Cudjoe Key vacation rentals
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Top-rated vacation rentals in Cudjoe Key
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Cudjoe Key vacation rentals
Cudjoe Key house rentals
Home in Key West
4.95 out of 5 average rating, 278 reviewsRomantic Retreat - 2 person K Suite, Pvt deck/Spa!
Home in Marathon
4.91 out of 5 average rating, 160 reviewsBeachfront Villa - Florida Keys
Home in Marathon
4.9 out of 5 average rating, 138 reviewsWaterfront Cozy Modern Retreat w/Deep Canal
Home in Cudjoe Key
4.88 out of 5 average rating, 77 reviewsIsland Oasis ~ YOUR Paradise Awaits!
Home in Cudjoe Key
5.0 out of 5 average rating, 9 reviewsVenture Out- Million Dollar Island Resort
Home in Cudjoe Key
4.88 out of 5 average rating, 50 reviews*Emerald Seas*-Florida Keys Ocean Front Paradise!
Home in Cudjoe Key
5.0 out of 5 average rating, 13 reviewsSea Turtle Cove
Home in Cudjoe Key
5.0 out of 5 average rating, 3 reviewsLatitudes-Ocean Front Pool
Other great vacation rentals in Cudjoe Key
Tiny home in Big Pine Key
4.8 out of 5 average rating, 99 reviewsBreezy pines 28 foot 5th wheel trailer .
Cottage in Cudjoe Key
4.92 out of 5 average rating, 85 reviewsKing Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
Vacation home in Cudjoe Key
5.0 out of 5 average rating, 40 reviewsBeautiful Cottage & Amenities in Gated Community
Place to stay in Cudjoe Key
5.0 out of 5 average rating, 8 reviewsKeysie Does It @ Cudjoe Key - Home in Waterfront
Home in Cudjoe Key
4.88 out of 5 average rating, 84 reviewsHappy Hibiscus Home
Home in Cudjoe Key
4.94 out of 5 average rating, 18 reviewsMay Extravaganza - Relax in Paradise!
Camper/RV in Big Pine Key
4.93 out of 5 average rating, 45 reviewsHaving fun in the lower Keys
Guest suite in Key Colony Beach
4.99 out of 5 average rating, 86 reviewsTurtle-By-The-Sea: the Best Deal in KCB!
Quick stats about vacation rentals in Cudjoe Key
Total rentals
190 properties
Rentals with a pool
140 properties have a pool
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
160 properties are a good fit for families
Total number of reviews
4K reviews
Nightly prices starting at
$110 before taxes and fees
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 60 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 80 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 $130 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 100 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 150 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 60 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 140 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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