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

*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

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.

Private Beach in Marathons Key Colony Beach
Atlantic Ocean location with a beautiful ocean view. The beach is private for sunbathing, fishing, diving, and snorkeling. The sea life off the beach is abundant. Watching the boats come in and out of Vaca Cut is very cool. In addition to the onsite pool there is a Tiki Hut, beachside barbecue area, and a beautiful grass lawn. Being on the third floor offers beautiful ocean views. Please see my host guidebook for detailed info on a few of the local attractions including fav restaurants.

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.

Oceanfront Sunrise Condo Private Beach Heated Pool
Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

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.

Ocean Oasis!OceanView-Private Beach/Pool/TikiHuts
Welcome to Ocean Oasis, your tropical haven in Marathon, Florida! Our stunning 2-bedroom, 2-bathroom condo is located at 501 E Ocean Dr, Marathon, FL 33050. Ocean Oasis offers the ultimate beachfront retreat, with a King-sized bed in the master bedroom and two full-sized beds in the second bedroom, comfortably sleeping six. The spacious balcony boasts breathtaking views of the ocean and pool, perfect for sipping morning coffee or enjoying a sunset cocktail. No Pets Allowed.

Lighthouse - 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. Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings.

Hidden Beach unit 1 The Perfect Place to stay
This place is extraordinary. There is nothing like it in Key West. 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.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

Beachside Unit 39 Tiki Huts, Private Beach & Pool
Unit 39 Details: Second Floor Unit, Tub with 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 beachfront rentals in Cudjoe Key
Pet-friendly beachfront home rentals

Powell Family Resort

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

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Charming Beach House directly ON the beach

LARGE LOT & RV | Fishermen Camp

7 Mile Ocean Bliss

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

Private pool and beach: "Sea Isle #8" on YouTube

Oceanfront Balcony King, Isla Bella, Beach Resort

Ocean front with private beach and pool!

Port Antigua NEW lux apart

Oceanfront Key West Condo

Luxury Retreat in the Keys | Boat Dock | Beach

Tranquil Island Studio - Perfect for Relaxation
Private beachfront home rentals

Beachside Unit 36 Private Patio & Beach Plus Pool

Beachside Unit 12- Pool, Private Beach & Tiki Huts

Key Colony Beach Luxury Condo, New Modern Interior

Oceanfront Breeze, Stunning Views, Beach/Pool

Keys Breeze Ocean View Condo & Pool - Key Colony

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

Keys Time Condo Oceanfront Complex Heated Pool

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 £157 per night before taxes and fees

Verified guest reviews
Over 600 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Wifi availability
10 of Cudjoe Key holiday rentals include wifi 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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