home. I had a few questions when settling in and I got responses very quickly. The house was tidy, the location was perfect and the kayaks were fun (be careful getting in the water as the rocks are very slippery). The owners recommended babyquip which was very helpful in providing toys, a crib and a high chair for my little ones.
Superhost
Home in Summerland Key
4.58 out of 5 average rating, 84 reviews

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

SarahiRating, 5 stars1 month ago
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.
Guest favourite
Home in Marathon
4.97 out of 5 average rating, 68 reviews

Sombrero beach oasis, great location, many amenities

KendallRating, 5 stars3 weeks ago
Incredible for a family vacation. 🏝️The property feels very private, clean, well decorated, and many amenities. We tried out the paddle boards and spent a lot of time in the pool. When going to the beach, Aileen already had chairs and towels to bring! This property really is a gem. Thank you Aileen!
Guest favourite
Home in Marathon
4.94 out of 5 average rating, 90 reviews

Conch Cottage at Hawks Cay - Chic Tropical Retreat

VicenteRating, 5 stars4 weeks ago
Loved it! I hope to go again some day in the near future.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 11 reviews

Endless Summer

LisaRating, 5 stars2 weeks ago
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.
Guest favourite
Home in Marathon
4.9 out of 5 average rating, 20 reviews

Ocean Escape 97

LisaRating, 5 stars1 month ago
Omg what can’t I say about the house. Beautiful! Very friendly neighborhood. Extremely clean and beautifully maintained. The host were available and responded so quickly. We loved it and will be back! Thank you so much for sharing paradise with us!

Quick stats about house rentals in Cudjoe Key

  • Total rentals

    200 properties

  • Nightly prices starting at

    ₹3,443 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Cudjoe Key
  6. House rentals