Cudjoe Key Vacations from $372

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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.

The Latest Cudjoe Key vacation packages

Price found within the past 48 hours. Click for updated prices.
Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was $722, price is now $372 per person
$372
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (818 reviews)
Beach staff was rude.

Reviewed on Sep 8, 2025

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $1,846, price is now $873 per person
$873
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Great staff. Nice rooms close to beach

Reviewed on Sep 2, 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 $26,855, price is now $12,827 per person
$12,827
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
President Hotel

President Hotel

3.5 out of 5
South Beach
Price was $1,823, price is now $890 per person
$890
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,825 reviews)
We weren’t informed in advanced that the pool was closed for renovation or repair. We paid a resort fee and this is one of the amenities. It would’ve been nice to use the pool on our arrival day in the afternoon or early evening until it closed. The second day it rained it didn’t matter, but it’s the point that this happened without being informed.

Reviewed on Sep 18, 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was $1,431, price is now $704 per person
$704
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (961 reviews)
It took like 45 minutes to get my car back from the valet people which was really annoying.

Reviewed on Sep 20, 2025

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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
$737 nightly
The price is $818 total per night from Sep 21 to Sep 22
$818 total
Sep 21 - Sep 22
Total with taxes and fees
9.6/10 Exceptional! (230 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
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
$192 nightly
The price is $216 total per night from Sep 28 to Sep 29
$216 total
Sep 28 - Sep 29
Total with taxes and fees
8.8/10 Excellent! (1,720 reviews)
"Excellent Property"

Reviewed on Sep 14, 2025

Oceans Edge Key West Resort, Hotel & Marina
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
$195 nightly
The price is $219 total per night from Sep 24 to Sep 25
$219 total
Sep 24 - Sep 25
Total with taxes and fees
8.4/10 Very Good! (1,539 reviews)
"Pool could be colder!"

Reviewed on Sep 18, 2025

Beachside Resort & Residences
See all 1,760 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?
You'll find cheap prices from $372 on Expedia for your Cudjoe Key getaway. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Cudjoe Key costs.
What are the cheapest months to go to Cudjoe Key?
You're likely to find lower prices and better availability in April, May and June. Browse our cheap Cudjoe Key vacation packages and you could get some great off-season deals.
How many days is enough for Cudjoe Key?
With a well-planned itinerary, you can easily tick off the main Cudjoe Key attractions in a handful of days. But if you'd like to discover hidden spots or go on day trips, consider booking your Cudjoe Key vacation for longer.
How to find the best Cudjoe Key package deals?
Use Expedia's filters to help you find some great Cudjoe Key package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Cudjoe Key package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Cudjoe Key vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still get the flexibility to create a tailored Cudjoe Key vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Cudjoe Key?
If you've got your Cudjoe Key travel dates finalized, book as early as you can to grab some incredible deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Cudjoe Key?

  1. Choose when to go: Check your calendar and pack your bags. Your favorite season and the type of activities on offer will also help you decide when to escape to Cudjoe Key.
  2. Set your budget: Consider expenses such as flights, food and transportation when calculating how much to save for your trip to Cudjoe Key. Then, select a hotel that works with your budget, whether that's a low-cost option or a swankier retreat.
  3. Use Expedia's trip planning tool to discover Cudjoe Key: Research every aspect of your trip to Cudjoe Key with this comprehensive planner. Invite family or friends to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Decide how many days away: Start by compiling a list of the sights and activities you want to get to in Cudjoe Key. Then, estimate how long you'll need at each, as well as any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalized Cudjoe Key vacation package.
  6. Book any activities or day trips: Here's the fun part — locking in everything you want to see and do. Explore some of the top things to do in Cudjoe Key and reserve your tickets early to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Cudjoe Key vacation packages?
Set off on your perfect escape to Cudjoe Key with Expedia's Book Now, Pay Later vacations. No need to save up or wait for your next paycheck — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to budget for your trip and snap up bargains before they disappear.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.