Cudjoe Key Holiday Rentals

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Check prices for these dates

Tonight
18 Apr - 19 Apr
Tomorrow
19 Apr - 20 Apr
This weekend
18 Apr - 20 Apr
Next weekend
25 Apr - 27 Apr

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, (133)
"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!
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!"
The price is HK$2,329
HK$4,863 total
includes taxes & fees
25 Apr - 26 Apr
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, (143)
"We had a nice time at our stay. We stayed for 3 nights and it was close to key west and the docks were nice to fish off of. Place was clean and everything worked fine for us. "
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, (136)
"Very nice"
The price is HK$1,358
HK$2,712 total
includes taxes & fees
1 May - 2 May
Cottage with Pool and Dockage, just minutes to Key West
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Outdoor pool

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

8.8 out of 10, Excellent, (153)
"As always, we had a great time. Nothing fancy but just a quiet get-away. "
The price is HK$1,281
HK$2,313 total
includes taxes & fees
19 Apr - 20 Apr
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Outdoor dining

Cudjoe Cottages, swimming pool, just 20 miles from Key West

8.8 out of 10, Excellent, (137)
"Nice location. Comfortable place although the couch and living room chair were old and stained. "
The price is HK$2,135
HK$4,676 total
includes taxes & fees
25 Apr - 26 Apr
Cudjoe Cottages, swimming pool, just 20 miles from 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, (215)
"My mom and I were absolutely amazed by the property, we loved everything and hope to come back again!"
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!
Shower, hair dryer, towels

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, (229)
"My family and I (two adults, two teens) fully enjoyed our trip. This was one of the cleanest rental properties I’ve ever stayed in! We loved having bikes and kayaks available, plus a pool and dock. The night stars were gorgeous and the daytime water views were lovely. Great spot in the lower Keys for access to marinas and the Key Deer Refuge while being quiet enough to fully check out. "
The price is HK$2,135
HK$5,563 total
includes taxes & fees
19 Apr - 20 Apr
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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$3,930
HK$7,138 total
includes taxes & fees
4 May - 5 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, (216)
"Unique lodging experience. The houseboat was clean and comfortable. Would definitely stay again."
The price is HK$1,079
HK$1,990 total
includes taxes & fees
21 Apr - 22 Apr
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (128)
"It was a great experience being on a houseboat."
The price is HK$757
HK$2,153 total
includes taxes & fees
27 Apr - 28 Apr
Aqua Lodges at Hurricane Hole Marina
Coconut Mallory Resort And Marina By Kees Vacations
2 outdoor pools

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

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$1,312
HK$2,161 total
includes taxes & fees
29 Apr - 30 Apr
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Miscellaneous

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

9.2 out of 10, Wonderful, (5)
"Was just a teaser initial trip to Key West but staying on the water was awesome! Beautiful views and great amenities. Kevin and Captain Philip were great throughout the whole process including great local recommendations! One thing to note, if you are 6’ plus, will need to watch your head and the steps downstairs require concentration. As a shorter person (barely 5’!) it all worked perfectly for me! Look forward to staying again and taking the boat out next time! "
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, (174)
"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. "
The price is HK$1,747
HK$3,203 total
includes taxes & fees
21 Apr - 22 Apr
Direct Oceanfront Cottage-Sunrise View- #2,
Poolside Cottage #411
Outdoor dining

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$1,739
HK$2,929 total
includes taxes & fees
27 Apr - 28 Apr
Poolside Cottage #411
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$1,432
HK$3,760 total
includes taxes & fees
23 Apr - 24 Apr
The Salt Cay | Updated! Stunning Sunset View, Pool!
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, (285)
"wonderful property and very convenient to everything on the island"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
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!
Exterior

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

8.6 out of 10, Excellent, (133)
"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!
Beachside Resort & Residences
Outdoor pool, pool umbrellas, pool loungers

Beachside Resort & Residences

3.5 star property
8.4 out of 10, Very good, (1011)
"Perfect place to stay în Key West, nice pool and beach area "
The price is HK$1,586
HK$2,177 total
includes taxes & fees
6 May - 7 May
Beachside Resort & Residences
Margaritaville Beach House Key West
Beach nearby, white sand

Margaritaville Beach House Key West

4.0 star property
8.6 out of 10, Excellent, (1724)
"Very nice place to stay. I didnt particularly like getting hit with unexpected resort fees at the end of my trip though."
The price is HK$2,236
HK$3,012 total
includes taxes & fees
5 May - 6 May
Margaritaville Beach House 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.