Cudjoe Key Vacations from $447

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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.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
Price was $869, price is now $447 per person
$447
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,004 reviews)
Room was clean. Staff was friendly beach, restaurants and shops nearby. Also a convenient parking garage within walking distance.

Reviewed on Nov 4, 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was $1,685, price is now $725 per person
$725
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (39 reviews)
Fantastic experience. One of the best hotels we have stayed at. Shout out to Jenny, Marta , Shane and Louis, William and Josh and all of the other wonderful staff. Definitely recommend it and will certainly go back !

Reviewed on Nov 1, 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 $22,801, price is now $11,044 per person
$11,044
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Canada House Beach Club Resort

Canada House Beach Club Resort

2 out of 5
Save 100% on your flight
Price was $1,026, price is now $527 per person
$527
per person
Jan 18 - Jan 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (42 reviews)
Everything was great

Reviewed on Nov 4, 2025

EAST Miami Residences

EAST Miami Residences

5 out of 5
Downtown Miami
Price was $1,839, price is now $967 per person
$967
per person
Jan 8 - Jan 12
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (78 reviews)
Staff were very helpful and courteous! Amenities were excellent and room was cleaned everyday. Location was the best.

Reviewed on Nov 3, 2025

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Cudjoe Key Hotel Deals

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
$206 nightly
The price is $232 total per night from Nov 16 to Nov 17
$232 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (1,733 reviews)
We’ve stayed here twice now. Staff is great, the shuttle into town is super convenient (hi Jeffrey!). We love that you can use the kayaks or paddleboards every day. The tiki hut crew is the best! The place is clean and I feel safe walking around there. It’s well lit and easy to navigate.

Reviewed on Nov 2, 2025

Oceans Edge Key West Resort, Hotel & Marina
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
$157 nightly
The price is $177 total per night from Nov 18 to Nov 19
$177 total
Nov 18 - Nov 19
Total with taxes and fees
7.8/10 Good! (1,648 reviews)
Beautiful room, great view, love the pools, bars and lawn games

Reviewed on Nov 3, 2025

Blue Flamingo Resort Key West
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
$193 nightly
The price is $217 total per night from Nov 12 to Nov 13
$217 total
Nov 12 - Nov 13
Total with taxes and fees
8.6/10 Excellent! (1,655 reviews)
Staff good but never clean our room

Reviewed on Nov 3, 2025

Beachside Resort & Residences
See all 1,791 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.

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

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Frequently asked questions

How much does a Cudjoe Key vacation package cost?
You'll find cheap prices from $447 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.

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