
Beachfront holiday rental in Cudjoe Key
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Top-rated beachfront accommodation in Cudjoe Key
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.

Luna Light ~ Waterfront ~ Pool ~ Dock ~ Views!
Bring your family to the stylish 4BR 4.5Bath home in a tranquil waterfront area, and enjoy an unforgettable stay with your loved ones. Explore nearby attractions from this prime location, or spend the day soaking up the sun by the pool, fishing from the dock, savoring tasty BBQs, and much more! ✔ 4 Comfortable BRs ✔ Open Design Living ✔ Full Kitchen ✔ Outdoors (Heated Pool, Lounges, Dining, Games) ✔ Dock ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking (4 Cars + Trailer) ✔ Ev Charger See more bel

Villa 5027 on Duck Key BOAT SLIP available
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

Grassy Key Ocean Front Beach House
HEATED POOL $150 weekly. Experience relaxed island luxury with no neighbors within a block of the property, located on Grassy Key in the Middle Keys. Perched directly on the Atlantic with an unobstructed view, the property sits on private acreage and was designed to maximize the ocean panorama from every level. Whether you want to watch sunrise from the balcony, dine under the tiki hut, beside the oceanfront pool while listening to the surf, this is a place to reconnect with family and friends.

Grouper Getaway @ Ocean Isles Fishing Village
Escape to paradise at the Grouper Getaway located at Ocean Isles Fishing Village in Marathon Key, FL. This beautiful brand new fully furnished 1 bed/2 bath studio townhouse, offers a central location and an array of luxurious amenities for a truly unforgettable vacation. Steps away from the the Atlantic Ocean, enjoy the largest pool in Marathon with clear views of the VACA Cut boat traffic and the Sombrero Light House. Enjoy fishing, paddle boarding, kayaking, tiki huts, beach, and grills.

Palm - Beach Houses Key West
If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Experience the charm of our recently renovated, one-of-a-kind two-bedroom beach bungalow, nestled right on the shore. Enjoy breathtaking ocean views from your private deck, relax on the sandy beach, and soak in the tropical ambiance. This family-friendly retreat offers the perfect setting to make you feel like you’re on your very own private island.

Oceanside home 111, 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 #111 and I also rent adjacent homes 109 and 107 in case you need more than one. We are 40 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.

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!

Beautiful Beachfront Villa w/ Pool/Tiki/Dock
Beautiful Beachfront home located directly across the street from famous Sombrero Beach, with heated pool & Tiki Bar. Large wrap around balconies provides stunning beach views, sunrises & sunsets for relaxation. It boasts open floor plan with a large entertainment area that includes a gorgeous Olhausen Pool table, large bedrooms & the master bath is also a steam room. A 45' dock & spacious yard is great for entertaining or barbecuing. Pool Heater is available for an additional fee.

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.

Beachside Unit 33-Private Tropical Beach Plus Pool
Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests, 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.”

Houseboat Getaway In Marathon
Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.
Popular amenities for Cudjoe Key beachfront rentals
Pet-friendly beachfront home rentals

Beach Home and Boater’s Paradise Sombrero

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

Coco Plum Beach Paradise w Heated Pool & Boat Slip

Charming Beach House directly ON the beach

RV In The Keys | Tropical Retreat

Key West Luxury Houseboat at Yacht Club Resort

New Private 4/3 Single Family - Kayaks & Bicycles+
Beachfront home rentals with a pool

Wreckers House King Room - Adults Only

Stunning tropical Ocean view condo

Oceanfront Breeze, Stunning Views, Beach/Pool

Modern Beachfront Steps to Beach/Pool, Key Colony

Oceanfront Balcony King, Isla Bella, Beach Resort

Amazing Beachfront Studio w/ Stunning Gulf Views!

Oceanfront Key West Condo

Beachside Unit 27 - The Beach is Calling You!
Private beachfront home rentals

Beachside Unit 36 Private Patio & Beach Plus Pool

Oceanfront Sunrise Condo Private Beach Heated Pool

Beachside Unit 22 - Private Beach on Atlantic

2 Bedroom Oceanfront Complex, Key Colony Beach

Key Colony Beach Luxury Condo, New Modern Interior

Sunny Beachfront Condo - Key Colony Beach & Pool

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

Exquisite Luxury Oceanfront Complex Key Colony
Quick stats about beachfront rentals in Cudjoe Key

Total holiday rentals
Explore 10 holiday rentals in Cudjoe Key

Nightly prices starting at
Cudjoe Key holiday rentals start at $402 NZD per night before taxes and fees

Verified guest reviews
Over 440 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Wi-Fi availability
10 of Cudjoe Key holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Cudjoe Key rentals

4.9 Average rating
Cudjoe Key stays are highly rated by guests—averaging 4.9 out of 5!
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- Beachfront rentals Monroe County
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- Beachfront rentals United States
- Sombrero Beach
- Smathers Beach
- Long Beach
- Bahia Honda State Park
- Conch Key
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Sunset Park
- Dolphin Research Center
- Key West Lighthouse Museum
- Florida Keys Aquarium Encounters
- Key West Butterfly & Nature Conservatory
- The Turtle Hospital
- Boyd's Key West Campground
- Southernmost Point
- Calusa Beach & Loggerhead Beach




