Cudjoe Key Holiday Rentals from €245: Search Short-Term Rentals

Q: 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.

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Holiday Rentals in Cudjoe Key

"Drove From CLE to The Keys with my dog and enjoyed the quietness of the property. 30 an hour from Key West. Great rate. Would recommend. "

includes taxes & fees

26 Feb - 27 Feb

"Lovely two bedroom waterfront property is reminiscent of a beachfront cottage in New England or the Outer Banks. If you're expecting a Marriott timeshare on an expensive island in the Caribbean as some of the previous reviews seemed to be then then perhaps look elsewhere. But if you want a comfortable winter escape in an absolutely perfect location both within the resort as well as where it is in the Keys then this is for you. We enjoyed the beautiful view from both the upper deck as well as...

"It was a very cute and small place to stay. My husband and I are very tall and felt a little cramped in the bathroom otherwise our stay was great. Check in and out was simple. "

includes taxes & fees

25 Mar - 26 Mar

"We enjoyed our stay, would stay again. Communication was excellent. Property is just as pictured. Great location, great value for the price. Could use a little freshening up, light bulb in laundry room, etc."

includes taxes & fees

2 Mar - 3 Mar

"Three employees traveling in the Keys stayed and all reported their complete satisfaction with the accommodations and location. Thank you!"

includes taxes & fees

25 Feb - 26 Feb

"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. "

includes taxes & fees

28 Feb - 1 Mar

"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."

includes taxes & fees

5 Mar - 6 Mar

"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"

On the beach, sun-loungers, beach towels

"Great week in the Florida Keys. Home was extremely clean, very well equipped, had everything you needed to make you feel at home. Each bedroom had it's own ensuite bath and it was perfect for two couples. Location was excellent and would not hesitate to book here again.Thanks Melanie!"

includes taxes & fees

22 Mar - 23 Mar

"This house is beautiful, it’s an old Keys style home, nautical, clean, beautiful views, we spent most of our time in the pool. Great place to just get away and relax. Love that is was off the beaten path. The palm trees, coconuts and yard is beautiful. The owner answered us almost immediately for any needs or questions we had. Will definitely make this a yearly trip. "

"Very clean, comfortable beds. Close to everything we wanted to do!"

"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "

includes taxes & fees

26 Mar - 27 Mar

"Enjoy being on the water, having a full kitchen, access to all water activities, stores, and a walkable access to a restaurant. Loved it and have plans to do it again!"

includes taxes & fees

2 Mar - 3 Mar

2 Bedroom Aqua Lodge # 13 Barracuda | Living area

"Everything about it was great"

includes taxes & fees

24 Feb - 25 Feb

"Great location, clean, and good customer service. wish they had fishing rods and more to do around the property, and the AC didn't keep the upstairs cool, very hot up there at night. overall, happy about the stay."

"I didn’t really know what I was getting into, but I’m glad I didn’t cancel. This was such a beautiful experience to have shared with just myself. The bed was comfortable and I slept really well both nights. The second night, I had to rent a kayak from the marina (40) to get to the house. It was a beautiful sunset paddle. It’s easy enough, but even as an experienced paddler, it’s about 20 minutes . I had to leave around 5am to catch my flight and paddled back to the marina in pitch black. It was...

includes taxes & fees

27 Feb - 28 Feb

"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! "

includes taxes & fees

2 Mar - 3 Mar

"Quiet area close to everything we were looking for. "

includes taxes & fees

3 Mar - 4 Mar

"We had a bunch of guys stay here recently while we were in town for a fishing trip. We also had the penthouse at The Perry hotel but ended up spending more time on on the 3rd deck roof of the boat! It's an older boat but very cool with lots of character, plenty of room 8 guys in their 30s to sleep with everyone getting their own bed. It's hard to beat the location and price honestly! We rented golf carts from the hotel used those to explore the beaches and downtown area. The marina is only 10...

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Other types of properties in Cudjoe Key you may be interested in

"Lovely two bedroom waterfront property is reminiscent of a beachfront cottage in New England or the Outer Banks. If you're expecting a Marriott timeshare on an expensive island in the Caribbean as some of the previous reviews seemed to be then then perhaps look elsewhere. But if you want a comfortable winter escape in an absolutely perfect location both within the resort as well as where it is in the Keys then this is for you. We enjoyed the beautiful view from both the upper deck as well as...

"It was a very cute and small place to stay. My husband and I are very tall and felt a little cramped in the bathroom otherwise our stay was great. Check in and out was simple. "

includes taxes & fees

25 Mar - 26 Mar

"Very clean, comfortable beds. Close to everything we wanted to do!"

Find out more about Cudjoe Key

Everything you need to know about Cudjoe Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cudjoe Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cudjoe Key holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cudjoe Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cudjoe Key. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cudjoe Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cudjoe Key holiday rentals we have selected for you start as low as €245 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cudjoe Key rentals

At Expedia, we put the best Cudjoe Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cudjoe Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cudjoe Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cudjoe Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of Cudjoe Key properties

Oceans Edge Key West Resort, Hotel & Marina

5/5 Excellent

"Nice"

A verified traveller stayed at Oceans Edge Key West Resort, Hotel & Marina

Posted 14 hours ago

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

5/5 Excellent

Terrific oceanfront property

"Lovely two bedroom waterfront property is reminiscent of a beachfront cottage in New England or the Outer Banks. If you're expecting a Marriott timeshare on an expensive island in the Caribbean as some of the previous reviews seemed to be then then perhaps look elsewhere. But if you want a comfortable winter escape in an absolutely perfect location both within the resort as well as where it is in the Keys then this is for you. We enjoyed the beautiful view from both the upper deck as well as the shielded downstairs patio (beautiful sunrise), grilled several times and swam every day in the community pool and the ocean. We'll be back."

A verified traveller stayed at Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Posted 2 days ago

5/5 Excellent

"I enjoyed my stay here very much. There are a lot of friendly staff working to keep this place clean and fresh looking. The beach, restaurant and pool were great. Loved the hammocks everywhere. Walking distance to shopping centers and other restaurants. The hourly shuttle to/from Duval St is awesome. You can rent a lot of things out of the resort too, bikes,etc. I would just mention there is no room service as described, nor is there a shuttle to the airport as a previous review stated. There is Uber and other Taxi services available however. Will go again. Truly loved it."

A verified traveller stayed at Ibis Bay Beach Resort

Posted 2 days ago

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All accommodation types in Cudjoe Key

Holiday Homes in Cudjoe Key

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.

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Holiday Rentals in Cudjoe Key

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Check prices for these dates

Holiday Rentals in Cudjoe Key

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West

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

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

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

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

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

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

Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West

FL Keys Cottage with Ocean Views - Venture Out Unit 395

FL Keys Cottage with Ocean Views - Venture Out Unit 395

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

Coconut Mallory Resort And Marina By Kees Vacations

Coconut Mallory Resort And Marina By Kees Vacations

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

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

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

Resort View 1BR Suite

Resort View 1BR Suite

Poolside Cottage #411

Poolside Cottage #411

TRAVEL THE KEYS OR JUST RELAX AT THE DOCK

TRAVEL THE KEYS OR JUST RELAX AT THE DOCK

Other types of properties in Cudjoe Key you may be interested in

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!

FL Keys Cottage with Ocean Views - Venture Out Unit 395

FL Keys Cottage with Ocean Views - Venture Out Unit 395

Find out more about Cudjoe Key

Find out more about Cudjoe Key

Recent reviews of Cudjoe Key properties

Recent reviews of Cudjoe Key properties

Oceans Edge Key West Resort, Hotel & Marina

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends