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
Price was CA $1,247, price is now CA $612 per person
CA $612
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Miami (MIA)
9/10 Wonderful! (2,473 reviews)
First time there. Definitely will return.

Reviewed on Aug. 19, 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
Price was CA $22,592, price is now CA $10,212 per person
CA $10,212
per person
Oct 11 - Oct 16
found 6 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) 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
Price was CA $1,355, price is now CA $677 per person
CA $677
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Buffalo (BUF) to Miami (MIA)
8.8/10 Excellent! (1,156 reviews)
What a great experience, the whole staff was amazing I very recommend this place to stay

Reviewed on Aug. 19, 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was CA $1,715, price is now CA $888 per person
CA $888
per person
Nov 7 - Nov 11
found 9 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Miami (MIA)
8.2/10 Very Good! (911 reviews)
Had a great stay here . Very nice clean place . Would definitely recommend. Thanks Eric ( Day Manager )

Reviewed on Aug. 20, 2025

EAST Miami Residences

EAST Miami Residences

5 out of 5
Downtown Miami
Price was CA $4,350, price is now CA $2,473 per person
CA $2,473
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9/10 Wonderful! (70 reviews)
This place is very beautiful, greats views with great customer service. This place just makes you feel very comfortable like your at home

Reviewed on Aug. 20, 2025

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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 $176 per night from Aug 26 to Aug 27
CA $176
CA $268 total
Aug 26 - Aug 27
includes taxes & fees
8.4/10 Very Good! (1,468 reviews)
gorgeous view
"It was so nice—we ended up with a gorgeous view."

Reviewed on Aug. 18, 2025

Beachside Resort & Residences
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Aug 27 to Aug 28
CA $140
CA $197 total
Aug 27 - Aug 28
includes taxes & fees
7.8/10 Good! (1,066 reviews)
"Nice hotel"

Reviewed on Aug. 14, 2025

Hilton Garden Inn Key West / The Keys Collection
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 $171 per night from Aug 25 to Aug 26
CA $171
CA $270 total
Aug 25 - Aug 26
includes taxes & fees
7.6/10 Good! (1,545 reviews)
Pretty good for budget
"Was clean and friendly staff, shuttle driver were also nice, the pool was awesome and so was the bar. Only thing is I thought there was a balcony but it is more of a motel set up. But the rooms are comfy and very coast home inspired"

Reviewed on Aug. 17, 2025

Blue Flamingo Resort Key West
See all 1,758 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
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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 $612. 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.