Cudjoe Key vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Cudjoe Key

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Superhost

Cottage in Cudjoe Key

4.92 out of 5 average rating, 130 reviews

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

Dec 28 – Jan 4

€ 771 per night
Guest favorite

Home in Key West

4.94 out of 5 average rating, 268 reviews

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

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Aug 4 – 11

€ 530 per night
Superhost

Home in Cudjoe Key

4.81 out of 5 average rating, 122 reviews

Ocean View 2/2 on Canal

Hurricane Ian did no damage This is a non-smoking, no pets, canal front home with a 35' sea wall. Ocean views from either deck. Vaulted great room. Fully equipped kitchen and linens with two private bed/bath suites offering privacy. The resort is gated and secure with plenty of amenities: a small tiki beach, marina, large pool, hot tub, pickle ball, tennis,laundry and general store. One time $113.00 resort fee Required to book: 1. verified identity 2. have positive reviews on AIrbnb

Jun 25 – Jul 2

€ 429 per night

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

Cudjoe Key house rentals

Guest favorite

Home in Marathon

4.9 out of 5 average rating, 155 reviews

Beachfront Villa - Florida Keys

Oct 5 – 12

€ 442 per night
Guest favorite

Home in Marathon

4.96 out of 5 average rating, 118 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Sep 16 – 23

€ 425 per night
Guest favorite

Home in Marathon

4.97 out of 5 average rating, 115 reviews

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

May 8 – 15

€ 627 per night
Guest favorite

Home in Marathon

4.99 out of 5 average rating, 103 reviews

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

Jan 22 – 29

€ 716 per night
Superhost

Home in Key Colony Beach

4.81 out of 5 average rating, 131 reviews

Waterview from three sides, Cabana Club, 30' Docks

Jan 5 – 12

€ 406 per night
Superhost

Home in Cudjoe Key

4.84 out of 5 average rating, 38 reviews

Relaxing Home in the Keys

Aug 31 – Sep 7

€ 229 per night
Guest favorite

Home in Cudjoe Key

4.94 out of 5 average rating, 16 reviews

May Extravaganza - Relax in Paradise!

May 24 – 31

€ 310 per night
Guest favorite

Home in Cudjoe Key

4.94 out of 5 average rating, 18 reviews

Conch Cabana in Paradise 23 miles outside Key West

Jun 7 – 14

€ 351 per night
Superhost

Home in Cudjoe Key

4.85 out of 5 average rating, 39 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Jun 4 – 11

€ 692 per night
Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 5 reviews

Venture Out -Million Dollar Island Resort

Nov 23 – 30

€ 355 per night
Superhost

Home in Cudjoe Key

4.83 out of 5 average rating, 24 reviews

Keys Island Villa - Venture Out Home 354

Sep 1 – 8

€ 402 per night
Superhost

Home in Cudjoe Key

4.83 out of 5 average rating, 6 reviews

Sailfish Haven

Mar 9 – 16

€ 320 per night

Cudjoe Key cottage rentals

Guest favorite

Cottage in Islamorada

4.85 out of 5 average rating, 124 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

Aug 22 – 29

€ 219 per night
Guest favorite

Cottage in Cudjoe Key

4.91 out of 5 average rating, 75 reviews

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

Mar 14 – 21

€ 962 per night
Superhost

Cottage in Cudjoe Key

4.84 out of 5 average rating, 31 reviews

Tidewater Views @ Venture Out - Waterfront

Nov 13 – 20

€ 404 per night
Superhost

Cottage in Key West

4.95 out of 5 average rating, 84 reviews

Mango Cottage 2 bedroom 2 bath with private pool

Jul 9 – 16

€ 645 per night
Guest favorite

Cottage in Marathon

4.95 out of 5 average rating, 20 reviews

Catch n' Relax Canalfront Cottage in Marathon

Oct 3 – 10

€ 323 per night
Guest favorite

Cottage in Islamorada

4.97 out of 5 average rating, 63 reviews

Islamorada 2BR, 1BA w/ heated pool and firepit

Nov 28 – Dec 5

€ 432 per night
Guest favorite

Cottage in Islamorada

4.94 out of 5 average rating, 16 reviews

Waterfront Cottage Walk to World Famous Lorelei

Sep 5 – 12

€ 289 per night
Guest favorite

Cottage in Islamorada

4.94 out of 5 average rating, 36 reviews

Islamorada bungalow 2 bed & pool

Oct 23 – 30

€ 447 per night
Superhost

Cottage in Key West

4.86 out of 5 average rating, 28 reviews

Namaste: A blissful one bedroom cottage

May 16 – 23

€ 629 per night
Guest favorite

Cottage in Key West

4.89 out of 5 average rating, 90 reviews

The Dancing Rooster

Jul 31 – Aug 7

€ 612 per night
Guest favorite

Cottage in Marathon

4.96 out of 5 average rating, 25 reviews

WATER FRONT COTTAGE W/ MOTHER IN LAW TREETOP SUITE

Jul 26 – Aug 2

€ 575 per night

Cottage in Key West

4.74 out of 5 average rating, 336 reviews

1 bedroom Cottage

Apr 6 – 13

€ 371 per night

Other great vacation rentals in Cudjoe Key

Guest favorite

Apartment in Key West

4.97 out of 5 average rating, 234 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Aug 20 – 27

€ 378 per night
Guest favorite

Guesthouse in Key West

4.93 out of 5 average rating, 521 reviews

Old Town - Room Opens to Pool and Garden

Jun 12 – 19

€ 367 per night
Guest favorite

Guest suite in Tavernier

4.98 out of 5 average rating, 245 reviews

Island Get Away

Aug 25 – Sep 1

€ 181 per night
Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 88 reviews

Breezy pines 28 foot 5th wheel trailer .

Nov 20 – 27

€ 128 per night
Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 3 reviews

Latitudes-Ocean Front Pool

Aug 31 – Sep 7

€ 774 per night
Guest favorite

Vacation home in Cudjoe Key

5.0 out of 5 average rating, 30 reviews

Beautiful Cottage & Amenities in Gated Community

Jun 21 – 28

€ 350 per night
Superhost

Home in Cudjoe Key

4.82 out of 5 average rating, 67 reviews

Tree Top Paradise

Nov 5 – 12

€ 309 per night
Superhost

Home in Upper Sugarloaf Key

4.86 out of 5 average rating, 43 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

Dec 6 – 13

€ 1,024 per night
Superhost

Home in Cudjoe Key

4.81 out of 5 average rating, 32 reviews

Keys getaway

Oct 13 – 20

€ 351 per night
Superhost

Home in Cudjoe Key

4.87 out of 5 average rating, 68 reviews

Island Oasis ~ YOUR Paradise Awaits!

Mar 14 – 21

€ 354 per night
Superhost

Home in Cudjoe Key

4.83 out of 5 average rating, 18 reviews

Little gem in a safe resort with amenities

Aug 25 – Sep 1

€ 292 per night
Guest favorite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 81 reviews

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

May 3 – 10

€ 197 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

3.7K reviews

Nightly prices starting at

€ 83 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 150 house rentals to over 10 cottage 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 $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 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 30 homes with self check-in, over 150 homes with wifi, 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