Waterfront holiday rentals in Cudjoe Key

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Cudjoe Key

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

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Guest favourite

Townhouse in Marathon

4.97 out of 5 average rating, 172 reviews

Marathon Keys Coral Lagoon Unit 2 Waterfront Villa

*Currently the seawall repair is not affecting our side of the property, our view is unobstructed and not affected. Also, our marina is 100% open and operational should you need to rent a slip during your stay Welcome to paradise! We are proud to offer you one of the nicest waterfront units in Coral Lagoon! Please Note: For your safety, the entire house is sanitized prior to your arrival. Along with our standard cleaning practices we have a local company that comes in and fogs the entire house

Guest favourite

Villa in Marathon

5 out of 5 average rating, 11 reviews

Waterfront Home w/Dock, Pool, Bikes & SO MUCH MORE

Looking for the perfect home for your next Florida Keys vacation? Our Waterfront home with over 30 feet of dock space is Just a short boat ride out to open water for a day of fishing, snorkeling, or cruising around. Our home features your own private dock & private pool... complete with chaise lounges, outdoor dining, gas grill, Adirondack chairs, fish cleaning station, bait freezer & so much more! Lastly, everyone is sure to enjoy water views & sunsets from our balcony that never disappoint.

Superhost

Cottage in Cudjoe Key

4.86 out of 5 average rating, 36 reviews

Tidewater Views at Venture Out

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** TIDEWATER VIEWS is a cozy 800 square foot cottage that has everything you want for the perfect tropical vacation: open water views from a covered porch, a private 35-foot boat slip, kayaks, bikes and access to the wonderful amenities at Venture Out Resort: a heated 80-foot pool with large Jacuzzi and Kiddie Pool,

Superhost

Home in Marathon

5 out of 5 average rating, 3 reviews

Waterfront Oasis3/2 Direct Ocean

Welcome to our stunning vacation rental property located on the waters of the ocean, where you can enjoy the ultimate tropical getaway. Our property boasts of an exceptional location, featuring a private dock that provides direct access to the ocean. This beautifully furnished property has three spacious and comfortable bedrooms that can accommodate up to eight guests, making it perfect for families or friends. The two modern bathrooms are fully equipped with all the necessary amenities

Guest favourite

Home in Marathon

5 out of 5 average rating, 33 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Guest favourite

Cottage in Little Torch Key

4.9 out of 5 average rating, 167 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Guest favourite

Home in Key Colony Beach

4.95 out of 5 average rating, 111 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.

Guest favourite

Apartment in Key West

4.88 out of 5 average rating, 146 reviews

Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"

Enjoy true space in Key West! This 1,200 sq ft waterfront condo offers a full kitchen, dining area, living room, 2 bedrooms, and a private balcony—so much more than a hotel. Bring your boat—dockage is included with water, power, and a fish cleaning station. Relax by the heated pool or grill out at the tiki area. Walk or bike to Duval Street, the Seaport, Hemingway House, and more—less than 1 mile away. Pet-friendly, free on-site parking, and just 10 minutes from EYW airport.

Guest favourite

Home in Marathon

5 out of 5 average rating, 34 reviews

Amazing Bayfront New House with Dock and Pool!

NEW TO MARKET AND AVAILABLE FOR LOBSTER MINI SEASON!!! This new construction has everything. This concrete house is waterfront with great views of Bonefish Bay. The 70 foot dock is built in 10-12 foot water. It is frequented by manatee, dolphin, and numerous mangrove snapper. The large heated pool is surrounded by Turkish marble pavers that are cool to your feet. House has double master suites with en suite bathrooms and every necessity to make our home feel like yours.

Guest favourite

Townhouse in Marathon

4.85 out of 5 average rating, 105 reviews

Waterfront Duck Key Villa - Sleeps 8 (7058)

BEST VIEW IN DUCK KEY!!!! Waterfront Villa at the heart of the Florida Keys - Duck Key Florida. Beautiful location with easy access to both the Atlantic Ocean and the Gulf of Mexico. Come check us out and see for yourself what the exclusive Duck Key area has to offer. DOCK INCLUDED-35 Foot. Conveniently behind the village! The Village at Hawks Cay Villas by KeysCaribbean are not affiliated with the Hawks Cay Resort; our guests do not have access to hotel amenities.

Superhost

Home in Marathon

4.69 out of 5 average rating, 16 reviews

#7 Waterfront 4Bed 3Bath Pool Home

🌸Home #7 "BEACHY🏖KEEN" Full WATERFRONT View over the docks and beach and Ocean!🌸 Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Cooled Private Swimming Pool 🤿and BBQ Patio. Includes Private Guest Beach🏖 with Kayaks and Paddle boards and Private powered ⛵Boat Dock right on the Gulf of Mexico! 🌅🥂 Kick back and completely🍷 relax in our Beautiful and 🍹comfortable home! Perfect for 🍻Adults and kids of all Ages!

Guest favourite

Home in Marathon

4.89 out of 5 average rating, 160 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

Welcome to our beautiful waterfront home in Marathon! Our smoke-free property is modern, clean and features a 37ft long concrete dock, perfect for boating and fishing enthusiasts. With easy access to the movie theater, Sombrero Beach, Turtle Hospital, Publix, Walgreens, and delicious restaurants, you'll have everything you need right at your fingertips. We can't wait for you to experience the peacefulness and convenience of our lovely home.