Cudjoe Key Holiday Rentals

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Check prices for these dates

Tonight
30 Jul - 31 Jul
Tomorrow
31 Jul - 1 Aug
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Holiday Rentals in Cudjoe Key

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

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

10.0 out of 10, Exceptional, (3)
"The place was just as pictured, very comfortable and private. Very clean and spacious. The only issue we had was trying to get the back door to lock. "
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
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, (143)
"We had a nice stay at the cottages. Location worked well for our fishing excursions and access across the street to old RT 1 to walk the dogs. "
Cottage with Pool and Boat Dockage just minutes to Key West!
Private Secluded Ocean View & Pool Near Key West
Outdoor pool, a heated pool

Private Secluded Ocean View & Pool Near Key West

8.2 out of 10, Very good, (92)
"We stayed for my husband’s surprise 40th birthday weekend. Kazi was an amazing host and made the booking/arrival/departure process so easy. His hospitality was amazing and we can’t wait to come back."
Private Secluded Ocean View & Pool Near Key West
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, (114)
"Deer in the front yard, perfect location, clean and friendly "
The price is HK$1,766
HK$4,232 total
includes taxes & fees
2 Aug - 3 Aug
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Endless Summer Hideaway - lot 181
Outdoor dining

Endless Summer Hideaway - lot 181

The price is HK$1,334
HK$2,365 total
includes taxes & fees
14 Aug - 15 Aug
Endless Summer Hideaway - lot 181
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby

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

8.8 out of 10, Excellent, (72)
"Very nice quiet place for your lower key vacation. Nice accommodations and easy drive to Key West and Islamorada and several state parks. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
On the beach, sun-loungers, beach towels

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

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 HK$2,826
HK$6,407 total
includes taxes & fees
8 Aug - 9 Aug
Newly Remodeled! Gated Community on Open Water, 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$4,673
HK$8,005 total
includes taxes & fees
2 Aug - 3 Aug
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, (252)
"I love ❤️ this place "
Old Wooden Bridge Resort and Marina
Aqua Lodges at Hurricane Hole Marina
Restaurant

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (160)
"It was a great place to stay! There were a few bugs in the aqua Lodge in the kitchen area, but other than that awesome place!"
The price is HK$622
HK$2,016 total
includes taxes & fees
10 Aug - 11 Aug
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, (818)
"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
Property grounds

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

9.6 out of 10, Exceptional, (77)
"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
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
Marina

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

7.4 out of 10, Good, (10)
"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$2,190
HK$5,809 total
includes taxes & fees
11 Aug - 12 Aug
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!
Pool

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

9.8 out of 10, Exceptional, (209)
"perfect for families with young kids"
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!
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, (7)
"The ideal getaway, I brought a grill and a pan and did all the cooking outside on the deck. Took paddle boards through mangrove tunnels and saw tons of fish. Had a baby sea turtle swim up to the boat. "
The price is HK$1,272
HK$2,100 total
includes taxes & fees
31 Jul - 1 Aug
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Direct Oceanfront Cottage-Sunrise View- #2,
On the beach

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (186)
"Quiet area, ocean view, roomy place for family of 3. Will stay again, thank you! "
Direct Oceanfront Cottage-Sunrise View- #2,
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, (19)
"Place was so clean and perfect location! Very quiet and relaxing"
The price is HK$809
HK$2,747 total
includes taxes & fees
5 Aug - 6 Aug
The Salt Cay | Updated! Stunning Sunset View, Pool!
Cat Island Suite | Beautifully Renovated w/ Pool!
A heated pool

Cat Island Suite | Beautifully Renovated w/ Pool!

10.0 out of 10, Exceptional, (21)
"Great location. Enjoyed our stay!!"
The price is HK$809
HK$2,739 total
includes taxes & fees
10 Aug - 11 Aug
Cat Island Suite | Beautifully Renovated w/ Pool!
Sunshine Key RV Resort & Marina
Kayaking

Sunshine Key RV Resort & Marina

2.0 star property
8.8 out of 10, Excellent, (154)
"I loved staying at Sunshine key"
Sunshine Key RV Resort & Marina
The Andros | Incredible Views w/ Shared Pool
A heated pool

The Andros | Incredible Views w/ Shared Pool

8.6 out of 10, Excellent, (19)
"The short stay we had at your property was absolutely amazing. It is going to be very difficult to top. I can't imagine visiting any other property if I were to come back."
The price is HK$863
HK$2,814 total
includes taxes & fees
17 Aug - 18 Aug
The Andros | Incredible Views w/ Shared Pool
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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Top Cudjoe Key Hotel Reviews

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Location "
Dominick 4-night trip
Posted 21 hours ago
Blue Flamingo Resort Key West

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.