Holiday Rentals in Cudjoe Key

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Cudjoe Key holiday rentals

Cottage with swimming pool and 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, (160)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
The price is €305
includes taxes & fees
27 Dec - 28 Dec
Cottage with swimming pool and dockage, just minutes to Key West!

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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (75)
"It was ok for what we needed. Needs some repairs though."
United States
Craig M.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West
Summerland Key
8.2 out of 10, Very good, (98)
"Thank you so much for the great stay! The ocean view was beautiful! The landscaping with surrounding trees and flowers was lovely! The house was comfortable and had everything that we needed. It was perfect for our family!"
United States
Deidra B.
Private Secluded Ocean View & Pool Near Key West

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is €297
includes taxes & fees
21 Dec - 22 Dec
Aqua Lodges at Hurricane Hole Marina

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (278)
"We loved it here. So beautiful and quiet."
United Kingdom
Mark
Old Wooden Bridge Resort and Marina

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
Ocean Front One Bedroom Residence

Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (2)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is €483
includes taxes & fees
19 Dec - 20 Dec
Island View 1BR Residence With Balcony

Ocean Front 1BR Suite With Direct Beach Access

Ocean Front 1BR Suite With Direct Beach Access
2.0 star property
Key West
10.0 out of 10, Exceptional, (2)
"Clean and spacious. Great view from room!"
United States
Jacqueline
The price is €594
includes taxes & fees
19 Dec - 20 Dec
Ocean Front 1BR Suite With Direct Beach Access

Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations
3.0 star property
Key West
8.2 out of 10, Very good, (821)
"The staff goes above and beyond very, very warm and nice people"
United States
erik
Coconut Mallory Resort And Marina By Kees Vacations

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

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 €437
includes taxes & fees
20 Dec - 21 Dec
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Charming 3-bedroom houseboat with AC in perfect Key West, Sleeps 10 Guests!

Charming 3-bedroom houseboat with AC in perfect Key West, Sleeps 10 Guests!
2.0 star property
Stock Island
Charming 3-bedroom houseboat with AC in perfect Key West, Sleeps 10 Guests!

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

Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Key West
8.6 out of 10, Excellent, (140)
"Clean, easy check-in, great pools, quiet area, comfy beds. Will book again!"
Germany
Julia P.
The price is €376
includes taxes & fees
21 Dec - 22 Dec
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.0 out of 10, Wonderful, (31)
"Great place, great location, great communication from host!"
United States
Lara P.
The price is €501
includes taxes & fees
19 Dec - 20 Dec
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
9.8 out of 10, Exceptional, (36)
"Everything was very nice. Staff was friendly and helpful ."
United States
Debra
The price is €416
includes taxes & fees
19 Dec - 20 Dec
Living the Dream Key West Style

Super-Cozy boat in Key West!

Super-Cozy boat in Key West!
Key West
8.0 out of 10, Very good, (1)
"Yes, Troy was very welcoming. Met me at the airport and gave me a ride to his boat. Very accomodating. 2 diff.options for sleeping and boat was very comfortable. Plenty of fresh towels.Picked up whatever I needed and brought it out to me. Thx!"
United States
rachael K.
The price is €274
includes taxes & fees
19 Dec - 20 Dec
Super-Cozy boat in Key West!

**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...

**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...
Beachside
9.8 out of 10, Exceptional, (108)
"the condo was great roomingnice locationbeautiful, fun, great memories were made"
United States
heidi t.
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...

The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1)
The price is €603
includes taxes & fees
20 Dec - 21 Dec
The Grenada Suite Pool View Private Balcony

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

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!

Two Bedroom Residence With Balcony

Two Bedroom Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1)
"The roosters crowing early morning was irritating "
United States
Catherine
The price is €697
includes taxes & fees
19 Dec - 20 Dec
Two Bedroom Residence With Balcony

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

Old Florida Style, wrap around porch, boat basin for dockage, open water
Little Torch Key
9.6 out of 10, Exceptional, (88)
"This place really had it all , one of my best stays yet anywhere. "
United States
Charles M.
The price is €765
includes taxes & fees
1 Jan - 2 Jan 2026
Old Florida Style, wrap around porch, boat basin for dockage, open water
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.
Save an average of 15% on thousands of hotels when you're signed in

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, apart-hotels, 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 favorite 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 depends 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 €274 per night. Entering your travel dates in the search wizard you might find 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.