Cudjoe Key Holiday Rentals

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Holiday Rentals in Cudjoe Key

Private Secluded Ocean View & Pool Near Key West

Summerland Key
8.2 out of 10, Very good, (97)
"Enjoyed our stay. House was perfect for our family and guests. Great location."
United States
KELLIE T.
Private Secluded Ocean View & Pool Near Key West

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

Cudjoe Key
8.8 out of 10, Excellent, (73)
"Place was everything we needed, would definitely stay again "
United States
James h.
The price is AU$508
includes taxes & fees
21 Nov - 22 Nov
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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

Cudjoe Key
8.6 out of 10, Excellent, (150)
"An amazing place to come home to after a long day in the keys. Having a car is a must, but I would recommend time after time again and hope to come back again in the future"
United States
Travis W.
The price is AU$391
includes taxes & fees
15 Dec - 16 Dec
Cottage with Pool and Boat Dockage just minutes to Key West!

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

Cudjoe Key
9.0 out of 10, Wonderful, (159)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
Cottage with swimming pool and dockage, just minutes to Key West!

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key
9.0 out of 10, Wonderful, (88)
"Community is great, location in the Keys is great, house was perfect for our family of 3."
United States
Christina H.
Canal front, dockage, 2 bedroom, 2 bath

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

Cudjoe Key
8.8 out of 10, Excellent, (89)
"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."
United States
James P.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Wooden Bridge Resort and Marina

2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (271)
"We will definitely stay here again. Perfect spot to relax. Clean Rooms "
United States
Gregory
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
Stock Island
8.8 out of 10, Excellent, (168)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is AU$447
includes taxes & fees
19 Nov - 20 Nov
Aqua Lodges at Hurricane Hole Marina

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
Key West
8.2 out of 10, Very good, (820)
"Overall a good place to stay and value for money "
United States
Vijay Bhasker
Coconut Mallory Resort And Marina By Kees Vacations

Island View 1BR Residence With Balcony

2.0 star property
Key West
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
United States
Tonya
The price is AU$576
includes taxes & fees
1 Dec - 2 Dec
Island View 1BR Residence With Balcony

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

Key West
10.0 out of 10, Exceptional, (31)
" Comfortable"
United States
Total R.
The price is AU$763
includes taxes & fees
21 Nov - 22 Nov
The Salt Cay | Updated! Stunning Sunset View, Pool!

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Key West
8.6 out of 10, Excellent, (139)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is AU$590
includes taxes & fees
19 Nov - 20 Nov
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

New 4BR/4BA Sleeps 12+ minutes to Beach & Duval St. Private backyard pool oasis

2.0 star property
Beachside
New 4BR/4BA Sleeps 12+ minutes to Beach & Duval St. Private backyard pool oasis

Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis

Beachside
9.0 out of 10, Wonderful, (103)
"Everything was even better than in the pictures"
United States
john c.
The price is AU$997
includes taxes & fees
30 Nov - 1 Dec
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis

GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

Beachside
9.8 out of 10, Exceptional, (48)
"Wonderful view, lot's of space, great location "
United States
Valerie
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Stock Island
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is AU$784
includes taxes & fees
18 Nov - 19 Nov
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

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

Little Torch Key
9.6 out of 10, Exceptional, (85)
"Just a beautiful location, paradise. Spent mornings in the covered porch, husband loved the lagoon for fishing. We brought kayaks and the kids loved it. The dogs enjoyed the large property as well. "
United States
Kendra K.
The price is AU$1,079
includes taxes & fees
19 Nov - 20 Nov
Old Florida Style, wrap around porch, boat basin for dockage, open water

Party Like A Local in Key West, 2 bedroom 1 bath yacht at marina.

Stock Island
The price is AU$638
includes taxes & fees
18 Nov - 19 Nov
Party Like A Local in Key West, 2 bedroom 1 bath yacht at marina.

1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools

Stock Island
6.0 out of 10, (1)
" Host’s communication needs to improve! When we checked in, beddings didnt look fresh, so I asked: Me: sent pic & asked “this is how bed? Sheets washed/clean? Her reply: If we are going to have these kinds of problems because how I choose to make my bed then your more than welcome to try a room at the hotel ( copied & pasted from her text)"
United States
Myra
The price is AU$491
includes taxes & fees
18 Nov - 19 Nov
1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools

Living the Dream Key West Style

Stock Island
9.8 out of 10, Exceptional, (32)
"Everything was very nice. Staff was friendly and helpful ."
United States
Debra
The price is AU$529
includes taxes & fees
18 Nov - 19 Nov
Living the Dream Key West Style
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

Find out more about Cudjoe Key

Everything you need to know about Cudjoe Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cudjoe Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cudjoe Key holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cudjoe Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cudjoe Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cudjoe Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cudjoe Key holiday rentals we have selected for you start as low as AU$391 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cudjoe Key rentals

At Expedia, we put the best Cudjoe Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cudjoe Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cudjoe Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cudjoe Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.