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

4 out of 5
South Beach
Save 100% on your flight
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9.2/10 Wonderful! (341 reviews)
The hotel was very clean and the service was wonderful; however, the mattress caused

Reviewed on May 12, 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
Jul 19 - Jul 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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
Jul 22 - Jul 29
found 2 days ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8.8/10 Excellent! (1,088 reviews)
The hotel is family friendly. Rooms are spacious and umbrellas and chairs on the beach are a plus.

Reviewed on Jun. 14, 2025

The Shelborne By Proper

The Shelborne By Proper

4 out of 5
South Beach
Save 100% on your flight
per person
Aug 23 - Aug 30
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
10/10 Exceptional! (3 reviews)
Everything was amazing- The accommodations, the property decor, the staff like Adrian and Chef Luis were very personable and welcoming. Our room was upgraded from partial ocean view to full as we were celebrating our 23rd wedding anniversary, so that was a nice touch. We would definitely book again.

Reviewed on May 31, 2025

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Jul 23 - Jul 30
found 2 days ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
9.2/10 Wonderful! (1,175 reviews)
Beautiful rooms, gym and pools!

Reviewed on Jun. 15, 2025

Ready to book your vacation to Cudjoe Key?

 

Choose your dates

Cudjoe Key Hotel Deals

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 $194 per night from Jun 17 to Jun 18
CA $194
CA $288 total
Jun 17 - Jun 18
includes taxes & fees
8.4/10 Very Good! (1,180 reviews)
"M"

Reviewed on Jun. 14, 2025

Beachside Resort & Residences
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $294 per night from Jun 29 to Jun 30
CA $294
CA $416 total
Jun 29 - Jun 30
includes taxes & fees
8.6/10 Excellent! (1,716 reviews)
"Love the property this was our 3rd time staying there has everything the family needs"

Reviewed on Jun. 14, 2025

Margaritaville Beach House Key West
Oceans Edge Key West Resort, Hotel & Marina
Oceans Edge Key West Resort, Hotel & Marina
4 out of 5
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Jun 25 to Jun 26
CA $199
CA $355 total
Jun 25 - Jun 26
includes taxes & fees
8.8/10 Excellent! (1,666 reviews)
"The property is beautiful, quiet and shuttle was a plus. The staff are very friendly. Loved our visit and plan to return! Thank you for the experience."

Reviewed on Jun. 12, 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 1,744 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 $1,028. 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.