
Beachfront vacation 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

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.

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.

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.

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!

The Lighthouse - Beach Houses Key West
If you’re reading this, you’re already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning bird’s-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beach—an ideal spot for peaceful mornings and ocean breezes.

Stylish Anglers Retreat Poolside and Ocean U16
Embrace the charm of the Keys in our serene escape for couples or families. Nestled just steps from a heated pool and the ocean, this marine-themed retreat offers king comfort, a cozy sofa sleeper, and a screened balcony for intimate evenings. Dive into local adventures with available beach gear, or unwind in our airy space, boasting a fully equipped kitchen and tasteful decor. Ideal for those seeking a blend of relaxation and oceanic exploration, it's your perfect coastal haven.

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 37 - Come Relax on the Atlantic!
Unit 37 Details: Second Floor, Walk-in shower, Two Queen Beds, Twin Sofa Sleeper, 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. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.” Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean.
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

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

Oceanfront Breeze, Stunning Views, Beach/Pool

Keys Breeze Ocean View Condo & Pool - Key Colony

Ocean front with private beach and pool!

Amazing Beachfront Studio w/ Stunning Gulf Views!

Sandy Beach Just Steps Away

Steps to the Beach Condo - Key Colony Beach

Seaport Serenity-Beach-Pool-King-BBQ-ExtraEntrance

NEW-Luxury Waterfront Island Home-BEACH, Pool Dock
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

Sunny Beachfront Condo - Key Colony Beach & Pool

Keys Time Condo Oceanfront Complex Heated Pool

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

Ocean Blue Condo, Key Colony Beach Heated Pool

Tropical Beachfront Condo Key Colony Beach & Pool
Quick stats about beachfront rentals in Cudjoe Key

Total vacation rentals
Explore 10 vacation rentals in Cudjoe Key

Nightly prices starting at
Cudjoe Key vacation rentals start at $314 CAD per night before taxes and fees

Verified guest reviews
Over 440 verified reviews to help you choose

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

Vacation rentals with a pool
10 properties feature pools

Wifi availability
10 of Cudjoe Key vacation 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
- Conch Key
- Bahia Honda State Park
- Long Beach
- Fort Zachary Taylor Historic State Park
- Sunset Park
- Florida Keys Aquarium Encounters
- Dolphin Research Center
- Southernmost Point
- Seven Mile Bridge
- Key West Butterfly & Nature Conservatory
- The Turtle Hospital
- Ernest Hemingway Home & Museum
- Boyd's Key West Campground
- Key West Lighthouse Museum




