Holiday Rentals in Cudjoe Key

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Holiday Rentals in Cudjoe Key

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (144)
"We had a nice stay at the cottages. Location worked well for our fishing excursions and access across the street to old RT 1 to walk the dogs. "
Cottage with Pool and Boat Dockage just minutes to Key West!

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.8 out of 10, Excellent, (72)
"Very nice quiet place for your lower key vacation. Nice accommodations and easy drive to Key West and Islamorada and several state parks. "
The price is €326
includes taxes & fees
4 Aug - 5 Aug
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Private Secluded Ocean View & Pool Near Key West

8.2 out of 10, Very good, (93)
"Everything was exactly as described, the host was gracious and communicative, the house is great for a large group and a quiet location"
Private Secluded Ocean View & Pool Near Key West

Cottage with swimming pool and dockage, just minutes to Key West!

9.0 out of 10, Wonderful, (153)
"Wonderful stay with great property and pool. Very well maintained!"
Cottage with swimming pool and dockage, just minutes to Key West!

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

8.4 out of 10, Very good, (114)
"Deer in the front yard, perfect location, clean and friendly "
The price is €477
includes taxes & fees
4 Aug - 5 Aug
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (236)
"My family of older boys enjoyed a great stay at the location. The property is well maintained. They have some very nice amenities and it was conveniently located to explore the lower keys. "
The price is €718
includes taxes & fees
9 Aug - 10 Aug
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

10.0 out of 10, Exceptional, (3)
"The place was just as pictured, very comfortable and private. Very clean and spacious. The only issue we had was trying to get the back door to lock. "
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

Atlantic View Luxury Villa with Pool

3.5 star property
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
The price is €880
includes taxes & fees
16 Aug - 17 Aug
Atlantic View Luxury Villa with Pool

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (254)
"I love ❤️ this place "
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (160)
"The stay was beautiful "
The price is €205
includes taxes & fees
11 Aug - 12 Aug
Aqua Lodges at Hurricane Hole Marina

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (818)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (77)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
The price is €618
includes taxes & fees
18 Aug - 19 Aug
Old Florida Style, wrap around porch, boat basin for dockage, open water

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

7.4 out of 10, Good, (10)
"We were here celebrating 55th birthdays and had a blast. Great location and communication with Capt. We will return for sure, hoping to make it an annual get together."
The price is €655
includes taxes & fees
11 Aug - 12 Aug
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

9.8 out of 10, Exceptional, (295)
"Excellent accommodations, gorgeous condon"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

The Salt Cay | Updated! Stunning Sunset View, Pool!

9.8 out of 10, Exceptional, (20)
"Place was so clean and perfect location! Very quiet and relaxing"
The price is €328
includes taxes & fees
17 Aug - 18 Aug
The Salt Cay | Updated! Stunning Sunset View, Pool!

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

10.0 out of 10, Exceptional, (7)
"The ideal getaway, I brought a grill and a pan and did all the cooking outside on the deck. Took paddle boards through mangrove tunnels and saw tons of fish. Had a baby sea turtle swim up to the boat. "
The price is €239
includes taxes & fees
14 Aug - 15 Aug
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (186)
"Quiet area, ocean view, roomy place for family of 3. Will stay again, thank you! "
Direct Oceanfront Cottage-Sunrise View- #2,

Cat Island Suite | Beautifully Renovated w/ Pool!

10.0 out of 10, Exceptional, (21)
"Great location. Enjoyed our stay!!"
The price is €318
includes taxes & fees
10 Aug - 11 Aug
Cat Island Suite | Beautifully Renovated w/ Pool!

Oceanfront 4-Bed 3-Bath home with pool

9.4 out of 10, Exceptional, (73)
"It was a great location in the back, not on the main road. Very quiet, great view, and good place for kids if you are traveling with kids. Used golf carts and was able to get everywhere in 5-10 mins. Overall great vacation and awesome location to stay. "
Oceanfront 4-Bed 3-Bath home with pool

The Andros | Incredible Views w/ Shared Pool

8.6 out of 10, Excellent, (21)
"The short stay we had at your property was absolutely amazing. It is going to be very difficult to top. I can't imagine visiting any other property if I were to come back."
The price is €328
includes taxes & fees
17 Aug - 18 Aug
The Andros | Incredible Views w/ Shared Pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cudjoe Key Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Cudjoe Key?

Yes, there are holiday rentals close to the most popular sights in Cudjoe Key, or you can select a more secluded option if you're looking for a relaxing stay. Cudjoe Key is known for its seafood restaurants and seaside.

What are some of the best holiday rentals that Cudjoe Key has to offer?

3 night minimum! Spectacular Ocean Views!: This highly rated holiday home rental in Cudjoe Key offers a balcony, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Our travellers also rate Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West as a favourite home for rent in Cudjoe Key.

How many holiday rentals are there in Cudjoe Key?

With 205 Expedia holiday rentals, you're guaranteed to find just the right place for your Cudjoe Key stay.

What can I see and do in Cudjoe Key?

While exploring the area, visit family-friendly sights like Key West Visitors Center, or get outside and enjoy nature at Florida Keys Beaches. Boca Chica Beach and Calusa Beach are a couple of places you'll find in the wider area.

What are holiday rentals like in Cudjoe Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cudjoe Key. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips or small group gatherings.