
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.

RV In The Keys | Tropical Retreat
Tropical retreat in the heart of Florida Keys. Relax in this fully furnished private & clean RV with parking just 30 miles from Key West. Enjoy breezy indoor/outdoor living with a fold-down patio, 2 TVs, full kitchen, bathroom, pantry. Outside seating g with awning. Nestled in a local RV park w/ pool, fish station, and coin laundry. Vacation here & swim in the ocean —Next to Pine Channel in Big Pine Key and 10 miles to Bahai Honda State Park. Walk to groceries, Walgreens, restaurants. Staycation

*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.

Ocean Front Studio private Sandy Beach in Key West
Studio unit with fridge, microwave, settings for 2 and a king sized bed. Doors that open to a balcony overlooking the Atlantic Ocean. There is pool, hot tub, and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street. The resort is located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. There is free garage parking with the room. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy air conditioning.

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.

Beach Club Tidal Wave-Beach/Pool
Welcome to your perfect island getaway! This charming 2-bedroom condo is located just steps from the ocean at Key Colony Beach Club. With a King bed in the primary bedroom and two Twin beds in the second room, it’s the ideal retreat for families, couples, or friends seeking comfort and convenience. Enjoy bright, beachy interiors, a fully equipped kitchen, and easy access to the beach, local restaurants, and outdoor activities. -No pets are allowed. -You must be 25 years or older to rent.

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.

Paradise found! Sea-Esta Condo beach and pool.
Sea-Esta is located on the Atlantic Ocean with a private white sandy beach. If the ocean isn’t calling you, Sea-Esta by the heated pool to cool off and work on your tan. Or, Sea-Esta in your master bedroom with its king-size bed and ocean views from its small deck. Sea-Esta under the shade of the lush landscaping that Sea Isle has to offer. Walking distance to Sunset Park, 3 par golf course, pickleball, tennis, bocce ball, and playground. Safe bike/walking paths throughout Key Colony.

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.

Coastal Key Colony Beach Condo, Oceanfront Complex
Lovely coastal Keys studio condo in Key Colony Beach oceanfront complex with heated pool and private beach. Unit #17 has new beds with memory foam mattress toppers and renovated kitchen with granite countertops stocked with everything needed to cook a complete meal (dishes, cookware, appliances and of course blender, etc). Relax on the back balcony and enjoy sunsets from Sunset Park right next door. Private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

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!

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.
Popular amenities for beachfront rentals in Cudjoe Key
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

Sale! Lux Home, Walk to Beach, 90' Dock, Pool

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

Key West Luxury Houseboat at Yacht Club Resort

New Private 4/3 Single Family - Kayaks & Bicycles+

Vibrant Beachfront Villa
Beachfront home rentals with a pool

Marathon Oceanfront Suite | King Bed + Kitchenette

Oceanfront Breeze, Stunning Views, Beach/Pool

Keys Breeze Ocean View Condo & Pool - Key Colony

Oceanfront Balcony King, Isla Bella, Beach Resort

Ocean front with private beach and pool!

Amazing Beachfront Studio w/ Stunning Gulf Views!

Sombrero Sunrise 5BR/5BA, 1/2 mile to Sombrero Bea

Sandy Beach Just Steps Away
Private beachfront home rentals

Oceanfront Sunrise Condo Private Beach Heated Pool

2 Bedroom Oceanfront Complex, Key Colony Beach

Beachside Unit 14 - Brand New Kitchen and Bathroom

Key Lime Condo, Key Colony Beach Oceanfront & Pool

Keys Time Condo Oceanfront Complex Heated Pool

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

Exquisite Luxury Oceanfront Complex Key Colony

Ocean Blue Condo, Key Colony Beach Heated Pool
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 € 194 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 & 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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- Beachfront rentals Monroe County
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- Beachfront rentals United States
- Sombrero Beach
- Smathers Beach
- Calusa Beach & Loggerhead Beach
- Long Beach
- Conch Key
- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- Sunset Park
- Ernest Hemingway Home & Museum
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Dolphin Research Center
- Southernmost Point
- Seven Mile Bridge
- Boyd's Key West Campground
- Key West Butterfly & Nature Conservatory
- Key West Lighthouse Museum




