We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Some info has been automatically translated. Show original language

Airbnb your place

House vacation rentals in Cudjoe Key

Find and book unique houses on Airbnb

Top-rated house rentals in Cudjoe Key

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

0 of 0 items showing

1 of 3 pages

Home in Cudjoe Key

4.9 out of 5 average rating, 40 reviews

Cozy 2 br/2 bath home in Cudjoe

Discover a slice of Floridian paradise in our charming 2b/2bath located in Venture Out community, Cudjoe Key. Two bedrooms and an outdoor patio promise relaxation, while community amenities such as a pool, tennis courts, and kids' playground are available. A place to experience the laid-back Florida lifestyle and create unforgettable memories. Book your stay with us today and come live the dream in Cudjoe Key! ****Upon entry, there is a one-time community fee paid at the gate check-in: $125.

Home in Key West

4.95 out of 5 average rating, 308 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.

Home in Cudjoe Key

4.92 out of 5 average rating, 38 reviews

Private Ocean Oasis by Key West, Florida

Beautiful stilted two bedroom/two bathroom vacation home awaits your arrival. Break taking views of the Atlantic Ocean are picture worthy. This home hosts a 36' seawall on a wide canal. Dock equipped with fishing cleaning station, cleats, swim ladder, outdoor shower and bait freezer. King-, queen-, full- and twin-size mattresses provide comfortable sleeping accommodations for all guests. Extensive indoor and outdoor furniture allow for all to relax, recharge and enjoy their time in paradise!!

Home in Cudjoe Key

4.9 out of 5 average rating, 105 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Home in Key Colony Beach

4.94 out of 5 average rating, 101 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Home in Marathon

4.94 out of 5 average rating, 158 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in the beautiful Florida Keys! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Home in Cudjoe Key

4.97 out of 5 average rating, 140 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Home in Marathon

4.99 out of 5 average rating, 121 reviews

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

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Home in Cudjoe Key

4.82 out of 5 average rating, 248 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Home in Key Colony Beach

4.93 out of 5 average rating, 101 reviews

Paradise in Key Colony Beach + Cabana Club

Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

Home in Cudjoe Key

4.92 out of 5 average rating, 156 reviews

Paradise and Cudjoe Bay

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."

Home in Key Colony Beach

4.98 out of 5 average rating, 110 reviews

Super Nov. Savings! Key Colony Beach, Cabana Club

Second Wind is on the 9th Street canal, a beautiful corner lot with exceptional views and ocean breezes. Cabana Club! Dockage for a 20 ft boat. A two-minute walk to Sunset Park in the wonderful community of Key Colony Beach! Open floor plan with cathedral ceiling, large deck with seating for six overlooking the pristine turquoise canal. It is the perfect place for your Florida Keys getaway!

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Cudjoe Key house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Cudjoe Key

4.89 out of 5 average rating, 18 reviews

Pelican's Roost, Waterfront comfort at Venture Out

Home in Marathon

5 out of 5 average rating, 36 reviews

100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

Home in Little Torch Key

4.87 out of 5 average rating, 67 reviews

Waterfront Beach House with Dock & Heated Pool!

Home in Marathon

4.98 out of 5 average rating, 53 reviews

Waterfront Oasis: Pool, Tiki Lounge, Dock & BBQ

Home in Cudjoe Key

4.79 out of 5 average rating, 24 reviews

Wonderful Chalet - 20 miles from Key West

Home in Cudjoe Key

4.85 out of 5 average rating, 26 reviews

Lower Keys Paradise

Home in Marathon

4.98 out of 5 average rating, 132 reviews

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

Home in Key Colony Beach

4.88 out of 5 average rating, 123 reviews

Tiki Time

Weekly house rentals

Home in Marathon

5 out of 5 average rating, 27 reviews

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

Home in Marathon

4.91 out of 5 average rating, 11 reviews

1 Free Night-Ask Us How - Tropical Private Home

Home in Big Pine Key

4.92 out of 5 average rating, 13 reviews

key Deer Retreat/direct gulf access/hot tub

Home in Big Pine Key

5 out of 5 average rating, 3 reviews

Secluded Waterfront Oasis in the Keys

Home in Marathon

5 out of 5 average rating, 17 reviews

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

Home in Cudjoe Key

4.83 out of 5 average rating, 41 reviews

Relaxing Home in the Keys

Home in Cudjoe Key

4.94 out of 5 average rating, 18 reviews

Sea Turtle Cove

Home in Marathon

4.98 out of 5 average rating, 41 reviews

Oceanfront with Pool near Sombrero Beach

Private house rentals

Home in Marathon

5 out of 5 average rating, 22 reviews

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

Home in Marathon

4.88 out of 5 average rating, 33 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

Home in Marathon

4.96 out of 5 average rating, 49 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Home in Big Pine Key

4.9 out of 5 average rating, 69 reviews

Fishermen's Paradise | Pool, dock, gorgeous home

Home in Key Colony Beach

4.95 out of 5 average rating, 19 reviews

Water, Water Everywhere! "The Wheel House"

Home in Marathon

5 out of 5 average rating, 18 reviews

Off the Hook~ Luxe Pool Home, Kayaks & Bikes!

Home in Marathon

5 out of 5 average rating, 20 reviews

Coco Plum Paradise - Marathon 5 BR 4 BA Waterfront

Home in Big Pine Key

4.86 out of 5 average rating, 7 reviews

Island time on Big Pine

Quick stats about house rentals in Cudjoe Key

Total rentals
190 properties
Nightly prices starting at
$120 before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
180 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
130 properties have a pool

Destinations to explore