Cudjoe Key vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Cudjoe Key vacation rentals

Stay near Cudjoe Key's top sights

Square Grouper Bar and Grill47 locals recommend
Sugarloaf Key / Key West KOA Holiday3 locals recommend
My New Joint27 locals recommend
Mangrove Mama's21 locals recommend
Cudjoe Sales Fishermen's Warehouse4 locals recommend
Sugarloaf Food Co3 locals recommend

House rentals in Cudjoe Key

Superhost
Home in Marathon
4.8 out of 5 average rating, 15 reviews

Home in Marathon w/ boat lift

KristenRating, 5 stars3 weeks ago
Stay was great. The house worked well for our family of four with 2 teenagers. Bunk beds comfortable, primary bed was pretty firm though. We appreciated the kayaks, access to water, location was great. Back yard was a great place to hang out. Check in was very easy with keypad. Easy to find. Overall we enjoyed it! Thank you!
Superhost
Home in Key West
4.71 out of 5 average rating, 7 reviews

Serene Lily~ Luxurious 2 bed, 2.5 bath home

RoyRating, 5 stars1 month ago
Beautiful home and we enjoyed our stay. We felt right at home and the pool was a nice walk. The kitchen had anything you would need to make a meal. We will definitely come back again. Thank you.
Superhost
Home in Key Colony Beach
4.96 out of 5 average rating, 26 reviews

Fins to the Left 2 bed 2 bath Duplex w/ Cabana Clu

TiffanyRating, 5 stars3 months ago
This unit in Marathon had everything for relaxing and quiet vacation. The furniture and artwork were very well selected and made the stay more upscale. Super clean and excellent quality bed linens and kitchen gear. Concierge arranged for bike rentals so we could easily explore the area. We biked, walked and drive from Key West to Islamorada daily. Our fav vacay rental thus far!
Guest favorite
Home in Key Colony Beach
4.95 out of 5 average rating, 111 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

JessRating, 5 stars4 days ago
We loved our stay! The house was super clean and the back patio was beautiful. We loved the back canal area and saw lots of very cool wildlife and enjoyed fishing right there. Having the kayaks to use was also great. Beds were very comfy and the rooms were spacious. The house had everything we needed. We loved the key colony area. The cabana club was a great space and the house is in walking distance to Sunset Beach, which was beautiful. The whole area is super close to fun things to do and great restaurants. We would absolutely stay here again!
Guest favorite
Home in Key Colony Beach
4.95 out of 5 average rating, 42 reviews

Casa Lago Mar 3/2 with Cabana Club Access

TimRating, 5 stars3 months ago
We loved staying at Melissa’s Airbnb. The neighborhood was nice and very walkable. Loved being right on the canal. The Cabana Club was great for kids with the pool and beachfront area. Marathon was a great Key to stay on with lots to do. The duplex was clean and beds were comfortable. Loved sitting out on the back porch in the morning with coffee. We would definitely recommend and would love to come back someday.
Superhost
Home in Key Colony Beach
4.8 out of 5 average rating, 25 reviews

Cozi home with dock

WoodrowRating, 5 stars6 months ago
Look no further for the place to stay with kids and or dogs! Cabana club is super nice!! They should update the pics of the place because it’s way nicer than the pics!! Instacart and door dash works well!! Really can’t say enough good!
Guest favorite
Home in Key Colony Beach
4.91 out of 5 average rating, 134 reviews

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

MelissaRating, 5 stars4 weeks ago
Had a wonderful, peaceful stay. We fished off the dock area, enjoyed time at the cabana, walked every morning enjoying the views and participated in the sunset community almost every night at the park! Great vacation for our multigenerational needs!
Superhost
Home in Summerland Key
4.88 out of 5 average rating, 34 reviews

Pelico Palms Sunset Suites

TimRating, 5 stars5 days ago
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!

