Holiday Rentals in Cudjoe Key

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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, (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!

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

9.2 out of 10, Wonderful, (139)
"Loved it here! Caught lots of mangrove snappers on the dock we had an amazing time will be back again. Thank you"
The price is €314
includes taxes & fees
1 May - 2 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)
"Nice place could use some maintenence but great location & view"
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, (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!

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)
"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 €646
includes taxes & fees
28 Apr - 29 Apr
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)
"Good location and easy stay. "
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 €808
includes taxes & fees
9 May - 10 May
Atlantic View Luxury Villa with Pool

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (217)
"So good"
The price is €225
includes taxes & fees
28 Apr - 29 Apr
Old Wooden Bridge Resort and Marina

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 €254
includes taxes & fees
27 Apr - 28 Apr
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

9.2 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 €532
includes taxes & fees
7 May - 8 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)
"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 €251
includes taxes & fees
28 Apr - 29 Apr
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

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,

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 €341
includes taxes & fees
28 Apr - 29 Apr
Poolside Cottage #411

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!

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 €397
includes taxes & fees
28 Apr - 29 Apr
The Salt Cay | Updated! Stunning Sunset View, Pool!

Butterfly Nest | Newly Updated w/ Shared Pool

10.0 out of 10, Exceptional, (9)
"this place was perfect for us, it was away from the craziness but easy to get to where we wanted to be on a daily basses, The view of the pool off the deck was beautiful, just like the picture in your add, the sunrises were so beautiful!we loved it"
The price is €398
includes taxes & fees
29 Apr - 30 Apr
Butterfly Nest | Newly Updated w/ Shared Pool

Direct Ocean View from Your Condo-No Contact Check-In

9.4 out of 10, Exceptional, (152)
"I chose this property as it was ocean view, which it was. Easy access to the beach. Easy for deliveries and Uber pick ups. The only complaint was that the elevator was down due to a power surge the week before, but that was due to a storm and nothing could help that. We had to go up and down 4 flights of stairs, not a big deal for my sister and I, but difficult for our 73 year old mother. The property manager was great - quick responses to questions/concerns. If you have someone that...
Direct Ocean View from Your Condo-No Contact Check-In
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, (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

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 €308
includes taxes & fees
11 May - 12 May
Margaritaville Beach House Key West

Fairfield Inn and Suites by Marriott Key West

3.0 star property
7.8 out of 10, Good, (1093)
"I was very excited about visiting this property and hanging out by the pool. However, we weren’t impressed with the friendliness of the staff who drove the shuttle and the pool bartender who closed the bar early with my husband standing there ready to order drinks during Spring Break week. The housekeeping staff were an exception and were great. The room was clean and the towels were nice. The double beds were small for us to fit comfortably on. Overall a decent hotel but friendly staff would...
The price is €194
includes taxes & fees
27 May - 28 May
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.