Longwood Vacations from $247

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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.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $439, price is now $247 per person
$247
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,684 reviews)
Lo mejor. Me encantó súper recomendado.

Reviewed on Sep 30, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,371, price is now $687 per person
$687
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
8.8/10 Excellent! (486 reviews)
They messed up my reservation for our second and third days by putting my name incorrectly. I was called out of the pool in front of all the guests in the middle of the dayand made to go to the front desk. Only to find we had to scurry to pack our belongings and moved to another room. No fault of ours yet we were left to fend for ourselves. . It took 1 1/2 hours of prime day with our friends. It was humiliating and beyond inconvenient. We were compensated with 2 free drinks tickets. Judge for yourself if this was proper and professional.

Reviewed on Sep 28, 2025

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
Price was $716, price is now $361 per person
$361
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.4/10 Very Good! (1,001 reviews)
There was a very shady old looking red car parked outside our windows with loud music playing late into the night our last two nights

Reviewed on Aug 19, 2025

Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
Save 100% on your flight
Price was $1,050, price is now $549 per person
$549
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
8.2/10 Very Good! (386 reviews)
The hotel was good but now with the water park and other amenities it’s even better. My grandkids loved it, it was s great experience for them and something very different to other hotels in Fl

Reviewed on Sep 16, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Save 100% on your flight
Price was $607, price is now $322 per person
$322
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (1,012 reviews)
Very child friendly. The staff was fine and it is very convenient to get to Universal!

Reviewed on Oct 9, 2025

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Discover the most popular places to visit in Longwood

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

The Trophy Club Of Orlando

Enjoy a round of golf in Wekiva Springs at The Trophy Club Of Orlando. Discover the area's top-notch restaurants and its acclaimed theater scene.

The Trophy Club Of Orlando

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

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
Wekiva River Guided Kayak Tour

Wekiva River Guided Kayak Tour

$100
per adult
Wekiva River Guided Kayak Tour
Rock Springs 2-Hour Glass Bottom Guided Kayak Eco Tour

Rock Springs 2-Hour Glass Bottom Guided Kayak Eco Tour

$99
per adult
100% of travellers recommend
Rock Springs 2-Hour Glass Bottom Guided Kayak Eco Tour
See all activities in Longwood

Longwood Hotel Deals

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard, Orlando, FL
Fully refundableReserve now, pay when you stay
$180 nightly
The price is $203 total per night from Oct 20 to Oct 21
$203 total
Oct 20 - Oct 21
Total with taxes and fees
9.4/10 Exceptional! (3,628 reviews)
"Staff very helpful and friendly. They help get you to your cruise pick up and do it with a smile. Had a great stay. Very convenient and clean. Comfortable bed."

Reviewed on Oct 5, 2025

Hyatt Regency Orlando International Airport
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $156 total per night from Nov 5 to Nov 6
$156 total
Nov 5 - Nov 6
Total with taxes and fees
8.8/10 Excellent! (5,365 reviews)
"Rooms need to be cleaned better."

Reviewed on Oct 9, 2025

Universal's Cabana Bay Beach Resort
DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd, Orlando, FL
Fully refundable
$81 nightly
The price is $91 total per night from Nov 2 to Nov 3
$91 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (6,736 reviews)
"Yes"

Reviewed on Oct 8, 2025

DoubleTree by Hilton at the Entrance to Universal Orlando
See all 5,357 properties in Longwood
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.

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 $247 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.

Explore a world of travel with Expedia

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