Other great vacation rentals in Cudjoe Key

Guest favorite
Home in Marathon
4.96 out of 5 average rating, 24 reviews

Home near beach & restaurants

PamelaRating, 5 stars1 week ago
We had a great time at “Home near beach and restaurants” in Marathon. I would say the high points of this place were: - It was very clean - It was very comfortable in terms of the shared living space as well as the two bedrooms and baths. - We ate in 5 out of 7 nights (but one of those was pizza) and the kitchen was very well stocked. - I loved having a working icemaker in the refrigerator - And the air conditioning worked wonderfully (it was very warm outside). - We enjoyed going to the beach multiple times and there was beach “stuff” included that we definitely made use of.
Guest favorite
Guesthouse in Marathon
4.95 out of 5 average rating, 21 reviews

The Pink Dolphin House.

PatrickRating, 5 stars2 weeks ago
Beautiful ocean views and great local recommendations from the host! Some aspects of the interior were a bit dated, but with multiple areas to enjoy the outdoors (offering full shade to full sun and everything in between), we didn't do much inside except sleep. Kids spent hours per day in the pool and adults most enjoyed lounging on the jetty with 345 degrees of ocean views. Board games (and a ps3) were available for the occasional down time. The location allows for a feeling of privacy on the ocean while offering many hidden gems for dining and activities nearby.
Top guest favorite
Home in Cudjoe Key
5 out of 5 average rating, 16 reviews

Oceanside home 111, dock,kayaks,bikes,pool,fishing

JenRating, 5 stars1 month ago
Great house- clean, well equipped kitchen, comfy beds. Beautiful views-early risers get a great view of the moon from bedroom deck. Sunsets- yes! John provides kayaks- easy and fun to see turtles pop up and fish swim by. Bikes are provided but nowhere to really ride- roads aren’t bike friendly unless you take them somewhere. Nice dock to hang out on- fishing from dock- ehh- not great but kemp bridge 2 miles away is pretty good- snappers, grunts. Enjoyed the pelicans, geckos, and even watched an iguana stroll by. Bahia Honda state park- 20 min drive- beautiful park with beaches, trails, marina. Overall wonderful, relaxing week!
Guest favorite
Villa in Marathon
4.95 out of 5 average rating, 135 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

GregRating, 5 stars4 days ago
This was the perfect space for our family of seven. Cleanliness and all the creature comforts were fully up to our expectations. The interactions we had with Dennis were quick, attentive and friendly. Highly recommend!
Guest favorite
Home in Cudjoe Key
4.93 out of 5 average rating, 45 reviews

Private Ocean Oasis by Key West, Florida

JeremyRating, 5 starstoday
Awesome place , well described in a perfect location . The amenities in the resort were awesome, lots to do. Ronda was very responsive with my questions I had about the area and things to do thru out. Will definitely be rebooking with her in the near future. Thanks again Ronda!
Top guest favorite
Home in Marathon
4.91 out of 5 average rating, 176 reviews

Beachfront Villa - Florida Keys

ErinRating, 5 stars1 week ago
This is a fantastic property! Right across from Sombrero Beach but still peaceful and private. The house and yard is like an oasis. Host and management company are WONDERFUL! Highly recommend!
Superhost
Home in Marathon
4.6 out of 5 average rating, 5 reviews

Coastal Paradise: 5-Bed Retreat

TrishRating, 5 stars2 weeks ago
We loved our latest stay in Marathon. We traveled with two families (2 teens, 2 older children). The house layout was perfect for our group. It was nice to have the kitchenette downstairs by the patio slider for pool snacks (small microwave) and clean-up from beach days/pool days. The beds were all newer, stylist beach decor, & ample space. There is lots of indoor and outdoor (covered and uncovered) table/conversation seating. The pool and hot tub were great. We spent many nights in the hot tub looking at the stars and relaxing. Although, you on a canal with other houses, it’s very quiet. The canal had fish, sharks, and even a cute manatee that visited in the morning. Our kids loved fishing daily. As for location, it’s perfect. You’re only a few miles from Sombero Beach, Sunset Beach, and 7 mile bridge. Publix, bait shops, restaurants all within a short drive. You cannot walk to beaches, but we didn’t mind this. There is a bike trail on Aviation Rd. Near the house.
Superhost
Home in Marathon
4.75 out of 5 average rating, 4 reviews

SeaEsta! Bring your boat & 1 block to the beach!

