
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.

*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
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Bright Cheery Condo, Ocean Views in Key Colony
Beautifully renovated condo in Key Colony Beach. with one king bed, well equipped kitchen with full-size appliances & everything you need to cook and serve meals. New A/C for great cooling. Renovated bathroom with walk-in shower, plenty of counter space and storage. Free & reliable WiFi with a private back balcony with chairs and table. Enjoy the heated pool & private sandy beach just steps away from your condo door. Sunset Park is next door, great for catching beautiful Florida Keys sunsets.
BeachWalkabilityGetting around

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!
Experience the relaxing setting of this 4BR 4.5Bath home, ideally situated in the picturesque waterfront neighborhood of Marathon, FL. Discover the area's scenic beauty and a diverse selection of water activities, attractions, and landmarks. After a day of exploring, return to our home for a rejuvenating stay. ✔ 4 Comfy BRs ✔ Open Design Living ✔ Full Kitchen ✔ Balcony ✔ Backyard (Pool, Games, BBQ, Lounges, Dining) ✔ 73-Foot Dock ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!
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New Private 4/3 Single Family - Kayaks & Bicycles+
Blue Treasure at Sombrero Beach is a 2020 built single-family home in a private community within walking distance to the beautiful Sombrero beach and 5 minute boat ride to the ocean. This house is a private fully equipped 4/3 that has three king memory foam beds and one queen memory foam & queen sofa memory foam. All the rooms have a TV w/ cable & Netflix. We also have a separate downstairs area that we provide kayaks, paddle boards, and bicycles at no additional cost. License #:VACA-20-150
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Cabana Club Condo: Key Colony Beach, FL
Located on the Atlantic Ocean in the middle keys. Accommodations for up to 10 people. Waking up to the sounds of ocean waves and the beautiful waters of the Florida Keys is breath taking. Very few are on a private beach. The unit is very spacious and well kept. Large master closet for storage. Private entrance and Cabana Club access during operating hours: ( Monday 10-5, Tuesday-Sunday 10-7 ). New furnishings, full kitchen, clothes washer and dryer. Minimum one week rental, seven nights.
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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.
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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!
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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.
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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
BeachWalkabilityKitchen

Villa 5027 on Duck Key BOAT SLIP available
Boat slip available for additional $100 a night. 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.
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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.”
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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.
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Popular amenities for Cudjoe Key beachfront rentals
Pet-friendly beachfront home rentals

Beach Home and Boater’s Paradise Sombrero
LocationLong stayKitchen

Powell Family Resort
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OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS
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Coco Plum Beach Paradise w Heated Pool & Boat Slip
HospitalityLocation

Charming Beach House directly ON the beach
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Key West Luxury Houseboat at Yacht Club Resort
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SeaEsta! Bring your boat & 1 block to the beach!
WalkabilityBeachQuiet

Vibrant Beachfront Villa
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Beachfront home rentals with a pool

Seaside Villa~ Charming Beachfront Condo w/ Pool!
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Grouper Getaway @ Ocean Isles Fishing Village
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RV In The Keys | Tropical Retreat
BeachConditionTV

Beachfront Condo on Coco Plum Beach w/heated pool
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Private Beach in Marathons Key Colony Beach
WalkabilityBeachFamily

Florida Keys Getaway w/ Stunning Ocean Views
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Beach Front
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Canal/Dock - Cabana Club - Pickleball - Remodeled
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Private beachfront home rentals

Spectacular 2BR Oceanfront Dog Friendly | Dock
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Stunning tropical Ocean view condo
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Key Colony Beach Luxury Condo, New Modern Interior
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Key Lime Condo, Key Colony Beach Oceanfront & Pool
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Keys Breeze Ocean View Condo & Pool - Key Colony
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Paradise awaits.
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Poolside 2 Bdrm in Oceanfront Complex, Key Colony
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Beachside Unit 27 - The Beach is Calling You!
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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 $314 AUD per night before taxes and fees

Verified guest reviews
Over 480 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!
Destinations to explore
- Villa rentals Cudjoe Key
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- Rentals with a kayak Cudjoe Key
- Waterfront rentals Cudjoe Key
- Pet-friendly rentals Cudjoe Key
- Rentals with a hot tub Cudjoe Key
- Rentals with a washing machine and dryer Cudjoe Key
- Cottage rentals Cudjoe Key
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- Beachfront rentals Monroe County
- Beachfront rentals Florida
- Beachfront rentals United States
- Sombrero Beach
- Smathers Beach
- Bahia Honda State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Southernmost Point
- Conch Key
- Dolphin Research Center
- Key West Butterfly & Nature Conservatory
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Key West Aquarium
- Curry Hammock State Park





