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.
Ocean Villas of Deerfield

Ocean Villas of Deerfield

2.5 out of 5
Save 100% on your flight
per person
Jul. 15 - Jul. 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
9.2/10 Wonderful! (1,009 reviews)
Close to the beach, property kept very clean, swimming pool is a plus.

Reviewed on May 31, 2024

Holiday Isle Yacht Club

Holiday Isle Yacht Club

2.5 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Jul. 15 - Jul. 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
9.2/10 Wonderful! (72 reviews)
Very nice place to stay near the beach l, very beautiful view of bay from room balcony

Reviewed on May 27, 2024

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. 4 - Jul. 8
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
Save 100% on your flight
per person
Jul. 8 - Jul. 12
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.4/10 Very Good! (1,017 reviews)
Beautiful property right on the beach.

Reviewed on May 31, 2024

Hilton Fort Lauderdale Beach Resort

Hilton Fort Lauderdale Beach Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Jul. 15 - Jul. 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8.8/10 Excellent! (1,203 reviews)
The hotel is very nice, the suite we stayed in needs a rug change, or the hotel maids need direction in how to vacuum a rug - crushed cheerios along with a lot of sand on the rug, floor around the credenzas needs to be swept, old cheerios and additional crumbs lying on the floor. Afraid to walk with bare feet in the room. Staff was helpful and nice upon check in. Need to relocate the area for Nube, very inconvenient to tie up an entire elevator for that restaurant/bar on the 26 floor.

Reviewed on May 31, 2024

Cudjoe Key Hotel Deals

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Cudjoe Key
The price is CA $479 per night from Jun. 18 to Jun. 19
CA $479
CA $604 total
includes taxes & fees
Jun 18 - Jun 19
9.6/10 Exceptional! (197 reviews)
Amazing getaway!
"Beautiful and quiet location. Close to Key West yet just far enough to be away from the crowds. Family thoroughly enjoyed it. Everything is as pictured and immaculately clean, truly a gem. Melanie was friendly, always available and always responsive."

Reviewed on May 27, 2024

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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 $219 per night from Jun. 9 to Jun. 10
CA $219
CA $326 total
includes taxes & fees
Jun 9 - Jun 10
8.8/10 Excellent! (1,519 reviews)
"The hotel was great!!! The staff was great. The property is on stock island and set back away from busy streets yet close to everything. Downtown key west was 5 minutes away. We rented a scooter and drove everywhere on that."

Reviewed on May 31, 2024

Oceans Edge Key West Resort, Hotel & Marina
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 $313 per night from Jun. 4 to Jun. 5
CA $313
CA $439 total
includes taxes & fees
Jun 4 - Jun 5
8.4/10 Very Good! (1,770 reviews)
"Can’t thank the front desk and shuttle service enough for their hospitality and amount of care they put into their work. Everyone was so accommodating and made sure we were taken care of. We will be back next time we return to Key West."

Reviewed on May 29, 2024

Margaritaville Beach House Key West
See all 1,596 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 $780. 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.

Discover the most popular places to visit in Cudjoe Key

Image for Bahia Honda State Park

Bahia Honda State Park

Explore the great outdoors at Bahia Honda State Park, a lovely green space in Big Pine Key. While you're in the area, wander around the natural setting.

Bahia Honda State Park
Image for Florida Keys Beaches

Florida Keys Beaches

Why not spend a lazy afternoon at Florida Keys Beaches during your trip to Long Beach Estates?

Florida Keys Beaches
Image for Calusa Beach

Calusa Beach

Why not spend a lazy afternoon at Calusa Beach during your trip to Big Pine Key? While you're in the area, wander around the natural setting.

Calusa Beach

What to do in Cudjoe Key

Image for Private Sandbar Adventure in Key West Backcountry

Private Sandbar Adventure in Key West Backcountry

CA $609
Per adult
Private Sandbar Adventure in Key West Backcountry
Image for Marathon Backcountry Fishing Charter

Marathon Backcountry Fishing Charter

CA $903
Per adult
Marathon Backcountry Fishing Charter
See all activities in Cudjoe Key

Other vacations you might like

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