Cudjoe Key Holidays
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Top Flight + Hotel Deals in Cudjoe Key
Price found within the past 48 hours. Click for updated prices.
Villa Italia by At Mine Hospitality
South Beach
€358
per person
8 Nov - 11 Nov
found 17 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
9.8/10 Exceptional! (87 reviews)
It was a great stay the room was clean we were offered housekeeping. The staff was very accommodating asking if we needed anything & how our stay is going. Ocean drive was two blocks away which was very convenient. It was also very cool inside the building since it’s really hot outside. Overall great stay.
Reviewed on 1 Sept 2026
Top hotels in Cudjoe Key
Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key FL
9.4/10 Exceptional! (176 reviews)
"This location is very convenient for me as my family lives 5 miles from this place. Very clean and the host works well with the customer."
Reviewed on 2 Aug 2026
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
€176
10 Sept - 11 Sept
includes taxes & fees
8.6/10 Excellent! (2,483 reviews)
"Hot tub wasn’t working. It was just warm water. Gym was very hot. Beach wasn’t great. Elevator in my building wasn’t working g but you can use the one from the building next to it and walk over. So not that bad. Pool was great. Never crowded. Room was excellent. We had a suite with pool access. There ..."
Reviewed on 1 Sept 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
€227
16 Sept - 17 Sept
includes taxes & fees
8.8/10 Excellent! (1,800 reviews)
"Outdoor pool and beach access are nice. A little far from old town, but you can use shuttle every hour."
Reviewed on 2 Sept 2026
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.
What to do in Cudjoe Key
Discover US East Coast Self Guided Audio Tour
€125
per traveller
Private Sandbar Adventure in Key West Backcountry
€432
per traveller
Frequently asked questions
How much does a Cudjoe Key holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Cudjoe Key from just €358. And the more you bundle, the more dollars you save. Your dream escape has never been so affordable.
How do I get a cheap travel package to Cudjoe Key?
Booking a Cudjoe Key holiday package with Expedia is an easy way to save. We have more than 550 air carriers and 1,000,000 hotel options around the globe. With such a fabulous range to select from, you'll have no issues putting together your ideal adventure.
Where should I stay in Cudjoe Key?
There's so much to see in Cudjoe Key, so spend your evenings near its attractions and spend more time sightseeing. Upper Sugarloaf Key is one spot to add to your must-see list.
What are the top hotels in Cudjoe Key?
If you're thinking of staying in the Cutthroat Harbour Estates neighbourhood, some of your best options are Judy's Place At Venture Out and Dog - Friendly Resort Community Home With Pool. Cudjoe Gardens is also a popular Cudjoe Key area. We recommend Comfortable Waterfront Holiday Rental or Cosy, Perfect Conch Cottage if you prefer this part of town.
How far in advance should I book my Cudjoe Key holiday?
Smart travellers will likely want to book as early as possible. You can normally look up international airfares on Expedia up to a year before your flight. If you're booking at the last minute, fear not. Discounted prices occasionally appear in the last weeks prior to departure.
What does an Expedia Cudjoe Key travel package include?
Expedia has all you need to arrange your Cudjoe Key trip, but how your package is structured is your choice. Choose from any combination of hotels, flights and rental cars. Chasing some tours or experiences to keep you on the move? Once you've made your booking, you can add them on too. Whatever your style, there's a deal to match your needs.
What should I know before booking a Cudjoe Key travel package?
So many places to visit, so many things to see and do. With a package, you'll be able to tick more of them off your list. Bundle your flights, rental cars and hotels and make big savings.
Can I choose my airline with a Cudjoe Key Expedia holiday package?
You can, and with over 550 airlines to choose from all over the world, you have plenty of choice. Take a look at the available options and see which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Cudjoe Key holiday package?
Yes you can, and we're here to help. You may be able to cancel or change your Cudjoe Key holiday package for free within 24 hours of booking. But you may be charged a fee by your airline, hotel or car rental company for older bookings. If life gets in the way of your holiday, browse our Customer Service Portal for more information.
Explore a world of travel with Expedia
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- Visit Doctor's Arm
- Visit Eden Pines
- Big Pine Key Flea Market
- Big Pine Key Holidays
- Visit Big Pine Key
- Visit Boca Chica Key
- Boca Chica Nude Beach
- Captain Hooks Marina and Dive Center
- Coco Plum Beach
- Visit Cudjoe Key
- Custom House Museum
- Duval Street
- Ernest Hemingway Home and Museum
- Fort East Martello Museum and Gallery
- Fort Zachary Taylor Historic State Park
- Harry S. Truman Little White House
- Key West Butterfly and Nature Conservatory
- Key West Lighthouse and Keeper's Quarters Museum
- Key West Holidays
- Visit Little Torch Key
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- Kid friendly Holiday Packages Key Haven
- Mallory Square
- Marathon Holidays
- Museum of Art & History at the Custom House
- Key West Historic District
- Robbie's
- San Carlos Institute - Casa Cuba
- Seven Mile Bridge
- Simonton Beach
- Smathers Beach
- Sombrero Beach
- Visit Stock Island
- Visit Sugarloaf Key
- Visit Summerland Key
- Sunset Park Beach
- Ace New Zealand Rental Cars in Boca Chica Key
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- Car hire near Robbie's
- Dollar Rent A Car Rental Cars in Boca Chica Key
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- Goldcar rental Rental Cars in Lower Keys
- National Car Rental Rental Cars in Lower Keys
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
