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.
Flow Miami

Flow Miami

2 out of 5
Downtown Miami
Save 100% on your flight
per person
Jul. 23 - Jul. 30
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9/10 Wonderful! (74 reviews)
This is the perfect stay for couples and family ! I can’t wait to be back with my children !

Reviewed on Apr. 28, 2025

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. 23 - Jul. 30
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8.6/10 Excellent! (1,010 reviews)
Ever think is perfect

Reviewed on Apr. 29, 2025

Eden Roc Miami Beach

Eden Roc Miami Beach

4.5 out of 5
Mid Beach
per person
Jul. 23 - Jul. 30
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8.4/10 Very Good! (2,387 reviews)
Loved my stay (which I extended) at Eden Roc. I was fortunate to have the most amazing view, and I did not want to leave. Candidly, I also needed to stay another night as the late checkout policy was not great... All the staff were very friendly. I was busy at an event so I did not take advantage of any of the amenities. I had a slight issue with the furniture/lighting in my room. And am happy I booked with Expedia at a discounted rate but overall much enjoyed.

Reviewed on Apr. 30, 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
per person
Jul. 23 - Jul. 30
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8/10 Very Good! (5,944 reviews)
It is a 5-star. Beach and pool are amazing. but they did not provide coffee machine in the room. You need to pay for everything here which you usually get for free when you stay Marriott or Hilton. Overall it is a happening place.

Reviewed on Apr. 30, 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
Jul. 23 - Jul. 30
found 17 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8.2/10 Very Good! (1,331 reviews)
The only thing was the people that hung out around and across the street from the hotel front door was locked after hour but there where people using the side door to come in. And the sister pool stayed pack and no place to relax

Reviewed on Apr. 30, 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! (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 $252 per night from Jun. 1 to Jun. 2
CA $252
CA $323 total
includes taxes & fees
Jun 1 - Jun 2
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 $696. 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.