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
Get the amount of space that is right for you
Popular amenities for Cudjoe Key vacation rentals
Cudjoe Key house rentals
Home in Cudjoe Key
4.89 out of 5 average rating, 18 reviewsPelican's Roost, Waterfront comfort at Venture Out
Home in Marathon
5 out of 5 average rating, 36 reviews100' Dockage, Pool, Kayaks, Paddle Board, Bikes!
Home in Cudjoe Key
4.83 out of 5 average rating, 41 reviewsRelaxing Home in the Keys
Home in Marathon
5 out of 5 average rating, 22 reviewsMermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!
Home in Cudjoe Key
5 out of 5 average rating, 14 reviewsVenture Out- Million Dollar Island Resort
Home in Cudjoe Key
4.85 out of 5 average rating, 26 reviewsLower Keys Paradise
Home in Cudjoe Key
4.89 out of 5 average rating, 83 reviewsIsland Oasis ~ YOUR Paradise Awaits!
Home in Cudjoe Key
4.93 out of 5 average rating, 15 reviewsBetty's Place
Cudjoe Key cottage rentals
Cottage in Islamorada
4.97 out of 5 average rating, 59 reviewsIslamorada bungalow 2 bed & pool
Cottage in Marathon
4.96 out of 5 average rating, 24 reviewsCatch n' Relax Canalfront Cottage in Marathon
Cottage in Marathon
4.96 out of 5 average rating, 26 reviewsWATER FRONT COTTAGE W/ MOTHER IN LAW TREETOP SUITE
Cottage in Cudjoe Key
4.86 out of 5 average rating, 35 reviewsTidewater Views at Venture Out
Cottage in Key West
4.87 out of 5 average rating, 39 reviewsNamaste: A blissful one bedroom cottage
Cottage in Cudjoe Key
4.64 out of 5 average rating, 106 reviewsVO Community 501 Midrise 2Bd/1.5Ba Large Open Deck
Cottage in Cudjoe Key
4.71 out of 5 average rating, 133 reviewsCalypso Cottage
Cottage in Cudjoe Key
4.89 out of 5 average rating, 142 reviewsATLANTIS...Ocean Front Cottage Retreat!
Other great vacation rentals in Cudjoe Key
Home in Marathon
4.91 out of 5 average rating, 11 reviews1 Free Night-Ask Us How - Tropical Private Home
Home in Big Pine Key
5 out of 5 average rating, 3 reviewsSecluded Waterfront Oasis in the Keys
Home in Marathon
5 out of 5 average rating, 17 reviewsLuxe Super Snapper-Heated Pool, Tiki, Dock, Lanai
Home in Marathon
4.98 out of 5 average rating, 53 reviewsWaterfront Oasis: Pool, Tiki Lounge, Dock & BBQ
Home in Cudjoe Key
4.79 out of 5 average rating, 24 reviewsWonderful Chalet - 20 miles from Key West
Vacation home in Cudjoe Key
4.8 out of 5 average rating, 30 reviewsCasa Del Sol 2/2 sleeps 6
Home in Marathon
4.98 out of 5 average rating, 41 reviewsOceanfront with Pool near Sombrero Beach
Camper/RV in Big Pine Key
4.9 out of 5 average rating, 61 reviewsHaving fun in the lower Keys
Quick stats about vacation rentals in Cudjoe Key
Total rentals
250 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
4.5K reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
110 properties allow pets
Rentals with a pool
190 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
What types of vacation rentals are available in Cudjoe Key?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Cudjoe Key. From over 10 cottage rentals to over 190 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
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 110 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.
Do house rentals in Cudjoe Key have wifi?
Absolutely! We offer over 190 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 Cudjoe Key house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 130 house rentals with pools in Cudjoe Key, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Cudjoe Key?
Cudjoe Key has more than 180 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Cudjoe Key?
Enhance your stay in our House Rentals with the most popular amenities: over 60 homes with a bbq area, over 30 homes with self check-in, over 190 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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