Cudjoe Key Vacation Packages

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Your Cudjoe Key Vacation

Say bye-bye to the hassle of planning and hello to a Cudjoe Key vacation package. With everything organized before you go, you can focus on discovering this city, starting with Sugarloaf Shores, which is great for families, fishing and views. Make your trip to Cudjoe Key even more fulfilling by including some sightseeing. Florida Keys Beaches, Sugarloaf Beach and Upper Sugarloaf Sound are among the most popular attractions worth exploring. Whoever you're going away with and whether your budget is big or small, your ultimate Cudjoe Key vacation is just a few clicks away with Expedia.

Top Cudjoe Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pelican Hotel

Pelican Hotel

South Beach
CA $976
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.2/10 Wonderful! (490 reviews)
This was a great place for a beach weekend away. The service was excellent, rooms were clean and the food was excellent.

Reviewed on Aug 10, 2026

Casablanca Miami Beach

Casablanca Miami Beach

North Beach
CA $6,961
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
5.8/10 (327 reviews)
Pleas don’t book the apartment in this hotel. It’s not associated with the hotel services. The 2nd room has 3 beds all bed sheets were dirty. The has prior hair from guest before us. Behind the headboard I found a dirty t-shirt. Hall restroom tub was rusted and peeling, I was disgusted to see that. The other restroom still had a long hair in the tub. Sanitary is NOT a priority for the owner of this apartment. The price I paid for my 4 day was a steel. Also, beach gear was a laugh in the face. No beach chair, no wagon and the umbrella covered 1 person. I reached out to the person but never showed up with clean sheets. I had to invest in my stay detergent, sanitizing wipes, trash bags and toilet covers. Let me know forget to say, on my first stay the bottom of my feet was all black from the floors being super dirty. The only good thing of the place was the beach distance.

Reviewed on Jul 23, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach
CA $16,329
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Viscay Hotel

Viscay Hotel

South Beach
CA $2,591
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very good! (341 reviews)
Great location and great value. If you have an early flight before reception opens I’d suggest to arrange check out process beforehand

Reviewed on Jul 16, 2026

Pantera Rosa

Pantera Rosa

South Beach
CA $1,296
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (74 reviews)
The property is great. The location is perfect. The room was outstanding. Checkin is an absolute nightmare!!! Took us an hour from arrival to get our room. It's all done online, nobody to greet you. I saw one person in 4 days on the property. Requested fresh towels sent a text message had to send it again 8 hours later. Finally, got our towels.

Reviewed on Jun 26, 2026

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Cudjoe Key Hotel Deals

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key FL
9.4/10 Exceptional! (175 reviews)
"We thought the grounds and location were perfect centrally located to everything you could want to do in the lower Keys. Host and check in process was extremely smooth and clear from start to finish. The actual cottage/unit needs a thorough cleaning, dishes were dirty and the towels/linens didn’t ..."

Reviewed on Jul 22, 2026

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Cottage with Pool and Dockage, just minutes to Key West
Beachside Resort & Residences

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $149
CA $301 total
Aug 11 - Aug 12
includes taxes & fees
8.6/10 Excellent! (2,419 reviews)
"No housekeeping, the room is not clean and they said that they will charge for housekeeping services. So bad. No private beach as advertised"

Reviewed on Aug 10, 2026

Beachside Resort & Residences
Ibis Bay Beach Resort

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $158
CA $223 total
Aug 11 - Aug 12
includes taxes & fees
8.2/10 Very good! (2,348 reviews)
"Nice property. Didn't love that it was on a busy street but overall a great place to stay. Not close to downtown but if you rent a golf cart it's no problem."

Reviewed on Aug 10, 2026

Ibis Bay Beach Resort
See all 1,787 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.

What to do in Cudjoe Key

Discover US East Coast Self Guided Audio Tour

Discover US East Coast Self Guided Audio Tour

CA $204
per traveller
Discover US East Coast Self Guided Audio Tour
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West

Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West

CA $238
per adult
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
Private Sandbar Adventure in Key West Backcountry

Private Sandbar Adventure in Key West Backcountry

CA $772
per traveller
Private Sandbar Adventure in Key West Backcountry
See all activities in Cudjoe Key

Frequently asked questions

How much does a Cudjoe Key vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Cudjoe Key from just CA $976. 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 vacation 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 Harbor Estates neighborhood, 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 Vacation Rental or Cozy, Perfect Conch Cottage if you prefer this part of town.
How far in advance should I book my Cudjoe Key vacation?
Smart travelers 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 vacation 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 vacation package?
Yes you can, and we're here to help. You may be able to cancel or change your Cudjoe Key vacation 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 vacation, browse our Customer Service Portal for more information.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.