Cudjoe Key vacation rentals

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Popular amenities for Cudjoe Key vacation rentals

Stay near Cudjoe Key's top sights

Sugarloaf Key / Key West KOA Holiday3 locals recommend
Mangrove Mama's21 locals recommend
Square Grouper Bar and Grill47 locals recommend
My New Joint27 locals recommend
Cudjoe Sales Fishermen's Warehouse4 locals recommend
Fanci Seafood3 locals recommend

Other great vacation rentals in Cudjoe Key

Guest favorite

Home in Key West

4.94 out of 5 average rating, 271 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Feb 20 – 27

G$117,832 GYD per night
Guest favorite

Home in Marathon

4.99 out of 5 average rating, 106 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

Dec 2 – 9

G$156,154 GYD per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 117 reviews

Marathon one-level home on the Marina - with slip!

Nov 10 – 17

G$113,330 GYD per night
Superhost

Home in Cudjoe Key

4.85 out of 5 average rating, 39 reviews

Relaxing Home in the Keys

Aug 23 – 30

G$46,886 GYD per night
Superhost

Home in Cudjoe Key

4.86 out of 5 average rating, 42 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Aug 29 – Sep 5

G$143,105 GYD per night
Guest favorite

Home in Cudjoe Key

4.95 out of 5 average rating, 19 reviews

Conch Cabana in Paradise 23 miles outside Key West

Dec 13 – 20

G$63,760 GYD per night
Guest favorite

Home in Ramrod Key

5.0 out of 5 average rating, 6 reviews

Casa Sirena | Canalfront 3BD/2BA|FLKeys|POOL|DOCK

Mar 7 – 14

G$60,620 GYD per night
Superhost

Home in Cudjoe Key

4.83 out of 5 average rating, 48 reviews

Spanish Queen @Venture Out

Sep 3 – 10

G$79,800 GYD per night

Cudjoe Key cottage rentals

Superhost

Cottage in Cudjoe Key

4.91 out of 5 average rating, 53 reviews

Turtle Cove Views @ Venture Out - Waterfront

Oct 19 – 26

G$86,287 GYD per night
Guest favorite

Cottage in Cudjoe Key

4.91 out of 5 average rating, 78 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Mar 15 – 22

G$190,672 GYD per night
Guest favorite

Cottage in Key West

4.95 out of 5 average rating, 84 reviews

Mango Cottage 2 bedroom 2 bath with private pool

Sep 13 – 20

G$140,775 GYD per night
Guest favorite

Cottage in Islamorada

4.94 out of 5 average rating, 16 reviews

Waterfront Cottage Walk to World Famous Lorelei

Sep 6 – 13

G$56,526 GYD per night
Guest favorite

Cottage in Islamorada

4.97 out of 5 average rating, 65 reviews

Key Lime Cottage 2br 1ba w/pool

Oct 25 – Nov 1

G$75,359 GYD per night
Guest favorite

Cottage in Marathon

4.95 out of 5 average rating, 22 reviews

Catch n' Relax Canalfront Cottage in Marathon

Jul 31 – Aug 7

G$60,960 GYD per night
Guest favorite

Cottage in Islamorada

4.95 out of 5 average rating, 40 reviews

Islamorada bungalow 2 bed & pool

Dec 7 – 14

G$95,534 GYD per night
Superhost

Cottage in Key West

4.86 out of 5 average rating, 29 reviews

Namaste: A blissful one bedroom cottage

Jul 31 – Aug 7

G$133,431 GYD per night

Other great vacation rentals in Cudjoe Key

Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 88 reviews

Breezy pines 28 foot 5th wheel trailer .

Apr 6 – 13

G$31,067 GYD per night
Guest favorite

Vacation home in Cudjoe Key

5.0 out of 5 average rating, 36 reviews

Beautiful Cottage & Amenities in Gated Community

Nov 14 – 21

G$63,190 GYD per night
Superhost

Home in Cudjoe Key

4.86 out of 5 average rating, 28 reviews

Keys Island Villa - Venture Out Home 354

Mar 31 – Apr 7

G$147,094 GYD per night
Guest favorite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 82 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

May 25 – Jun 1

G$40,194 GYD per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 32 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Apr 19 – 26

G$130,242 GYD per night
Guest favorite

Camper/RV in Big Pine Key

4.93 out of 5 average rating, 40 reviews

Having fun in the lower Keys

May 9 – 16

G$34,318 GYD per night
Guest favorite

Condo in Key West

4.99 out of 5 average rating, 84 reviews

Hidden Beach Duplex, Best Place in Key West

Oct 4 – 11

G$133,793 GYD per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 34 reviews

The Gulf Cottage at Marathon Key

Jun 29 – Jul 6

G$32,441 GYD per night

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

    G$22,927 GYD 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

  • 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 150 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 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.

  • 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 150 homes with wifi, over 30 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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