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.
May-Dee Suites

May-Dee Suites

2.5 out of 5
Hollywood Hills
Save 100% on your flight
per person
Jun. 1 - Jun. 6
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9.4/10 Exceptional! (1,349 reviews)
This is a hidden jewel among the many overrated and over priced hotels/motels nearby. It was very clean and the staff are remarkable.

Reviewed on Apr. 28, 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. 14 - Jul. 18
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Amara Cay Resort

Amara Cay Resort

4 out of 5
Matecumbe
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.8/10 Excellent! (1,216 reviews)
Absolutely breath taking experience. The only thing I would recommend is for the property to have coffe and water available around the clock and for the pool to stay open past sun down.

Reviewed on Apr. 30, 2025

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
7.8/10 Good! (1,006 reviews)
It was a great family resort

Reviewed on Apr. 23, 2025

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Save 100% on your flight
per person
Jun. 19 - Jun. 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
5.8/10 (292 reviews)
The pool was nice, the condo was very basic but was fine. Until the pest control came to spray for roaches. We did not see any roaches during our stay but that did worry us for the rest of our stay. The building is aged but is in a good location.

Reviewed on Mar. 17, 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
8.4/10 Very Good! (134 reviews)
Quiet getaway
"2nd time and it's a nice relaxing stay.Catch a few fish off the dock or to one of the bridges.And my dogs love it!!"

Reviewed on Apr. 5, 2025

Get rates
Cottage with Pool and Boat Dockage just minutes to Key West!
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 $332 per night from May 18 to May 19
CA $332
CA $461 total
includes taxes & fees
May 18 - May 19
8.6/10 Excellent! (1,709 reviews)
"Had a great time thanks"

Reviewed on Apr. 29, 2025

Margaritaville Beach House Key West
Fairfield Inn and Suites by Marriott Key West
Fairfield Inn and Suites by Marriott Key West
3 out of 5
2400 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $256 per night from May 26 to May 27
CA $256
CA $327 total
includes taxes & fees
May 26 - May 27
7.8/10 Good! (1,095 reviews)
"I was very excited about visiting this property and hanging out by the pool. However, we weren’t impressed with the friendliness of the staff who drove the shuttle and the pool bartender who closed the bar early with my husband standing there ready to order drinks during Spring Break week. The housekeeping ..."

Reviewed on Apr. 20, 2025

Fairfield Inn and Suites by Marriott Key West
See all 1,791 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 $427. 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.