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.
Avalon Hotel

Avalon Hotel

3.5 out of 5
South Beach
Price was CA $779, price is now CA $375 per person
CA $375
per person
Oct 26 - Oct 30
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9.2/10 Wonderful! (1,018 reviews)
At first glance it was a little older than I expected. But it was very clean and staff was great Very close to everything you need and want

Reviewed on Aug. 21, 2025

Riverside Hotel

Riverside Hotel

3.5 out of 5
East Fort Lauderdale
Price was CA $1,422, price is now CA $630 per person
CA $630
per person
Oct 26 - Oct 30
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
9/10 Wonderful! (2,500 reviews)
First time there. Definitely will return.

Reviewed on Aug. 19, 2025

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 $1,319, price is now CA $599 per person
CA $599
per person
Oct 26 - Oct 30
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8.8/10 Excellent! (1,193 reviews)
Great private beach location.

Reviewed on Aug. 24, 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was CA $1,171, price is now CA $555 per person
CA $555
per person
Oct 26 - Oct 30
found 10 hours ago
Roundtrip flight included
Detroit (DTW) to Miami (MIA)
8.2/10 Very Good! (930 reviews)
I appreciated the close location to the beach. We were literally a walk across the street to the beach. Everything was walkable. The staff were attentive & present. Very helpful and friendly & accommodating. The lobby area always was clean smelling. I liked they provided complimentary bikes to ride, beach chairs & bottled water. What I did not like were the little bit of channels available on the tv. The stations they did have did not have service so it did not work. Would also recommend a full length mirror.

Reviewed on Aug. 23, 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 $33,908, price is now CA $16,416 per person
CA $16,416
per person
Nov 5 - Nov 10
found 9 hours ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
8/10 Very Good! (1 review)

Ready to book your vacation to Cudjoe Key?

 

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Cudjoe Key Hotel Deals

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes

Cudjoe Key
The price is CA $484 per night from Aug 25 to Aug 26
CA $484
CA $1,130 total
Aug 25 - Aug 26
includes taxes & fees
9.6/10 Exceptional! (229 reviews)
Beautiful place!
"The house is absolutely beautiful! You cannot beat the location. We met the owner while we were at the gated community and he was very accommodating. You can kayak right out back, there are great views from the pool which was kept nice and cool during the summer. We highly recommend this place. Just ..."

Reviewed on Aug. 21, 2025

Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
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 $173 per night from Aug 25 to Aug 26
CA $173
CA $265 total
Aug 25 - Aug 26
includes taxes & fees
8.4/10 Very Good! (1,474 reviews)
"I decided to go with this property despite some negative reviews and I am so glad i did. The entire stay was perfect. Staff was so nice and helpful. Special shout out to Ro for making sure we were taken care of. Definitely book again!"

Reviewed on Aug. 20, 2025

Beachside Resort & Residences
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 $232 per night from Sep 2 to Sep 3
CA $232
CA $341 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (1,726 reviews)
"This property was wonderful! Absolutely gorgeous!"

Reviewed on Aug. 23, 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 1,747 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 $375. 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.