KellyRating, 5 stars1 month ago
Our stay at John's place was amazing. The location was perfect as we went up and down the Keys spending time in Islamorada and a day in Key West. We walked the neighborhood and to Sombrero Beach. The set up for our boat was fabulous. We were able to leave it in the water to use everyday. The best part of John's house was the outdoor area in back. We stayed out there more than anywhere, of course the weather was perfect. Thank you for sharing your place with us John. We hope to be back!

Quick stats about vacation rentals in Cudjoe Key

  • Total rentals

    270 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 before taxes and fees

  • Total number of reviews

    5.1K reviews

  • Family-friendly rentals

    210 properties are a good fit for families

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    210 properties have a pool

Your guide to Cudjoe Key

Welcome to Cudjoe Key

Flutter your eyelids as you travel down the Overseas Highway and you might just miss Cudjoe, an under-the-radar island perched between the more recognizable Sugarloaf and Big Pine Keys. At less than 6 square miles and with fewer than 2,000 residents, this island is shaped like an elephant’s head and serves mostly as a tranquil beach escape, with easy access to neighboring attractions. There’s Blue Hole, the region’s largest freshwater lake, which provides opportunities for spotting turtles, alligators, and exotic birds. There’s also diving and snorkeling at the nearby Looe Key National Marine Preserve, but the real fun here happens during the yearly Florida Keys Underwater Music Festival. Key West and its plentiful attractions are just a coconut’s toss — okay, 20 miles — to the southwest.


The best time to stay in a vacation rental in Cudjoe Key

It’s pretty much always warm on Cudjoe Key, and between November and March it’s also sunny, which tends to attract a large number of visitors. Despite the risk of summer rain, June through October are also great months to visit for snorkeling and diving, though do keep in mind that hurricanes become increasingly likely in late summer and into early fall. Come in January or February and you’ll definitely want a light jacket for the evenings. The Underwater Music Festival, during which costumed divers pretend to play subaquatic instruments, usually takes place in July.


Top things to do in Cudjoe Key

Key West

The eccentric crown jewel of Florida’s archipelago is worth a visit for its classic Caribbean-inspired homes and lively nightlife scene. Visit old stamping grounds popularized by famous writers and cruise over to Fort Zachary Taylor Historic State Park, where you can swim with some big fish.

Looe Key National Marine Preserve

More than 150 fish species, along with plenty of sharks and rays, are known to shimmy through these waters and along the abundant coral reef, making this preserve a solid snorkeling and diving spot. There’s also an artificial reef about three miles west, where a 210-foot sunken ship offers superb wreck diving.

Blue Hole

This former limestone quarry is now a freshwater lake replenished by rainfall and visited by a large variety of wild animals, including Key deer, alligators, turtles, and numerous species of birds. The lake is part of the National Key Deer Refuge, and worth a visit for a chance to spot the majestic and miniature endangered creatures.

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Cudjoe Key?

    Yes! Work meets play with ease at over 70 vacation rentals in Cudjoe Key featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Cudjoe Key?

    Four-legged friends are welcome in Cudjoe Key. Choose from more than 120 vacation rentals for guests traveling with pets.

  • How much does it cost to stay in house rentals in Cudjoe Key?

    Experience the best of Cudjoe Key with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there Cudjoe Key house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 150 house rentals with pools in Cudjoe Key, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Cudjoe Key have wifi?

    Absolutely! We offer over 200 house rentals with wifi in Cudjoe Key. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cudjoe Key have a bbq area?

    Absolutely! We offer over 50 house rentals with a bbq area in Cudjoe Key. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cudjoe Key have self check-in?

    Absolutely! We offer over 30 house rentals with self check-in in Cudjoe Key. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Cudjoe Key?

    Cudjoe Key has more than 190 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

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