Cudjoe Key Vacations from $686

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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.
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Jul 7 - Jul 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,010 reviews)
Ever think is perfect

Reviewed on Apr 29, 2025

Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Save 100% on your flight
per person
Jul 19 - Jul 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (316 reviews)
Great price per value

Reviewed on Apr 6, 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
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Save 100% on your flight
per person
Jul 19 - Jul 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,270 reviews)
Overall a great experience, but some people really like to scream out loud late at night when you’re trying to relax on the balcony, also cars are loud with music and exhausts… Other than that, the hotel was cute, very friendly staff, I’d come back.

Reviewed on Apr 27, 2025

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
per person
Jul 12 - Jul 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,007 reviews)
We arrived early and our room was ready so we were able to check in. Phillip at the front desk was very friendly and helpful when we asked him for suggestions for things to do. An added bonus was the towels and chairs on the beach were included. Everything is walkable!

Reviewed on Apr 24, 2025

Find the Best Cudjoe Key Vacation Packages

Cudjoe Key Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Population
1,750
Top Sights
Florida Keys Beaches, Sugarloaf Beach and Big Pine Key Flea Market

Ready to book your vacation to Cudjoe Key?

 

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Cudjoe Key Hotel Deals

Cottage with Pool and Boat Dockage just minutes to Key West!
Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
8.4/10 Very Good! (134 reviews)
Quiet getaway
"2nd time and it's a nice relaxing stay.Catch a few fish off the dock or to one of the bridges.And my dogs love it!!"

Reviewed on Apr 5, 2025

Get rates
Cottage with Pool and Boat Dockage just minutes to Key West!
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is $333 per night from May 18 to May 19
$333
includes taxes & fees
$296 per night
May 18 - May 19
8.6/10 Excellent! (1,708 reviews)
"Love the place."

Reviewed on Apr 27, 2025

Margaritaville Beach House Key West
Fairfield Inn and Suites by Marriott Key West
Fairfield Inn and Suites by Marriott Key West
3 out of 5
2400 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is $236 per night from May 26 to May 27
$236
includes taxes & fees
$210 per night
May 26 - May 27
7.8/10 Good! (1,095 reviews)
"I was very excited about visiting this property and hanging out by the pool. However, we weren’t impressed with the friendliness of the staff who drove the shuttle and the pool bartender who closed the bar early with my husband standing there ready to order drinks during Spring Break week. The housekeeping ..."

Reviewed on Apr 20, 2025

Fairfield Inn and Suites by Marriott Key West
See all 1,798 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

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Cudjoe Key vacation package cost?
You’ll find cheap prices from $686 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

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