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.
Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
per person
Oct 13 - Oct 17
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (2,401 reviews)
Room very small. And garage situation is difficulty due to elevator upgrades. Hopefully it will be better soon.

Reviewed on Jul. 30, 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
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Flow Miami Hotel

Flow Miami Hotel

3.5 out of 5
Downtown Miami
per person
Sep 23 - Sep 30
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (136 reviews)
Room was not fully equipped and bathroom was not clean

Reviewed on Aug. 1, 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
Oct 13 - Oct 17
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
Needs new sheets They felt like they had small balls from being super used Place need new bed with prosper new linen I stayed at a TownePlace for three nights that had better mattress and linen

Reviewed on Aug. 1, 2025

Aloha Fridays

Aloha Fridays

3 out of 5
South Beach
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8.4/10 Very Good! (36 reviews)
Friendly and kind staff. (that was the highlight) Nice room. Great location.

Reviewed on Jul. 26, 2025

Ready to book your vacation to Cudjoe Key?

 

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Cudjoe Key Hotel Deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Aug 12 to Aug 13
CA $185
CA $278 total
Aug 12 - Aug 13
includes taxes & fees
8.4/10 Very Good! (1,399 reviews)
"Wow I would definitely be back What an amazing time Love the views the nicely kept property All round 5 stars"

Reviewed on Jul. 30, 2025

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Sep 1 to Sep 2
CA $168
CA $266 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (1,490 reviews)
"Good value for your money, convenient location and a friendly, welcoming staff. As a pet friendly resort, perhaps in the future have a couple of dog friendly entertainment areas on the resort so owners and their fur babies can spend time together."

Reviewed on Jul. 29, 2025

Blue Flamingo Resort Key West
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 $210 per night from Aug 13 to Aug 14
CA $210
CA $316 total
Aug 13 - Aug 14
includes taxes & fees
8.8/10 Excellent! (1,700 reviews)
"I really loved the whole experience from beginning to end! The receptionist are awesome and very pleasant to speak to all the staff are very pleasant and we really really enjoyed our stay"

Reviewed on Jul. 29, 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 1,734 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.
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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 $674. 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.