
Beachfront vacation rentals in Cudjoe Key
Find and book unique beachfront homes on Airbnb
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 €172 per night before taxes and fees

Verified guest reviews
Over 530 verified reviews to help you choose

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!
Top-rated beachfront rentals in Cudjoe Key
Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

ATLANTIS...Ocean Front Cottage Retreat!
ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

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.

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.

Beachside Unit 33-Private Tropical Beach Plus Pool
Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests (0-2 years old count as a guest). 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.”

Waterfront Villa & Sunset Views
Come and relax on your own veranda that overlooks the turquoise waters of the beautiful Duck Key. The outdoor living space is quiet and serene, making it a perfect place to unwind. Families and honeymooners alike can enjoy this island oasis. Centrally located at Mile Marker 61, Duck Key is just a short drive to Key West. Explore everything the Florida Keys have to offer or stay local to enjoy world-renowned restaurants, fishing, snorkeling, and diving. The opportunities are endless.

Beautiful Beachfront Home 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.

Vibrant Beachfront Villa
Welcome to Beachfront Villa that has recently been renovated. The 2 bedroom 1.5 bath luxury villa is located in the popular area of Duck key alongside of Hawks Cay Resort. Duck Key marina is located across the street where you can dock your boat or charter a boat for the day. Enjoy stunning sunset views from the back porch. Kitchen includes all amenities including silverware ,plates , cups , and pots. Linens and towels provided. *** Pets welcome with host approval and pet fee. ****

Ocean Oasis!OceanView-Private Beach/Pool/TikiHuts
Welcome to Ocean Oasis, your tropical haven in Marathon, Florida! Our stunning 2-bedroom, 2-bathroom condo is located at 501 E Ocean Dr, Marathon, FL 33050. Ocean Oasis offers the ultimate beachfront retreat, with a King-sized bed in the master bedroom and two full-sized beds in the second bedroom, comfortably sleeping six. The spacious balcony boasts breathtaking views of the ocean and pool, perfect for sipping morning coffee or enjoying a sunset cocktail. No Pets Allowed.

Standard Suite at Sugarloaf Key Hotel
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 4-person 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!

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.

The Guest House - Sugarloaf Beach 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. A truly one-of-a-kind beachfront retreat offering a private sandy beach and dock with boat dockage. This tropical escape delivers a relaxed, family-friendly atmosphere that makes you feel as if you’re on your own private island in the Florida Keys. .
Popular amenities for Cudjoe Key beachfront rentals
Beachfront home rentals with a pool

Private Beach in Marathons Key Colony Beach

Cabana Club Condo: Key Colony Beach, FL

Ocean front 1BR/1BA Suite w/ kitchen & living rm

Paradise found! Sea-Esta Condo beach and pool.

Canal/Dock - Cabana Club - Pickleball - Remodeled

Seaside Villa~ Charming Beachfront Condo w/ Pool!

Oceanfront oasis beach views heated pool U34

Beach House 5BR/5BA, 1/2 mile to Sombrero Beach, P
Pet-friendly beachfront home rentals

SeaEsta! Bring your boat & 1 block to the beach!

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

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

Boaters delight! 1 min to open water, Dock & Beach

Beach Home and Boater’s Paradise Sombrero

Walk to Beach, 90' Dock, Huge Pool, Kayaks

Coco Plum Beach Paradise w Heated Pool & Boat Slip

Calypso Cottage
Private beachfront home rentals

Villa 5028 on Duck Key BOAT SLIP available

Spectacular 2BR Oceanfront Dog Friendly | Dock

A Suite Escape

Paradise awaits.

Sandy Beach Just Steps Away

Coastal Key Colony Beach Condo, Oceanfront Complex

Oceanfront Sunrise Condo Private Beach Heated Pool

Sunrise View Condo - Key Colony - Private Beach
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- Beachfront rentals Monroe County
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- Sombrero Beach
- Smathers Beach
- Bahia Honda State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
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- Southernmost Point
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- Dolphin Research Center
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