Cudjoe Key Vacations from $525

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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
Price was $1,083, price is now $525 per person
$525
per person
Jan 16 - Jan 21
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (952 reviews)

Avi Lux Stay

Avi Lux Stay

4.5 out of 5
East Fort Lauderdale
Price was $2,216, price is now $978 per person
$978
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.6/10 Good! (10 reviews)
If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.

Reviewed on Aug 28, 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 $20,316, price is now $9,557 per person
$9,557
per person
Jan 19 - Jan 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Private Oasis at Arya

Private Oasis at Arya

3.5 out of 5
Coconut Grove
Price was $1,751, price is now $935 per person
$935
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,071 reviews)

501 First - Rooftop Pool - Gym

501 First - Rooftop Pool - Gym

2.5 out of 5
Downtown Miami
Price was $1,350, price is now $724 per person
$724
per person
Jan 17 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
No reviews

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What to do in Cudjoe Key

Marathon Backcountry Permit

Private Marathon Backcountry Fishing Charter

$750
per adult
Private Marathon Backcountry Fishing Charter
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

$41
per adult
88% of travellers recommend
Key West Conch Tour Train
Key West's Island Eco Tour: Kayaking, Snorkeling & Sandbar Adventure

Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour

$130
per adult
98% of travellers recommend
Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
See all activities in Cudjoe Key

Cudjoe Key Hotel Deals

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Cudjoe Key FL
8.8/10 Excellent! (186 reviews)
"Finding the property by GPS is not easy. Turning at the truck sign works."

Reviewed on Oct 19, 2026

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Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!

Cudjoe Key FL
9/10 Wonderful! (175 reviews)
"The view from the docks was great. Convenient location to go to all the key islands. Very relaxing. Enjoyed our stay for sure."

Reviewed on Oct 13, 2026

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Cottage with swimming pool and dockage, just minutes to Key West!
Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!

Cudjoe Key FL
8.6/10 Excellent! (170 reviews)
"This is an old quaint property.Right on the Atlanticside.Two docks.The pool is modern and very nice.Cottage is ideal for two.Old but clean"

Reviewed on Oct 27, 2026

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Cottage with Pool and Boat Dockage just minutes to Key West!
See all 1,806 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 $525 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.