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, (143)
"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!

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

8.4 out of 10, Very good, (114)
"Great place to get away. House and property were nice. If your bring a boat, you have to watch the tides. Flats or a smaller bay boat will be fine. Had a 21 foot center console. Low tide you just have to take it slow out to the channel. Great options for docking your boat. A lot of space for boat trailers. Location of property is nicely situated. "
The price is €477
includes taxes & fees
2 Aug - 3 Aug
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Endless Summer Hideaway - lot 181

The price is €264
includes taxes & fees
14 Aug - 15 Aug
Endless Summer Hideaway - lot 181

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

9.8 out of 10, Exceptional, (226)
"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

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

9.8 out of 10, Exceptional, (235)
"We (family of 5) really enjoyed our stay. All the equipment was as listed and in great condition. The location was perfect if you're looking for a less hectic Florida Keys experience."
The price is €773
includes taxes & fees
25 Jul - 26 Jul
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (247)
"Old Wooden Bridge was one of the coolest and most relaxing spots my family and I have ever stayed at! House Boat was clean and wonderful view of the beautiful waters in Big Pine Key! Also we were greeted by Key Deer every night which was an Amazing experience! "
Old Wooden Bridge Resort and Marina

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (158)
"Such a unique stay and affordable!"
The price is €195
includes taxes & fees
25 Jul - 26 Jul
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, (817)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

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

9.6 out of 10, Exceptional, (76)
"Very nice place to stay. Quick and efficient communication with host! Seemless check in and check out process. "
Old Florida Style, wrap around porch, boat basin for dockage, open water

Living the Dream Key West Style

10.0 out of 10, Exceptional, (19)
"Wonderful spot, great hosts. Spectacular sunset cruise aboard Serenity. "
The price is €302
includes taxes & fees
17 Jul - 18 Jul
Living the Dream Key West Style

ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!

9.8 out of 10, Exceptional, (207)
"great property"
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!

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

8.0 out of 10, Very good, (9)
"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 €446
includes taxes & fees
1 Aug - 2 Aug
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

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

10.0 out of 10, Exceptional, (18)
"We had a wonderful stay and would definitely recommend this property! "
The price is €321
includes taxes & fees
5 Aug - 6 Aug
The Salt Cay | Updated! Stunning Sunset View, Pool!

Cat Island Suite | Beautifully Renovated w/ Pool!

10.0 out of 10, Exceptional, (18)
"It was above our expectations! It was all very clean and looks nice en beatyfull! "
The price is €314
includes taxes & fees
10 Aug - 11 Aug
Cat Island Suite | Beautifully Renovated w/ Pool!

Waterfront luxury home with private pool

9.8 out of 10, Exceptional, (78)
"We had a wonderful stay at 3/4 time! It is a beautiful VRBO to use in Key West. We truly appreciated all the thoughtful touches that made the place feel like a home away from home.The location was perfect, and the space was clean, comfortable, and well-equipped for a relaxing getaway. We absolueltly loved the heated pool. It was the perfect base for exploring Key West, and we’re already looking forward to our next visit."
Waterfront luxury home with private pool

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (185)
"Quiet area, ocean view, roomy place for family of 3. Will stay again, thank you! "
Direct Oceanfront Cottage-Sunrise View- #2,

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

8.8 out of 10, Excellent, (50)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

The Andros | Incredible Views w/ Shared Pool

8.6 out of 10, Excellent, (18)
"Can’t complain about anything major, but the bed in the right side room had an odd divot in the middle, otherwise comfortable! Great views and location!"
The price is €321
includes taxes & fees
4 Aug - 5 Aug
The Andros | Incredible Views w/ Shared Pool

IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!

9.4 out of 10, Exceptional, (175)
"Really enjoyed the place, very clean and comfortable, great balcony overlooking the ocean. The amenities like the pool and hot tub were very nice and it's a short bike / drive / Lyft from everything in Key West. "
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!

Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing

9.8 out of 10, Exceptional, (128)
"Great property and host. Everything you need for a family especially with small children to be comfortable. The community is quiet and friendly and the space is well maintained. We will be coming back next year. "
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
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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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.