
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.

*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.

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.

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!

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.

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.

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 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.
Popular amenities for Cudjoe Key beachfront rentals
Pet-friendly beachfront home rentals

Powell Family Resort

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

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

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

Charming Beach House directly ON the beach

LARGE LOT & RV | Fishermen Camp

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

Ocean front with private beach and pool!

Port Antigua NEW lux apart

Oceanfront Key West Condo

Beachfront Condo on Coco Plum Beach w/heated pool

Luxury Retreat in the Keys | Boat Dock | Beach

Grassy Key Ocean Front Beach House
Private beachfront home rentals

Beachside Unit 36 Private Patio & Beach Plus Pool

Beachside Unit 22 - Private Beach on Atlantic

Oceanfront Breeze, Stunning Views, Beach/Pool

Key Colony Beach Luxury Condo, New Modern Interior

Keys Breeze Ocean View Condo & Pool - Key Colony

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

Anchors Away Condo - Key Colony Beach Oceanfront

Beachside Unit 27 - The Beach is Calling You!
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 $210 per night before taxes and fees 
 - Verified guest reviews- Over 600 verified reviews to help you choose 
 - Family-friendly vacation rentals- 10 properties offer extra space & kid-friendly amenities 
 - Vacation rentals with a pool- 10 properties feature pools 
 - Wi-Fi availability- 10 of Cudjoe Key vacation 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! 
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