Longwood Vacations from $256

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Your Longwood Vacation

From its highlights to its hidden delights, this city is best experienced with a Longwood vacation package. Find somewhere to stay in Ivanhoe Village, which is good for dining, bars and pubs and shopping. You'll want to sightsee during your trip to Longwood. Find time for famous attractions like Altamonte Mall, Winter Park Village and Cranes Roost Park. Whatever your travel plans or budget, putting together a tailored Longwood vacation is a breeze with Expedia.

The Latest Longwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $599, price is now $256 per person
$256
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
17.6/10 Exceptional! (3,229 reviews)
Staff was great. The room was clean

Reviewed on Nov 19, 2025

Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,896, price is now $625 per person
$625
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
17.2/10 Exceptional! (1,002 reviews)
Clean room expected amenities

Reviewed on Nov 12, 2025

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $1,022, price is now $412 per person
$412
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18/10 Exceptional! (1,681 reviews)
From the minute we checked in and Michelle greeted us, we knew we picked the right spot! Since it’s quiet season, they were able to upgrade our room to double balcony oceanfront. It felt like we were right over the beach! Very clean rooms and facilities. We were visiting my nephew who goes to school at DSC and the valet guys were so accommodating, allowing us to leave the car out front for a few hours here and there without charging us the parking fee. Sore isl shout out to Dom from valet. The pool area was great and we loved the tiki bar (shout out to Doug the bartender!) he even gave me a special drink for my bday!!! They give s’mores kits at night to use at the pool side fire pits too! When we come back to visit, we will definitely rebook at the Shores!!!

Reviewed on Nov 16, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $761, price is now $317 per person
$317
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
16/10 Exceptional! (1,367 reviews)
from the staff to the clean rooms and all the fun things in the resort... WAS GREAT!!!!

Reviewed on Nov 18, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was $1,631, price is now $696 per person
$696
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
18.4/10 Exceptional! (1,001 reviews)
The place is exceptional and met all of our needs and then some

Reviewed on Nov 12, 2025

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Discover the most popular places to visit in Longwood

Alaqua Country Club

Enjoy a round of golf in Longwood at Alaqua Country Club. While you're in the area, stroll along the lakeside.

Alaqua Country Club

The Legacy at Alaqua Lakes

Enjoy a round of golf in Longwood at The Legacy at Alaqua Lakes. Stroll along the area's lakeside or experience its entertainment choices.

The Legacy at Alaqua Lakes

Aiguille Rock Climbing Center

You can take time to visit Aiguille Rock Climbing Center during your travels to Longwood. Experience the area's entertainment choices or attend a sporting event.

Aiguille Rock Climbing Center

What to do in Longwood

Orlando: Central Florida Zoo Skip-the-Line Ticket

Orlando: Central Florida Zoo Skip-the-Line Ticket

$22
per adult
Orlando: Central Florida Zoo Skip-the-Line Ticket
Pony rides for the littlest cowboys and cowgirls!

Barn Day for Little Cowboys and Cowgirls

$5
per adult
Barn Day for Little Cowboys and Cowgirls
Wekiva River Guided Kayak Tour

Wekiva River Guided Kayak Tour

$100
per adult
Wekiva River Guided Kayak Tour
See all activities in Longwood

Find the Best Longwood Vacation Packages

Longwood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Orlando Intl. Airport (MCO)
Population
14,100
Max Temp Winter
70ºF
Max Temp Summer
90ºF
Top Sights
Central Florida Zoo & Botanical Gardens, Sanford Museum and Wayne Dench Performing Arts Center

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Frequently asked questions

How much does a Longwood vacation package cost?
You'll find cheap prices from $256 on Expedia for your Longwood break. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Longwood costs.
What are the cheapest months to go to Longwood?
July, August and December are great times to search for cheap Longwood vacation packages. Opting to travel in less busy months means you can usually find reduced prices on flights and hotels.
How many days is enough for Longwood?
Usually, a handful of days is enough to check out the top sights during your Longwood vacation. But if you prefer to have time to rest or go on day tours, consider extending your trip.
Is it worth booking a vacation package to Longwood?
It's easy to see why a Longwood vacation is on the must-do list of many travelers. Leading attractions like Boombah-Soldiers Creek Park are just the beginning of things to see and do here.
How to find the best Longwood package deals?
Landing a cheap Longwood package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Longwood package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Longwood vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component separately. And you'll still get the freedom to create a customized Longwood vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Longwood?
If you're considering a spontaneous Longwood adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Longwood?

  1. Choose when to go: Check your calendar and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to visit Longwood.
  2. Figure out your budget: Make sure you have enough money to pay for everything from meals and transportation to flights and experiences. Your hotel will likely be the biggest expense during your trip to Longwood.
  3. Organize your Longwood escape with Expedia's trip planning tool: Search for and book hotels and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Longwood together.
  4. Decide your trip length: Think about how long you'd like to spend exploring Longwood. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  5. Combine your airfare and accommodations: Once you've settled on your travel dates and duration, book the ideal Longwood vacation package for you.
  6. Book any day trips or activities: Here's the fun part — organizing everything you want to do and see. Browse some of the incredible things to do in Longwood and book your tickets early to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Longwood vacation packages?
Your Longwood getaway should be a relaxing escape from your busy life, not a reason for money worries. So to allow you a bit more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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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.