Beachfront vacation rentals in Cudjoe Key

Villa 5027 on Duck Key BOAT SLIP available

Boat slip available for an additional $100 per night. Ask about availability. This villa boasts breathtaking sunsets and is just minutes from watersports, charter fishing, waterfront restaurants, and local attractions, all while being surrounded by one of Duck Key’s most exclusive island neighborhoods with lush tropical landscaping. Duck Key is perfect for families or a serene couples retreat. Dine while watching spectacular sunsets from the rear deck, or explore the Middle Keys. No smoking/Pet

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!

*NEW* Private Beach, pool & fully loaded kitchen

Escape to paradise in our brand new, beautifully furnished Sun Life Vacation Homes beachfront oasis in the heart of Key Colony Beach, Florida, (some still call it Marathon). This luxurious two-bedroom, two-bathroom condominium invites you to experience the ultimate coastal retreat with private beach & pool access, tiki huts and BBQ grills. Come and experience the ultimate beachfront getaway at our Sun Life Vacation Homes, Key Colony Beach Club vacation rental. We recommend all guests purchas

Oceanside home 109, dock,kayaks,bikes,pool,fishing

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #109 and I also rent adjacent homes 111 and 107 in case you need more than one. We are 80 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

Latitudes-Ocean Front Pool

This tropical 6 bedroom 4 bath oceanfront home has a private heated salt water pool and huge outdoor living space. There is beach access, shared dock space and outdoor gazebo to watch sunsets. There is a 3rd story balcony that offers spectacular views of the sunrise and sunset. Bring up to a 24' boat or paddle out on one of the shared kayaks onsite. Fully equipped kitchen, linens, beach towels, a propane BBQ grill and 2 washer/dryers. This home is priced based on the number of guests.

Exquisite Oceanfront Paradise - Key Colony Beach

Stunning direct ocean views. Everything is brand new in this gorgeous condo with comfy king bed and fully equipped kitchen with full-size appliances and everything you need to cook and serve meals. Fast, free, reliable WiFi, and SmartTV to enjoy your favorite movies and shows. Heated pool and private sandy beach just steps away. Sunset Park next door is perfect for catching beautiful nightly sunsets. Centrally located to awesome Keys adventures just a few miles drive from the condo.

Beachside Unit 33-Private Tropical Beach Plus Pool

Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests (0-2 years old count as a guest). No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

Waterfront Villa & Sunset Views

Come and relax on your own veranda that overlooks the turquoise waters of the beautiful Duck Key. The outdoor living space is quiet and serene, making it a perfect place to unwind. Families and honeymooners alike can enjoy this island oasis. Centrally located at Mile Marker 61, Duck Key is just a short drive to Key West. Explore everything the Florida Keys have to offer or stay local to enjoy world-renowned restaurants, fishing, snorkeling, and diving. The opportunities are endless.

Vibrant Beachfront Villa

Welcome to Beachfront Villa that has recently been renovated. The 2 bedroom 1.5 bath luxury villa is located in the popular area of Duck key alongside of Hawks Cay Resort. Duck Key marina is located across the street where you can dock your boat or charter a boat for the day. Enjoy stunning sunset views from the back porch. Kitchen includes all amenities including silverware ,plates , cups , and pots. Linens and towels provided. *** Pets welcome with host approval and pet fee. ****

P01 - New 3 bed, 3 bath with private pool

This beautiful new home offers 3 bedrooms, 3 baths and a comfortable open floorplan. Additionally, this property boasts and abundance of fabulous outdoor living space and is ideally located minutes from Coco Plum Beach. - Maximum Occupancy: 6 guests (includes adults and children of any age) (*children of any age, including infants, count toward occupancy) - No day guests or visitors allowed above the advertised max. occupancy. - Parking: 3 vehicle max - 3 bedroom/3 bathroom

Hidden Beach Duplex, Best Place in Key West

Go to sleep and wake up smiling listening to the waves. Just 3 blocks from Duval Street; this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort. This is an extraordinary condo on an extraordinary property. This is nicest unit of 3 for rent at Hidden Beach. If you are discerning, this really is best place place to stay in Key West.