Cudjoe Key vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.
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

Cudjoe Key house rentals

Superhost

Home in Key West

4.6 out of 5 average rating, 5 reviews

Serene Lily~ Luxurious 2 bed, 2.5 bath home

EdRating, 5 stars10 months ago
Excellent experience. The property was immaculate and the host 5 star. We would definitely rent from this host again.
Guest favorite

Home in Marathon

5 out of 5 average rating, 32 reviews

Viva La Playa.Single family 3/2. Ocean view. New

Jacqueline Rating, 5 stars3 weeks ago
Great place to stay. Gorgeous house! Host was very helpful. Spotlessly clean. Perfect location for us. Very short drive to supermarkets & beach. Would definitely recommend. It was very quiet considering the busy road and airport.
Guest favorite

Home in Key Colony Beach

4.87 out of 5 average rating, 23 reviews

Cozi home with dock

WoodrowRating, 5 stars4 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

4.92 out of 5 average rating, 132 reviews

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

AnneRating, 5 stars2 weeks ago
Looks just like the photo’s. Unfortunately weather was a little chilly the first couple of days. When it warmed up we enjoyed the local cabana club with the heated pool, beach and restaurants. The accommodations were spacious and clean.
Superhost

Home in Summerland Key

4.93 out of 5 average rating, 27 reviews

Pelico Palms Sunset Cottage

CassRating, 5 stars3 months ago
Wonderful place to stay, starry night skies, key deer, iguanas, beautfil pool. Very clean. Nate was absolutely terrific start to finish, super responsive and helpful beyond the call of duty.
Guest favorite

Home in Key Colony Beach

5 out of 5 average rating, 80 reviews

“La casa azul” step 3’ to a private pool

AnthonyRating, 5 stars3 weeks ago
We really enjoyed our stay at La Casa Azul. Key Colony beach is quiet and has lots to do. Being on the channel was fun, sitting in the pool and watching neighbors fish or the boats strolling by. The house was perfect and spacious for two and would be equally roomy for 4 (but we left the kids at home!) The host was extremely responsive and helpful throughout our stay and made us feel right at home. Thanks Janine!
Guest favorite

Home in Key Colony Beach

4.9 out of 5 average rating, 21 reviews

P67 - New Construction 3 bedroom 4 bath with priva

TammyRating, 5 stars5 months ago
This place is beautiful! It was extremely clean when we arrived. The kitchen was well stocked with the essentials we needed. (However we didn't cook much, loved having an air fryer and blender). The beds were lovely! We loved the pool and the outdoor seating areas! Perfect size pool to cool off. We rented a boat and the dock was perfect. We brought our paddle boards and the canals were great for safe and relaxing paddle boarding. Close drive to restaurants and shopping. The neighborhood was safe and beautiful.
Superhost

Home in Summerland Key

5 out of 5 average rating, 3 reviews

Family Retreat

AngelaRating, 5 stars2 weeks ago
Beautiful view and clean home. Watch gorgeous sunrises right from the screened in porch or out on the dock. Great local restaurants close. We highly recommend The No Name Pub (amazing pizza, and make sure you bring a dollar for their wall). The Bent Prop was another favorite and was only about half a mile away. Breakfast recommendation is to go to Key West to Blue Heaven (try the banana bread)!

Other great vacation rentals in Cudjoe Key

Superhost

Home in Key Colony Beach

5 out of 5 average rating, 4 reviews

Huge Swim Spa~ Incredible Special Fall Pricing

JillRating, 5 stars1 month ago
The house was exactly as described. We used all the things provided. The swim spa was great. Everything was provided to fish. The bikes were so fun to use to get around the area. The paddle board and kayaks were fun for the kids. Sherry was very good at communicating with us. We would definitely go back here!
Guest favorite

Home in Marathon

4.95 out of 5 average rating, 20 reviews

Home near beach & restaurants

HowardRating, 5 stars3 weeks ago
Review by male in late-seventies : Coastal Charm was bright, modern, spacious, nicely decorated, excellent beds, accurate photos, without a dishwasher or food disposal, superb a/c and internet, nice TVs in 3 areas, a Mr. Coffee but no Keurig. The front door faces 114th St. We parked in front on 114th .The mailbox is on the side facing 3rd. We liked and enjoyed the place for a week in the middle of January.
Guest favorite

Guesthouse in Marathon

4.94 out of 5 average rating, 18 reviews

The Pink Dolphin House.

ScottRating, 5 stars3 weeks ago
We absolutely loved Margaret's place! It was picturesque and so fun! We loved the view, the pool, the local restaurants and her home felt very comfortable for my family of five. Thank you Margaret and Phil!!!
Guest favorite

Home in Cudjoe Key

5 out of 5 average rating, 27 reviews

Paradise in Cudjoe! Perfect Family Home!

JordanRating, 5 stars3 months ago
Taylor and Kali were friendly and polite. Very accommodating and the location was perfect. Loved having the space to filet fish and easy access to open water. Would def recommend!
Guest favorite

Villa in Marathon

4.95 out of 5 average rating, 130 reviews

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

DawnRating, 5 stars1 week ago
The space was perfect for our family get away. Enjoyed the kayaks, paddle boards, pool and out door seating. Kitchen well appointed. Each couple had own bath which was nice as well. Nice walk to the beach.
Guest favorite

Home in Cudjoe Key

4.93 out of 5 average rating, 45 reviews

Private Ocean Oasis by Key West, Florida

DonnaRating, 5 stars1 month ago
This was the perfect place to meet up for a Christmas gathering with our adult children. The home was so nicely decorated and furnished and had EVERYTHING we could have needed for a three day stay. There was plenty to do on the Venture Out Resort property and anything else you’d want or need is within driving distance. Will definitely stay here again!
Guest favorite

Home in Marathon

4.91 out of 5 average rating, 170 reviews

Beachfront Villa - Florida Keys

ZaneRating, 5 stars1 week ago
I highly recommend this house to anyone looking for a place to stay in Marathon. Its location could not be more perfect - right across the street from Sombrero Beach and the children’s park. We traveled with our 3 year old and 1 year old and this place was so kid-friendly! Being so close to the beach was perfect for us so the kids could eat decent meals and get naps all without taking us away from our beautiful beach days! Loretta was also very friendly and proactive in making sure we had everything we needed for our trip! We cannot wait to book our return trip!
Superhost

Townhouse in Marathon

4.95 out of 5 average rating, 21 reviews

Waterfront luxury Villa (29) with sunset views and boat slip

CarissaRating, 5 stars43 months ago
Couldn’t have imagined a better stay, view, location, convenience for our boat up staycation. It was perfection! Bonus, balcony overlooking the canal doubled as my yoga studio!!

Quick stats about vacation rentals in Cudjoe Key

  • Total rentals

    270 properties

  • Nightly prices starting at

    $80 before taxes and fees

  • Total number of reviews

    4.6K reviews

  • Family-friendly rentals

    210 properties are a good fit for families

  • Pet-friendly rentals

    130 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 130 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 $120 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 140 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