Cudjoe Key Holiday Rentals

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Holiday Rentals in Cudjoe Key

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, (215)
"the property it is good but expedia say good price for cleaning and vrbo say higher price i not agree, because i believed all time that cleaning it is the price said Expedia thanks , but i never rent or recommend again thanks"
The price is HK$2,137
HK$5,530 total
includes taxes & fees
10 Nov - 11 Nov
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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, (95)
"Great property. Brought our boat and had a great time. Quick drive to Key Wedt."
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
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, (196)
"We had a wonderful time for a quick Labor Day weekend trip. The neighborhood is family friendly and we enjoyed riding the bikes to the pool with our kids. It was convenient to have the boat ramp in the community as well. The house was clean, comfortable and well stocked. Thank you for sharing your home with us! "
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Outdoor dining
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
9.0 out of 10, Wonderful, (181)
"The view was wonderful. Great place to see sunrise every morning. This was a girls trip. If you are just there for fishing, this place is perfect. The refrigerator and freezer smelled of fish. Even after 3 nights, the smell was strong. I recommend bringing some arm and hammer baking soda for both fridge and freezer. The place is pretty close to Key West, so location is great. The neighbors were cleaning their fish right off the dock, so there were many seagulls. With seagulls, comes poop. They...
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Comfortable Waterfront Vacation Rental
Sun-loungers, beach towels
Comfortable Waterfront Vacation Rental
9.4 out of 10, Exceptional, (143)
"Our annual trip never disappoints. Property always has what we need and is perfectly located."
Comfortable Waterfront Vacation Rental
3 night minimum! Spectacular Ocean Views!
A heated pool
3 night minimum! Spectacular Ocean Views!
8.4 out of 10, Very good, (18)
"Venture out is a great location for being on the water. This rental was reasonable, spacious and clean! We had an amazing stay with no issues!"
3 night minimum! Spectacular Ocean Views!
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Exterior
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, (230)
"Very clean and quiet. Great amenities. Friendly staff. Would stay there again and recommend to our friends."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Tropical Getaway in Paradise.
Outdoor pool, a heated pool
Tropical Getaway in Paradise.
9.4 out of 10, Exceptional, (83)
"Venture Out resort is nice and this cozy trailer is good!"
Tropical Getaway in Paradise.
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Fridge, microwave, oven, stovetop
FL Keys Cottage with Ocean Views - Venture Out Unit 395
8.0 out of 10, Very good, (2)
"Great location and nice park amenities. Kids really liked the Venture Out pool."
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Old Wooden Bridge Resort and Marina
Living area
Old Wooden Bridge Resort and Marina
2.5 star property
8.4 out of 10, Very good, (158)
"A cute apartment and a beautiful place, but charging 100 dollars for cleaning to a person who rented an apartment for only one night is an exaggeration in my opinion. Calculation of cost should be the ratio of their stay to the number of nights."
The price is HK$1,002
HK$1,905 total
includes taxes & fees
10 Nov - 11 Nov
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, (104)
"Nice for affordable price "
The price is HK$875
HK$2,078 total
includes taxes & fees
11 Nov - 12 Nov
Aqua Lodges at Hurricane Hole Marina
Sunshine Key RV Resort & Marina
Sun deck
Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (141)
"Nice place to relax"
The price is HK$2,766
HK$3,112 total
includes taxes & fees
6 Dec - 7 Dec
Sunshine Key RV Resort & Marina
Poolside Cottage #411
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (27)
"Nice STAY"
The price is HK$1,368
HK$2,474 total
includes taxes & fees
30 Nov - 1 Dec
Poolside Cottage #411
34’ Catamaran Sailboat
Interior
34’ Catamaran Sailboat
9.6 out of 10, Exceptional, (27)
"Overall it was a great experience."
34’ Catamaran Sailboat
ATLANTIC HIDEAWAY- Key West
Outdoor pool, a heated pool
ATLANTIC HIDEAWAY- Key West
9.8 out of 10, Exceptional, (42)
"Great place, highly recommend"
ATLANTIC HIDEAWAY- Key West
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, (275)
"I don’t want this published but the only problem we had was with the bikes. They were not in great shape but everything else was well taken care of. "
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
The Crystalmarine Suite – Rustic Luxury on the Sea
Interior
The Crystalmarine Suite – Rustic Luxury on the Sea
10.0 out of 10, Exceptional, (2)
"This VRBO is a dream for those looking to escape the hustle and bustle of everyday life. With its unique location, it provides a perfect blend of adventure and relaxation. Whether you're looking to reconnect with nature or simply unwind in a beautiful setting, this floating house offers an unparalleled experience."
The price is HK$5,440
HK$6,842 total
includes taxes & fees
24 Nov - 25 Nov
The Crystalmarine Suite – Rustic Luxury on the Sea
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
Aerial view
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
9.6 out of 10, Exceptional, (81)
"Very well run property/operation. The house has tons of things to do and was ideal four our bachelor party. Definitely recommend"
The price is HK$15,534
HK$29,345 total
includes taxes & fees
11 Nov - 12 Nov
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
One of the very few beach houses with a daily, rental license in the Keys.
Outdoor pool
One of the very few beach houses with a daily, rental license in the Keys.
9.0 out of 10, Wonderful, (54)
"We stayed here with another family, so we had a total of 13 people. The view is beautiful. The pool and tiki hut and pool table are was awesome for our family to hang out. It doesn’t have any shade right by the pool but the tiki hut and pool table area were shaded. The second king bedroom is upstairs after walking up spiral staircase. There is no private door- it’s kind of like a loft. And then there’s a bunk room that is off of the king bedroom upstairs so if you want privacy, good luck. The...
The price is HK$4,655
HK$10,320 total
includes taxes & fees
10 Nov - 11 Nov
One of the very few beach houses with a daily, rental license in the Keys.
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Terrace/patio
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
9.0 out of 10, Wonderful, (30)
"Peaceful and paradise!"
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
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

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, (215)
"the property it is good but expedia say good price for cleaning and vrbo say higher price i not agree, because i believed all time that cleaning it is the price said Expedia thanks , but i never rent or recommend again thanks"
The price is HK$2,137
HK$5,530 total
includes taxes & fees
10 Nov - 11 Nov
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Beachside Resort & Residences
Outdoor pool, pool umbrellas, pool loungers
Beachside Resort & Residences
3.5 star property
8.4 out of 10, Very good, (1010)
"Excellent place to stay! "
The price is HK$1,504
HK$2,085 total
includes taxes & fees
3 Dec - 4 Dec
Beachside Resort & Residences
Havana Cabana at Key West - Adults Only
Outdoor pool, pool loungers
Havana Cabana at Key West - Adults Only
4.0 star property
8.8 out of 10, Excellent, (1599)
"Friendly staff, great place to stay!"
The price is HK$1,281
HK$1,937 total
includes taxes & fees
20 Nov - 21 Nov
Havana Cabana at Key West - Adults Only
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.