Cudjoe Key Vacations from $335

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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
per person
Oct 15 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
A Perfect Stay on Ocean Drive I had a wonderful stay at this hotel right on Ocean Drive in South Beach. The location is unbeatable—just steps from the beach and in the heart of all the action. The customer service was attentive and friendly, always ready to help with a smile. The on-site restaurant was a pleasant surprise—great food, good vibes, and drinks. The decor throughout the hotel is stylish and inviting, with that classic South Beach charm. Highly recommend for anyone looking to soak up the Miami vibe in comfort and style!

Reviewed on Jul 31, 2025

Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
per person
Oct 8 - Oct 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
Needs new sheets They felt like they had small balls from being super used Place need new bed with prosper new linen I stayed at a TownePlace for three nights that had better mattress and linen

Reviewed on Aug 1, 2025

Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
per person
Oct 15 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (800 reviews)
friendly staff, clean rooms, 1 block away from the beach

Reviewed on Jul 22, 2025

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
Oct 15 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,329 reviews)
My family and I spent one night before heading back home. Everything went really well. Carmen at the Front Desk was very helpful! I would recommend this property.

Reviewed on Jul 31, 2025

Aloha Fridays

Aloha Fridays

3 out of 5
South Beach
Save 100% on your flight
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (36 reviews)
Friendly and kind staff. (that was the highlight) Nice room. Great location.

Reviewed on Jul 26, 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
$190 nightly
The price is $214 total per night from Aug 10 to Aug 11
$214 total
Aug 10 - Aug 11
Total includes taxes and fees
8.4/10 Very Good! (1,403 reviews)
"excellent"

Reviewed on Jul 30, 2025

Beachside Resort & Residences
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
$172 nightly
The price is $193 total per night from Sep 1 to Sep 2
$193 total
Sep 1 - Sep 2
Total includes taxes and fees
7.6/10 Good! (1,488 reviews)
"Good value for your money, convenient location and a friendly, welcoming staff. As a pet friendly resort, perhaps in the future have a couple of dog friendly entertainment areas on the resort so owners and their fur babies can spend time together."

Reviewed on Jul 29, 2025

Blue Flamingo Resort Key West
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
$218 nightly
The price is $246 total per night from Aug 18 to Aug 19
$246 total
Aug 18 - Aug 19
Total includes taxes and fees
8.8/10 Excellent! (1,700 reviews)
"I really loved the whole experience from beginning to end! The receptionist are awesome and very pleasant to speak to all the staff are very pleasant and we really really enjoyed our stay"

Reviewed on Jul 29, 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 1,734 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 $335 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.