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.
Avi Lux Stay
East Fort Lauderdale
CA $1,498
per person
Nov 16 - Nov 23
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
7.6/10 Good! (10 reviews)
If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.
Reviewed on Aug 28, 2025
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $25,652
per person
Dec 23 - Dec 28
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
The Penguin Hotel
South Beach
CA $1,587
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.4/10 Very good! (1,996 reviews)
There is a resort fee per day, on top of 150 they need for the room Just an fyi. The front desk ladies were very helpful and nice but the one of the over night men couldn’t have a worse attitude up front I wish I got his name. The pool closes at 7 and it’s not located at this hotel it’s at the building behind it and the bar is also located not actually at this hotel. Elevator worked but very loud so we heard it every time it went up or down. And the walls are paper thin so it didn’t help.They say it’s every 3 days they clean but knocked on our door every morning and the lady was very friendly. Wasn’t the worst hotel I’ve stayed in but I don’t think I’ll be back. Only plus is the location because the beach being across the street
Reviewed on Oct 15, 2026
President Hotel Villa
South Beach
CA $1,652
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very good! (1,000 reviews)
It felt really cozy. Its in a prime location to everything. I would return.
Reviewed on Oct 16, 2026
Ready to book your vacation to Cudjoe Key?
Cudjoe Key Hotel Deals
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key FL
8.8/10 Excellent! (184 reviews)
"Cottage was clean. We enjoyed the stay. Needs an outlet cover in living room."
Reviewed on Sep 28, 2026
Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key FL
9/10 Wonderful! (174 reviews)
"This location was perfect for what my husband and I needed. We brought our boat and were able to use the dock throughout our stay. We did have an issue with the AC system and Jennifer was great by putting us into another one of their units overnight until our units AC was fixed the next day. This ..."
Reviewed on Jul 24, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $290
CA $415 total
Oct 30 - Oct 31
includes taxes & fees
8.8/10 Excellent! (1,794 reviews)
"Very nice and friendly staff. It was a great place."
Reviewed on Oct 16, 2026
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.
What to do in Cudjoe Key
Discover US East Coast Self Guided Audio Tour
CA $203
per traveller
Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
CA $236
per adult
Private Sandbar Adventure in Key West Backcountry
CA $699
per traveller
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 $1,498. 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
