Cudjoe Key Vacations from $200

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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
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.4/10 Very Good! (795 reviews)
Great hotel for the value you pay. Wilñ definitely come back.

Reviewed on Jun 25, 2025

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.4/10 Very Good! (1,002 reviews)
Very friendly and helpful staff.

Reviewed on Jun 27, 2025

iCoconutGrove Vacation Rentals

iCoconutGrove Vacation Rentals

4 out of 5
Coconut Grove
per person
Sep 14 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
9.2/10 Wonderful! (1,000 reviews)
Very relaxing, & private. Loved it! Very easy to get ahold of management for any needs.

Reviewed on Jun 22, 2025

Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Save 100% on your flight
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
9.2/10 Wonderful! (342 reviews)
A historic and ideally located property right by the beach with a helpful and very accommodating staff. Beautiful renovations highlight the retro-design which creates a relaxing environment of quality and sophistication without feeling too pretentious or haughty. Highly recommended.

Reviewed on Jun 23, 2025

BEST DEAL! 2BR Modern Beachfront Ocean Drive WiFi

BEST DEAL! 2BR Modern Beachfront Ocean Drive WiFi

3 out of 5
South Beach
Save 100% on your flight
per person
Aug 29 - Sep 2
found 14 hours ago
Roundtrip flight included
Philadelphia (PHL) to Miami (MIA)
4/10 (1 review)
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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
$194 nightly
The price is $218 total per night from Jul 1 to Jul 2
$218 total
Jul 1 - Jul 2
Total includes taxes and fees
8.4/10 Very Good! (1,250 reviews)
"We only stayed 2 nights and went to downtown Key West. The room was very clean but extremely small. It was a king bed with a bathroom. We did appreciate the large TV, mini fridge, and the shower/tub was very nice. The shampoo, conditioner, and body wash included was like from a salon. The pool area ..."

Reviewed on Jun 26, 2025

Beachside Resort & Residences
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
$287 nightly
The price is $323 total per night from Jul 13 to Jul 14
$323 total
Jul 13 - Jul 14
Total includes taxes and fees
8.6/10 Excellent! (1,733 reviews)
"Outstanding stay!!! Extremely welcoming staff!! Very accommodating. Food was great. Drinks were flowing. Very laid back relaxing vibe. Jimmy would be proud!!"

Reviewed on Jun 26, 2025

Margaritaville Beach House 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
$204 nightly
The price is $229 total per night from Jun 30 to Jul 1
$229 total
Jun 30 - Jul 1
Total includes taxes and fees
8.8/10 Excellent! (1,669 reviews)
A must stay at least once
"I love this place. We had everything we need in 1 place."

Reviewed on Jun 26, 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 1,744 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 $200 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.