Cudjoe Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
B Ocean Resort Fort Lauderdale Beach

B Ocean Resort Fort Lauderdale Beach

4 out of 5
East Fort Lauderdale
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
7.6/10 Good! (3,010 reviews)
Convenient and cozzy resort. Friendly staff and great service. Beach and close to lots of things to do.

Reviewed on Aug. 3, 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 6 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Miami (MIA)
8/10 Very Good! (1 review)
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 - Oct 31
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,154 reviews)
The food options weren’t the best. Very pricey and not many options. The beds were very comfy though.

Reviewed on Aug. 3, 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.4/10 Exceptional! (8 reviews)
Stayed at the new Shelbourne Hotel in Miami Beach and honestly everything was great. The front desk staff was super friendly and helpful, which set the tone right away. The pool was calm and peaceful—such a nice vibe. Everything felt fresh and clean. Definitely would come back.

Reviewed on Jul. 31, 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
per person
Oct 6 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Miami (MIA)
8.2/10 Very Good! (906 reviews)
Everything was perfect. Truly a 5 star hotel. Beach service was very welcomed and done perfectly.

Reviewed on Aug. 3, 2025

Ready to book your vacation to Cudjoe Key?

 

Choose your dates

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
8.4/10 Very Good! (143 reviews)
Perfect
"An amazing place to come home to after a long day in the keys. Having a car is a must, but I would recommend time after time again and hope to come back again in the future"

Reviewed on Jun. 10, 2025

Get rates
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 $177 per night from Aug 24 to Aug 25
CA $177
CA $269 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (1,410 reviews)
"Staff was very helpful, room was clean, shuttle to downtown was awesome. We loved the Tavern and Town restaurant on site. Great food and priced right at happy hour!"

Reviewed on Aug. 1, 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 $168 per night from Sep 2 to Sep 3
CA $168
CA $266 total
Sep 2 - Sep 3
includes taxes & fees
7.6/10 Good! (1,511 reviews)
"Nice pool and courtyard with games, good A/C, quiet rooms, and a great location. However, breakfast was a big disappointment: waited 20–30 minutes just to order, then another 20+ for food, all while workers were using loud tools just a meter away. Shower water was only lukewarm, not hot. At 2 PM, ..."

Reviewed on Aug. 1, 2025

Blue Flamingo Resort Key West
See all 1,734 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $913. 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.