
Holiday rentals with beach access in Cudjoe Key
Find and book unique rentals with beach access on Airbnb
Quick stats about holiday rentals with beach access in Cudjoe Key

Total holiday rentals
Explore 50 holiday rentals in Cudjoe Key

Nightly prices starting at
Cudjoe Key holiday rentals start at $103 SGD per night before taxes and fees

Verified guest reviews
Over 1,880 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
50 of Cudjoe Key holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Cudjoe Key rentals

4.8 Average rating
Cudjoe Key stays are highly rated by guests – averaging 4.8 out of 5!
Top-rated rentals with beach access in Cudjoe Key
Guests agree: these rentals with beach access are highly rated for location, cleanliness and more.

Beautiful Cottage & Amenities in Gated Community
Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

Captain’s Quarters Ahoy Mateys! Florida, Keys
This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

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.

The Guest House - Sugarloaf Beach Key West
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. Enjoy sweeping ocean views and direct access to a natural private beach—ideal for kayaking, paddleboarding, or simply unwinding beneath the swaying palm trees with a book in hand. Perfect for guests seeking both adventure and total relaxation.

Waterfront Sanctuary in the Keys!
Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

Waterfront Duck Key Villa - Sleeps 8 (7058)
BEST VIEW IN DUCK KEY!!!! Waterfront Villa at the heart of the Florida Keys - Duck Key Florida. Beautiful location with easy access to both the Atlantic Ocean and the Gulf of Mexico. Come check us out and see for yourself what the exclusive Duck Key area has to offer. DOCK INCLUDED-35 Foot. Conveniently behind the village! The Village at Hawks Cay Villas by KeysCaribbean are not affiliated with the Hawks Cay Resort; our guests do not have access to hotel amenities.

b watervibe
Disfruta de los sonidos de la naturaleza cuando te quedes en este lugar único. Es algo diferente para disfrutar con tu pareja de un momento romántico y divertido y así relajarse y olvidarse de la vida cotidiana. Puedes disfrutar de la pesca ,de paseos en kayak ,vivir una aventura y disfrutar de otras actividades locales.Prueba de la expericiensa y ya ustedes diran.Esta casa flotante ofrece un espacio para 2 adultos. Está Esta es una experiencia de Acampada .

Private Pool Tropical Oasis - Centrally Located
Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

Paradise in Key Colony Beach + Cabana Club
Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

Florida Keys Resort-Style Home w/ Pool & Dock 5/3
Perfect for families, couples, groups, or solo travelers, this spacious home offers 5 bedrooms, 3 bathrooms, an open living room, and a fully stocked kitchen. Easy to reach and simple to access, it’s set in a peaceful neighborhood close to island fun and water adventures. Just a short walk to Sweet Savannah’s Ice Cream & Sweets Parlor, this retreat is ideal for relaxing or exploring. We look forward to hosting you!

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 rentals with beach access in Cudjoe Key
Apartment rentals with beach access

Key West Beachside 1400sf, 2 Bedroom Condo

Quiet Canalfront Retreat • Near Sombrero Beach

Key West Beach House

Beachside Unit 22 - Private Beach on Atlantic

Duval Balcony - Street Suite

Waterfront Escape | Pool, Tiki, Breakfast & Marina

Marathon Studio on Lovely Gulf Front Resort

Rare Beach Front Resort Key West- 2BD/2BA
House rentals with beach access

KCB Tropical Escape

Oceanfront Rooftop Views w/ 75ft of Dockage

Heated&Cooled PrivatePool/CabanaClub/Bikes/PaddleB

4BR 3B, Heated Pool & Spa, 60' Dock

Oceanfront mermaid house pool and dock

Waterfront Oasis3/2 Direct Ocean

Beach House, Private Pool, Dock, Gulf View Sunsets

Casa Blue Flamingo
Apartment rentals with beach access

Ocean Front Studio private Sandy Beach in Key West

Villa 5087 on Duck Key BOAT SLIP available

Keys Breeze Ocean View Condo & Pool - Key Colony

Affordable Beachfront Luxury Condo Sleeps 6

Fully renovated 2/2 bath condo w/ shared pool!

Paradise found! Sea-Esta Condo beach and pool.

Henry's Piece of Paradise On The Ocean In Key West

P41 - Beach Front condo with 2 bedrooms, 2 bath, p
When is the best time to visit Cudjoe Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $408 SGD | $447 SGD | $510 SGD | $401 SGD | $381 SGD | $333 SGD | $379 SGD | $347 SGD | $293 SGD | $342 SGD | $362 SGD | $439 SGD |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°C |
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- Rentals with beach access Monroe County
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- Rentals with beach access United States
- Sombrero Beach
- Smathers Beach
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Bahia Honda State Park
- Fort Zachary Taylor Historic State Park
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Conch Key
- Dolphin Research Center
- Key West Butterfly & Nature Conservatory
- Southernmost Point
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Curry Hammock State Park
- Key West Aquarium





