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.
The Local House

The Local House

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug. 23 - Aug. 26
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9/10 Wonderful! (1,001 reviews)
Beautiful place to stay close to the beach. Excellent staff, decor and restaurant

Reviewed on Jun. 11, 2024

1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
per person
Aug. 23 - Aug. 26
found 24 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9/10 Wonderful! (1,004 reviews)
Everything about this property was perfect. The view from the balcony, the staff, the room, absolutely PERFECT.

Reviewed on Jun. 17, 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
Sep. 5 - Sep. 9
found 7 hours ago
Roundtrip flight included
Vancouver (YVR) to Miami (MIA)
8/10 Very Good! (1 review)
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug. 20 - Aug. 27
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.4/10 Very Good! (651 reviews)
Great location and so close to the beach. You can walk on Ocean drive and explore the streets without being far from the hotel.

Reviewed on Jun. 1, 2024

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug. 20 - Aug. 27
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very Good! (1,002 reviews)
Juan at the front reception was amazingly professional and informative during my check in as well as during my entire stay of 8 nights. Housekeeping ladies amazing as well. Everyone at the Cavalier restaurant were great as well. Overall I had an excellent stay. Location was perfectly close to everything... I will stay here again. Thank you, Sergio G. Las Vegas. NV

Reviewed on Jun. 13, 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 $480 per night from Jul. 13 to Jul. 14
CA $480
CA $609 total
includes taxes & fees
Jul 13 - Jul 14
9.6/10 Exceptional! (198 reviews)
Great Location-Great Stay
"This property is in a great location in the FL Keys. The space was clean and well-appointed with everything you need for a great stay. The grounds are well maintained have access to the water and a very nice pool area. We enjoyed the kayaks and fishing on the dock. Restaurants are a very short drive ..."

Reviewed on Jun. 15, 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 $229 per night from Jun. 30 to Jul. 1
CA $229
CA $338 total
includes taxes & fees
Jun 30 - Jul 1
8.8/10 Excellent! (1,524 reviews)
"Yearly trip"

Reviewed on Jun. 14, 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 $273 per night from Jul. 14 to Jul. 15
CA $273
CA $394 total
includes taxes & fees
Jul 14 - Jul 15
8.4/10 Very Good! (1,804 reviews)
Great staff and facilities
"Staff, all of them were awesome. Facility was clean, looked to be in good condition."

Reviewed on Jun. 16, 2024

Margaritaville Beach House Key West
See all 1,617 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 $481. 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

4.5/5(29 reviews)

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
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.