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.
Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (911 reviews)
great & friendly staff!!

Reviewed on Aug. 8, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very Good! (1 review)
Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9/10 Wonderful! (2,473 reviews)
Food at the restaurant is good service good

Reviewed on Aug. 9, 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.8/10 Excellent! (1,156 reviews)
It's a very quaint hotel. The rooms are spacious with a living area. The pool is small, but it's a good thing there were not too many people. Great happy hours even during the weekend. I didn't like that they only have valet parking. Albert was the best server at Ocean 2000. And Jennifer and Melissa at the O2K Lounge.

Reviewed on Aug. 10, 2025

Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
9/10 Wonderful! (149 reviews)
We had a great time at the hotel and were impressed with the well-maintained and spacious rooms. The mix of renters, vacationers, and pets on-site created a lively and diverse atmosphere, with everyone being friendly and welcoming. However, there was one issue that I would like to bring to your attention. Some previous tenants or vacationers had let their pets urinate in the common areas, which was unpleasant. Additionally, we noticed a smell in our room’s living room carpet, which was a result of pet urine. As pet owners, we understand the strong odor of pet urine and appreciate it when guests take responsibility for cleaning up after their pets. I hope this feedback helps improve the experience for future guests.

Reviewed on Aug. 4, 2025

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Cudjoe Key Hotel Deals

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

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

Cudjoe Key
The price is CA $172 per night from Aug 27 to Aug 28
CA $172
CA $349 total
Aug 27 - Aug 28
includes taxes & fees
8.4/10 Very Good! (144 reviews)
"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."

Reviewed on Jul. 20, 2025

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

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Aug 12 to Aug 13
CA $185
CA $277 total
Aug 12 - Aug 13
includes taxes & fees
8.4/10 Very Good! (1,437 reviews)
"Beautiful and plenty of room"

Reviewed on Aug. 8, 2025

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Sep 9 to Sep 10
CA $163
CA $261 total
Sep 9 - Sep 10
includes taxes & fees
7.6/10 Good! (1,530 reviews)
"All ok"

Reviewed on Aug. 8, 2025

Blue Flamingo Resort Key West
See all 1,751 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.
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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 $1,163. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.