Cudjoe Key Holiday Rentals

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Holiday Rentals in Cudjoe Key

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, (184)
"Loved this ocean view property! Very nice location and very comfortable home!"
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
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, (216)
"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$2,140
HK$5,578 total
includes taxes & fees
23 Nov - 24 Nov
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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, (198)
"The location was perfect and the unit was clean and comfortable. The key lime pie from the hosts was a nice touch."
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, (95)
"Great property. Brought our boat and had a great time. Quick drive to Key Wedt."
The price is HK$1,751
HK$4,157 total
includes taxes & fees
23 Dec - 24 Dec
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
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
Comfortable Waterfront Vacation Rental
Sun-loungers, beach towels
Comfortable Waterfront Vacation Rental
9.4 out of 10, Exceptional, (144)
"Venture Out is a nice place. Cudjoe Key has great restaurant and very friendly people."
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!
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
8.8 out of 10, Excellent, (3)
"Very clean, comfortable beds. Close to everything we wanted to do!"
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, (161)
"The houseboat was a delight. Super comfortable and a full kitchen. Very dog-friendly. The woman who checked us in was super nice, and the salt-water pool felt great!"
The price is HK$1,004
HK$1,908 total
includes taxes & fees
24 Nov - 25 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$1,044
HK$2,269 total
includes taxes & fees
3 Dec - 4 Dec
Aqua Lodges at Hurricane Hole Marina
Poolside Cottage #411
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (30)
"Nice location very close to everything and close enough to Duval St. Unit itself was in good condition and the kitchen stocked pretty good but was missing dish cloths, dish towels and dishwasher detergent. None of the grills on the property were functional. Host was very responsive the entire process. Would stay there again"
The price is HK$1,751
HK$2,962 total
includes taxes & fees
3 Dec - 4 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
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Property grounds
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (14)
"BOOK THIS BOAT!!!’ TOP 10 vacations ever!!! Hannah was so accommodating and onboarded us to The Grand Admiral. Beautiful marina with easy access to The Perry hotel and bar, making it a very very comfortable stay. And then the excursion 😍!! Captain Jeff made our day exceptional. We encountered dolphins, lounged on the sandbar, and grilled while watching a breathtaking sunset. We will be making this an annual trip! Thank you Captain Jeff for the best day ever."
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
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$2,771
HK$3,117 total
includes taxes & fees
7 Dec - 8 Dec
Sunshine Key RV Resort & Marina
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$5,448
HK$6,908 total
includes taxes & fees
8 Dec - 9 Dec
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$15,558
HK$29,196 total
includes taxes & fees
3 Dec - 4 Dec
Real World MTV House-18 to 22 guests, Not Just a House Your Own Private Resort
The Caroline Suite | 1 bed, 1 bath condo w/shared pool
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
The Caroline Suite | 1 bed, 1 bath condo w/shared pool
9.4 out of 10, Exceptional, (12)
"Place was clear, ready, and in a great area. If your looking for a good place in key west this is it"
The price is HK$2,394
HK$4,489 total
includes taxes & fees
15 Dec - 16 Dec
The Caroline Suite | 1 bed, 1 bath condo w/shared pool
The Elizabeth Suite | 1 bed, 1 bath w/shared pool
Interior
The Elizabeth Suite | 1 bed, 1 bath w/shared pool
9.4 out of 10, Exceptional, (3)
"Place was good and clean, has a little pool and laundry out back. But what we didn’t like was the large security deposit and that it took 10 days to refund it. We left the apartment cleaner than we found it. We have all 5 star reviews for years of using other web sites and this also, places all over the world. We think it unnecessary for excellent guests with great reviews. Maybe that could be for new guests and not just for everyone. That was annoying having to ask multiple times for our money...
The Elizabeth Suite | 1 bed, 1 bath w/shared pool
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, (276)
"Adorable place right on the water with beautiful pool to relax at in between wedding commitments …easy location to walk to and from most spots we visited…communication before and during were great with owner Sherri!my first VRBO rental couldn’t have gone smoother!"
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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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, (216)
"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$2,140
HK$5,578 total
includes taxes & fees
23 Nov - 24 Nov
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Margaritaville Beach House Key West
Beach nearby, white sand
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1782)
"X"
The price is HK$1,588
HK$2,277 total
includes taxes & fees
19 Dec - 20 Dec
Margaritaville Beach House Key West
Havana Cabana at Key West - Adults Only
Lobby
Havana Cabana at Key West - Adults Only
4.0 star property
8.8 out of 10, Excellent, (1597)
"Amazing stay! The entire property and rooms are all kept at all times. Every area smells so good too. I can not say enough about the staff; each was was attentive and took pride in their duties to the patrons. Bartenders were next level good! We loved the hen and her baby chicks and the Iguanas that came out to play. We are already planning to go back next year, and this IS where we will be staying. We came for the boat races, next year maybe we'll go earlier so we can enjoy some of the...
The price is HK$1,163
HK$1,803 total
includes taxes & fees
18 Dec - 19 Dec
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.
Beautiful view of the beach with palm trees

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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.