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Top Holiday Rentals in Cudjoe Key

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

9.8 out of 10, Exceptional, (223)
"We loved our stay here! This place had everything that we needed. The resort was safe for my kids to roam around for pickleball, swimming, and fishing. Thank you!"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (146)
"Clean cottage, very helpful host, comfortable beds, great location --enjoyable stay."
Cottage with Pool and Dockage, just minutes to Key West

Private Secluded Ocean View & Pool Near Key West

8.2 out of 10, Very good, (92)
"Property was as advertised "
Private Secluded Ocean View & Pool Near Key West

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (247)
"Clean, easy access, friendly complex/neighborhood. "
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

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

8.8 out of 10, Excellent, (143)
"My sister and friend from north Alabama and my youngest daughter and I decided on a last minute mini vacation. We found this little gem of a place while looking for places to stay in the Keys. Although it could use some TLC, we found the property to be clean, well-stocked and perfect for a short stay, some family time, rest and relaxation. We truly enjoyed our stay and would definitely consider staying here again,"
Cudjoe Cottages, swimming pool, just 20 miles from Key West

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

8.4 out of 10, Very good, (113)
"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. "
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (148)
"Would definitely stay here again! "
The price is £184
includes taxes & fees
22 Jun - 23 Jun
Aqua Lodges at Hurricane Hole Marina

Old Wooden Bridge Resort and Marina

2.5 star property
8.6 out of 10, Excellent, (240)
"price - clean and newly renovated boats - nice staff - easy check in/out."
Old Wooden Bridge Resort and Marina

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very good, (814)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

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

8.0 out of 10, Very good, (9)
"Kevin and Capt. Phil were great hosts. Would definitely stay there again. "
The price is £429
includes taxes & fees
12 Jul - 13 Jul
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

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

9.4 out of 10, Exceptional, (173)
"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!

CLASSIC HATTERAS MOTOR YACHT LOCATED AT THE PERRY MARINA, A 5-STAR RESORT.

The price is £345
includes taxes & fees
18 Jul - 19 Jul
CLASSIC HATTERAS MOTOR YACHT LOCATED AT THE PERRY MARINA, A 5-STAR RESORT.

Resort View 1BR Suite

2.0 star property
10.0 out of 10, Exceptional, (2)
"Cleanliness "
The price is £281
includes taxes & fees
1 Jul - 2 Jul
Resort View 1BR Suite

GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

9.8 out of 10, Exceptional, (40)
"Property was well maintained and nice folks in the community. Recommend highly!"
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w/ Pool and Ocean Views!

Cat Island Suite | Beautifully Renovated w/ Pool!

10.0 out of 10, Exceptional, (14)
"Great location. Enjoyed our stay!!"
The price is £301
includes taxes & fees
22 Jun - 23 Jun
Cat Island Suite | Beautifully Renovated w/ Pool!

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

9.8 out of 10, Exceptional, (204)
"The place is beautiful and every convenience thought of. Would definitely stay here Asian! "
ATLANTIC BREEZE ~ 2B/2BA Renovated Retreat w/ Pool, Fitness Area & Beach!

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

8.8 out of 10, Excellent, (49)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

Poolside Cottage #411

9.8 out of 10, Exceptional, (45)
"Lovely home to stay in for a couple of nights on Key West"
The price is £259
includes taxes & fees
22 Jun - 23 Jun
Poolside Cottage #411

Island View 1BR Residence With Balcony

2.0 star property
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
The price is £278
includes taxes & fees
1 Jul - 2 Jul
Island View 1BR Residence With Balcony

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

9.8 out of 10, Exceptional, (287)
"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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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.