
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

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 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.

Lagoona-Matata
A truly magical place "Lagoona-Matata" sits on the edge of Vaca Cut showcasing fabulous views of the Gulf. The outdoor area flows from the patio to the pool deck, private sandy beach, tidal pool and then to the pier dock. "Vaca Cut" is a fast-moving body of water from incoming to outgoing tides with fish of every kind moving through that makes fishing from the dock great entertainment. The continuous plethora of sea life in the lagoon makes this property an experience unlike any other.

Exquisite Oceanfront Paradise - Key Colony Beach
Stunning direct ocean views. Everything is brand new in this gorgeous condo with comfy king bed and fully equipped kitchen with full-size appliances and everything you need to cook and serve meals. Fast, free, reliable WiFi, and SmartTV to enjoy your favorite movies and shows. Heated pool and private sandy beach just steps away. Sunset Park next door is perfect for catching beautiful nightly sunsets. Centrally located to awesome Keys adventures just a few miles drive from the condo.

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!

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

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.

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.

Blue Palms Retreat
This 3 bedroom/2 bath oceanfront home with amazing views on Cudjoe Key private heated salt water swimming pool, shaded hang out area, ping pong table, corn hole game. The pier, gazebo, kayaks and kayak launch area is shared with one other home, Latitudes. You can dock your 24' boat at the pier. The water is shallow getting out to the channel with about a 2' draft.
Popular amenities for beachfront rentals in Cudjoe Key
Pet-friendly beachfront home rentals

Beach Home and Boater’s Paradise Sombrero

Powell Family Resort

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

Coco Plum Beach Paradise w Heated Pool & Boat Slip

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

Key West Luxury Houseboat at Yacht Club Resort

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

SeaEsta! Bring your boat & 1 block to the beach!
Beachfront home rentals with a pool

Wreckers House King Room - Adults Only

Oceanfront Sunrise Condo Private Beach Heated Pool

Stunning tropical Ocean view condo

(# 6)Waterfront Beautiful 4 Bed 3 Bath Pool Home

RV In The Keys | Tropical Retreat

Exquisite Luxury Oceanfront Complex Key Colony

Oceanfront Key West Condo

Marathon Oceanfront Suite | Balcony + 2 Luxe Baths
Private beachfront home rentals

Beachside Unit 22 - Private Beach on Atlantic

2 Bedroom Oceanfront Complex, Key Colony Beach

Key Lime Condo, Key Colony Beach Oceanfront & Pool

Modern Beachfront Steps to Beach/Pool, Key Colony

Sunny Beachfront Condo - Key Colony Beach & Pool

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

Ocean Oasis - Steps to Ocean and Pool Key Colony

Anchors Away Condo - Key Colony Beach Oceanfront
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 £164 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 & 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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- Sombrero Beach
- Smathers Beach
- Bahia Honda State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- The Turtle Hospital
- Key West Butterfly & Nature Conservatory
- Florida Keys Aquarium Encounters
- Fort Zachary Taylor Historic State Park
- Dolphin Research Center
- Boyd's Key West Campground
- Southernmost Point
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Curry Hammock State Park





