Cudjoe Key Holiday Rentals

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Check prices for these dates

Tonight
21 Apr - 22 Apr
Tomorrow
22 Apr - 23 Apr
This weekend
25 Apr - 27 Apr
Next weekend
2 May - 4 May

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, (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!
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$2,328
HK$4,917 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, (144)
"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
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
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, (216)
"third time staying here well stocked and clean, property manager could not be more helpful."
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)
"Was very quiet & relaxing! Great location to middle & lower keys."
The price is HK$2,134
HK$5,562 total
includes taxes & fees
22 Apr - 23 Apr
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Ocean/Canal Views 21ft Dock - Venture Out #357
Terrace/patio

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
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$3,929
HK$7,136 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)
"We liked seeing the key deer and the grass mat out front was soft on the feet. We arrived after the office closed and discovered the hot water was not turned on when we arrived so we had to figure out how to turn on with a switch. My brother-in-law figured this out. The water would go from cool to warm off and on during showers. Not sure why."
The price is HK$1,079
HK$1,990 total
includes taxes & fees
28 Apr - 29 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, (130)
"It was a great experience being on a houseboat."
The price is HK$756
HK$2,152 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
28 Apr - 29 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! "
The price is HK$1,164
HK$4,580 total
includes taxes & fees
6 May - 7 May
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. "
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$1,738
HK$2,929 total
includes taxes & fees
27 Apr - 28 Apr
Poolside Cottage #411
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)
"We had a great time!! We hope to be back next year."
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
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$1,292
HK$3,643 total
includes taxes & fees
27 Apr - 28 Apr
The Salt Cay | Updated! Stunning Sunset View, Pool!
Sunshine Key RV Resort & Marina
Sun deck

Sunshine Key RV Resort & Marina

2.0 star property
8.8 out of 10, Excellent, (146)
"I enjoyed staying in a tiny house. The property was amazing!"
Sunshine Key RV Resort & Marina
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, (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!
Beachside Resort & Residences
Outdoor pool, pool umbrellas, pool loungers

Beachside Resort & Residences

3.5 star property
8.4 out of 10, Very good, (1024)
"Property on a very busy and noisy corner. All traffic enters and leaves Key West here. The facility is very nice, excellent service and easy parking. Pool and surroundings nice. The beach area is not a real beach. Resort is clean all round. Would stay again if can’t stay in old town Key West. "
The price is HK$1,607
HK$2,200 total
includes taxes & fees
20 May - 21 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, (1734)
"A pretty hotel with a laidback relaxed vibe. Very clean and all workers were super friendly and helpful. The Resturant and bar was very good and made great drinks. The pool area was clean and fun but pool was a bit small for us. The hot tube happen to be broken when we were there. The tropical courtyard area was lovely and we loved that a full on gorgeous beach was right across the street complete with chairs and umbrellas and floats to rent. We really had a nice stay at this hotel. "
The price is HK$2,173
HK$2,941 total
includes taxes & fees
11 May - 12 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.