Cudjoe Key Vacation Rentals

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Vacation Rentals in Cudjoe Key

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
9.2 out of 10, Wonderful, (174)
"Great location, 23 miles to Key West. View from deck is breathtaking."
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
9.8 out of 10, Exceptional, (202)
"Fantastic property and location, our 2nd time there. Melanie, the host, is super responsive. I would highly recommend."
The price is CA $478
CA $603 total
includes taxes & fees
May 29 - May 30
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Cudjoe Key, FL RV Resort RV Lot
8.0 out of 10, Very good, (4)
"Had a wonderful stay"
The price is CA $130
CA $173 total
includes taxes & fees
May 16 - May 17
Cudjoe Key, FL RV Resort RV Lot
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Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very good, (89)
"Good place. 3 bed rooms all with Queen size beds. It was perfect for us. We sat on the porch mostly when we were there and played games. Not a long ride to Key West. Overall- we were happy and would stay there again."
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
9.8 out of 10, Exceptional, (182)
"Very nice"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Cozy, Perfect Conch Cottage!
9.2 out of 10, Wonderful, (29)
"Our stay was great! The description is accurate. We enjoyed our 6 Mid-March days at "Cozy Perfect Conch Cottage." Yes, it's technically camping, but it's very NICE camping...in a campground...but a very NICE campground. The bed we used (there were only 2 of us) was super comfortable. The WiFi worked great. It was awesome having a full kitchen and washer/dryer. The towels were plentiful, soft and luxurious. Linens were also very soft and comfortable. Everything needed for basic cooking was...
Cozy, Perfect Conch Cottage!
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
9.8 out of 10, Exceptional, (217)
"My daughter and I stayed in Cudjoe Key to be close to Key West. The location was good. The unit had everything we needed both inside and out. We grilled and cooked which was great. The beds were comfortable. Unfortunately, the weather did not cooperate and excursions were cancelled so we spent more time in Key West than we had planned. But the unit had lots of games and the TV had the tennis channel which was very nice. All in all, it was a good time."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Comfortable Waterfront Vacation Rental
9.4 out of 10, Exceptional, (138)
"Excellent stay. Very comfortable."
Comfortable Waterfront Vacation Rental
Tropical Getaway in Paradise.
9.4 out of 10, Exceptional, (80)
"The property was everything it said in the listing. It was clean, comfortable and a grest place to sit and relax after a day full of adventures. We were visiting our son who lives on Summerland Key and works for the Boy Scouts. It was centrally located so we could go east or west and explore. Thanks for making this trip enjoyable, and relaxing. Sincerely, the Meyers'"
Tropical Getaway in Paradise.
3 night minimum! Spectacular Ocean Views!
8.2 out of 10, Very good, (15)
"Unit was slightly smaller than what we were expecting by the pictures. Very clean, except for the floor in main area. Walking around left the soles of your feet very dirty. Used mop that was provided and it cleaned up nicely. When roll-out bed was out, there was no room to maneuver in the room. Everything worked as expected. Neighborhood was quiet and nice. Manager was responsive and very helpful. A lot of amenities were provided and appreciated."
3 night minimum! Spectacular Ocean Views!
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
2.5 star property
8.4 out of 10, Very good, (121)
"Loved the view. House was ok. But the soap!!! Ugh. Understand that it is necessary for water boats but just never felt clean. Personal thing. Won't stop us from coming back tho :-)"
The price is CA $184
CA $344 total
includes taxes & fees
May 16 - May 17
Old Wooden Bridge Resort and Marina
Sunshine Key RV Resort & Marina
2.0 star property
8.8 out of 10, Excellent, (129)
"Family oriented, quite and safe. "
Sunshine Key RV Resort & Marina
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is CA $295
CA $504 total
includes taxes & fees
May 28 - May 29
Poolside Cottage #411
52' Power Catamaran Yacht at Luxury Resort Marina
10.0 out of 10, Exceptional, (11)
"We had a great time about Blue Jeans! Louie is an amazing host, as responsive as possible, also took us out for a cruise around Key West, AC works great! Easy Golf kart ride from the marina to down town key west. Pool at the marina was nice as well."
52' Power Catamaran Yacht at Luxury Resort Marina
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (85)
"Aqualodges was a unique, great experience. Really enjoyed the marine life right at our dock. The accommodations were clean and comfortable. Cant wait to come back! "
The price is CA $234
CA $456 total
includes taxes & fees
May 20 - May 21
Aqua Lodges at Hurricane Hole Marina
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (9)
"Sunset cruise was amazing around key west with captain lombardi"
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (24)
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (257)
"This property and host exceeded all of our expectations. It was spacious, comfortable, and welcoming with its amazing kitchen, breezy rooms, and friendly neighbors. The hosts were a pleasure to work with and easy to reach whenever we wished to communicate with them. 10/10 would return to this property. I highly recommend it!"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
40'yacht in Paradise Awaits You!
9.6 out of 10, Exceptional, (23)
"We had a really nice couple of days on this boat. We are older (over 60), and we weren't sure if it was going to be our thing. It was good though! The host was amazingly helpful. We loved the private beach and pool right around the corner. We have been to Key West a lot, so we didn't need to do all the tourist stuff. We mostly stayed on Stock Island. It was easy to get Ubers, so we didn't bother with a car or golf cart. If we were staying longer, we probably would have rented a golf cart. The...
40'yacht in Paradise Awaits You!
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See all available properties in Cudjoe Key
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.

Cudjoe Key Vacation Rental Travel Info

Number of vacation rentals
17
Popular accommodation
Cudjoe Key private vacation homes
Known landmarks
Florida Keys Beaches, Sugarloaf Beach and Big Pine Key Flea Market
International airport
Key West, FL (EYW-Key West Intl.)

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

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (202)
"Fantastic property and location, our 2nd time there. Melanie, the host, is super responsive. I would highly recommend."
The price is CA $478
CA $603 total
includes taxes & fees
May 29 - May 30
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Cudjoe Key, FL RV Resort RV Lot
8.0 out of 10, Very good, (4)
"Had a wonderful stay"
The price is CA $130
CA $173 total
includes taxes & fees
May 16 - May 17
Cudjoe Key, FL RV Resort RV Lot
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1513)
"Amazing fun quiet great room food was excellent kayaking and bike rides were fun too! Highly recommend "
The price is CA $261
CA $373 total
includes taxes & fees
May 21 - May 22
Oceans Edge Key West Resort, Hotel & 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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Cudjoe Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Cudjoe Key?

Yes, we give you a choice of vacation rentals close to well known points of interest in Cudjoe Key, or you can choose a more remote option if you're looking for relaxation. Cudjoe Key is known for its seafood restaurants and seaside.

What's the top vacation rental that Cudjoe Key has to offer?

3 night minimum! Spectacular Ocean Views!: This Cudjoe Key vacation home rental offers a balcony, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Our travelers also rate Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West as a favorite home for rent in Cudjoe Key.

How many vacation rentals are there in Cudjoe Key?

With 205 Expedia vacation rentals, you're sure 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 larger area.

What are vacation rentals like in Cudjoe Key?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Cudjoe Key. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.

Recent reviews of Cudjoe Key properties
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