Cudjoe Key Holiday Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
25 Apr - 26 Apr
Tomorrow
26 Apr - 27 Apr
This weekend
25 Apr - 27 Apr
Next weekend
2 May - 4 May

Holiday Rentals in Cudjoe Key

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

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

8.6 out of 10, Excellent, (134)
"2nd time and it's a nice relaxing stay.Catch a few fish off the dock or to one of the bridges.And my dogs love it!!"
Cottage with Pool and Boat Dockage just minutes to Key West!
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Fridge, microwave, oven, stovetop

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

8.8 out of 10, Excellent, (145)
"We have stayed in the Keys often. This place has it all…great water views, kitchen of glass with more great views and an open floor plan full of light. The house is clean and nicely decorated. Dock was perfect for the boat we rented…caught lots of lobster the last several days of the season!"
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cottage with swimming pool and dockage, just minutes to Key West!
Miscellaneous

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

9.0 out of 10, Wonderful, (145)
"We have been staying at this property for over 20 years. It’s the perfect location for visiting all of the lower keys. "
Cottage with swimming pool and dockage, just minutes to Key West!
Cottage with Pool and Dockage, just minutes to Key West
Pool

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (138)
"This was a good property was exactly what was advertised"
The price is HK$1,358
HK$2,703 total
includes taxes & fees
1 May - 2 May
Cottage with Pool and Dockage, just minutes to Key West
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
A heated pool

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

9.8 out of 10, Exceptional, (217)
"The property and all of the amenities were absolutely amazing! Hosts Rick and Laura were very kind and made sure we enjoyed our stay. This was my first trip to the keys and I will definitely book again with them!"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Balcony

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

8.4 out of 10, Very good, (107)
"Definitely need to update the property. Day to day cleanliness was good but many burnt out light bulbs or mismatched bulbs. A coat of paint and updated furniture would help. House A has no view of the water and may have chosen a different place in the complex if i had known. Pool was well taken care of and lots of privacy by the home. Convenient to Key west and lots of good local restaurant choices. Beds were very comfortable. "
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Fridge, microwave, oven, stovetop

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

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
On the beach, sun-loungers, beach towels

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

9.8 out of 10, Exceptional, (230)
"We had the best time at this property! It was clean and very nice. We loved how the girls could swim in the pool and the boys could be fishing at the dock and you can see everyone. Lots of fun stuff to catch out front. We had the best time!"
The price is HK$2,134
HK$5,560 total
includes taxes & fees
29 Apr - 30 Apr
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Ocean/Canal Views 21ft Dock - Venture Out #357
Terrace/patio

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

8.2 out of 10, Very good, (20)
"Good location and easy stay. "
Ocean/Canal Views 21ft Dock - Venture Out #357
Atlantic View Luxury Villa with Pool
Swim-up bar

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 HK$3,928
HK$7,134 total
includes taxes & fees
9 May - 10 May
Atlantic View Luxury Villa with Pool
Old Wooden Bridge Resort and Marina
Living area

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (217)
"So good"
The price is HK$1,078
HK$1,989 total
includes taxes & fees
28 Apr - 29 Apr
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
Private kitchen

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (131)
"Really enjoyed the stay. All our “neighbors” were respectful of each other The boat house was clean The manatees stole the show!"
The price is HK$756
HK$2,152 total
includes taxes & fees
27 Apr - 28 Apr
Aqua Lodges at Hurricane Hole Marina
Coconut Mallory Resort And Marina By Kees Vacations
Meeting facility

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
Terrace/patio

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

9.2 out of 10, Wonderful, (5)
"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 HK$1,164
HK$4,578 total
includes taxes & fees
7 May - 8 May
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Direct Oceanfront Cottage-Sunrise View- #2,
On the beach

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (173)
"My husband and I enjoyed the peacefulness of the area, the beautiful view, the prime location for great places to eat and things to do, the short drive to Key West and Bahia Honda. The cottage was clean, the bed comfy and all was as described. Susan was quick in responding to any questions we had. We will stay here again, I’m sure. "
Direct Oceanfront Cottage-Sunrise View- #2,
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
1 bedroom, Internet, bed sheets

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

10.0 out of 10, Exceptional, (6)
"This was a perfectly unique and special experience. Matt was amazing to work with for arrival and departure. Timely and exactly as Liam said everything would be. They put special touches on the stay, ice bucket, two waters, beach towels, our name on a cute sign, a cooler, extra covers and everything you need for a Glamping stay on the water! Camping at its best! We definitely plan to come back and will recommend this stay to our friends. This is perfect for outdoor lovers and adventurous people...
The price is HK$1,311
HK$2,160 total
includes taxes & fees
29 Apr - 30 Apr
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Poolside Cottage #411
Outdoor pool

Poolside Cottage #411

10.0 out of 10, Exceptional, (41)
"Lovely home to stay in for a couple of nights on Key West"
The price is HK$1,738
HK$2,928 total
includes taxes & fees
27 Apr - 28 Apr
Poolside Cottage #411
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (286)
"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!
A heated pool

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

10.0 out of 10, Exceptional, (11)
"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 HK$1,292
HK$3,641 total
includes taxes & fees
27 Apr - 28 Apr
The Salt Cay | Updated! Stunning Sunset View, Pool!
Sunshine Key RV Resort & Marina
Kayaking

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
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.
Don't see what you're looking for?
See all available properties in Cudjoe Key
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Cudjoe Key you may be interested in

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

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

8.6 out of 10, Excellent, (134)
"2nd time and it's a nice relaxing stay.Catch a few fish off the dock or to one of the bridges.And my dogs love it!!"
Cottage with Pool and Boat Dockage just minutes to Key West!
Margaritaville Beach House Key West
Outdoor pool

Margaritaville Beach House Key West

4.0 star property
8.6 out of 10, Excellent, (1704)
"Everything was wonderful, I would stay here again. The room was beautiful. The grounds were small but had a safe and comfy vibe. "
The price is HK$1,978
HK$2,719 total
includes taxes & fees
11 May - 12 May
Margaritaville Beach House Key West
Beachside Resort & Residences
Outdoor pool, pool umbrellas, pool loungers

Beachside Resort & Residences

3.5 star property
8.4 out of 10, Very good, (1010)
"Great place. A little dated, but after all a great stay for a business trip. "
The price is HK$1,513
HK$2,095 total
includes taxes & fees
29 Apr - 30 Apr
Beachside Resort & Residences
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.