Cudjoe Key Holiday Rentals

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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, (135)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
Cottage with Pool and Boat Dockage just minutes to Key West!

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

9.0 out of 10, Wonderful, (145)
"We had a wonderful stay in a small cottage in Cudjoe Key. It was a fun little place stay. Location was great for visiting the other Keys. I would seriously look at staying in one of the bigger cottages if I brought my family down. Thank you very much!"
The price is NZ$480
includes taxes & fees
30 May - 31 May
Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (140)
"We had a wonderful time at your place. Thank you for having us, we loved the Keys!"
The price is NZ$588
includes taxes & fees
5 May - 6 May
Cottage with Pool and Dockage, just minutes to Key West

Oasis - Ocean view with pool and hot tub

9.0 out of 10, Wonderful, (26)
"To have my family under one roof for one week is amazing! The house was spacious, the outdoor decks, pool, kayaks, dock, and large kitchen/living room/dining space was perfect! "
Oasis - Ocean view with pool and hot tub

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

8.4 out of 10, Very good, (108)
"The whole experience was decent until the last night. We met with a lot of termites and two cockroaches"
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

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

10.0 out of 10, Exceptional, (1)
"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!

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (230)
"Everything was very nice. We enjoyed sitting down by the water any time. It was close to everything we were interested in seeing and doing. Great stay."
The price is NZ$1,207
includes taxes & fees
4 May - 5 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

Ocean/Canal Views 21ft Dock - Venture Out #357

8.2 out of 10, Very good, (20)
"My wife and I enjoyed the view down the channel to the open water, especially during sunrise. This is a good central location for some great restaurants and activities."
Ocean/Canal Views 21ft Dock - Venture Out #357

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 NZ$1,550
includes taxes & fees
19 May - 20 May
Atlantic View Luxury Villa with Pool

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (223)
"Lovely, quiet place on the water with plenty of space in the houseboat"
The price is NZ$432
includes taxes & fees
8 May - 9 May
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (134)
"Would definitely stay here again! "
The price is NZ$553
includes taxes & fees
14 May - 15 May
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, (808)
"Very tropical, on the water. Everything u need in amenities. Pools were great!"
Coconut Mallory Resort And Marina By Kees Vacations

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

9.6 out of 10, Exceptional, (7)
"Kevin and Capt. Phil were great hosts. Would definitely stay there again. "
The price is NZ$982
includes taxes & fees
12 May - 13 May
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

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

10.0 out of 10, Exceptional, (6)
"My wife and I have been to Key West many times, and Liam's house boat has to be the coolest place we've stayed yet! "
The price is NZ$461
includes taxes & fees
27 May - 28 May
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (174)
"Very comfortable and clean place right by water, had a great stay "
Direct Oceanfront Cottage-Sunrise View- #2,

Poolside Cottage #411

10.0 out of 10, Exceptional, (42)
"Lovely home to stay in for a couple of nights on Key West"
The price is NZ$624
includes taxes & fees
14 May - 15 May
Poolside Cottage #411

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

9.8 out of 10, Exceptional, (286)
"Great time!! Great place!!"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym

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

10.0 out of 10, Exceptional, (12)
"We loved our condo. Perfect location for spring break with our kids and grandchild. Very clean. Would stay here again. Pool day was great! "
The price is NZ$964
includes taxes & fees
12 May - 13 May
The Salt Cay | Updated! Stunning Sunset View, Pool!

Sunshine Key RV Resort & Marina

2.0 star property
8.8 out of 10, Excellent, (146)
"I enjoyed staying in a tiny house. The property was amazing!"
Sunshine Key RV Resort & Marina

Butterfly Nest | Newly Updated w/ Shared Pool

10.0 out of 10, Exceptional, (12)
The price is NZ$963
includes taxes & fees
6 May - 7 May
Butterfly Nest | Newly Updated 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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Other types of properties in Cudjoe Key you may be interested in

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

8.6 out of 10, Excellent, (135)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
Cottage with Pool and Boat Dockage just minutes to Key West!

Margaritaville Beach House Key West

4.0 star property
8.6 out of 10, Excellent, (1710)
"We’ve stayed here multiple times always a great trip "
The price is NZ$562
includes taxes & fees
18 May - 19 May
Margaritaville Beach House Key West

Fairfield Inn and Suites by Marriott Key West

3.0 star property
7.8 out of 10, Good, (1100)
"Staff is professional and pool is very nice."
The price is NZ$394
includes taxes & fees
1 June - 2 June
Fairfield Inn and Suites by Marriott Key West
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.

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.