Longwood Vacation Packages
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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.
Top Longwood Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
CA $624
per person
Nov 22 - Nov 29
found 3 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9/10 Wonderful! (3,830 reviews)
Room was very clean, easy to get access over night past regular desk hours just contact them before hand. AC in the room was ice cold, beds were spacious and on the firm side. Plenty of parking, and it’s near like a 7 eleven and mini golf. I enjoyed my stay
Reviewed on Aug 31, 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
CA $1,469
per person
Nov 22 - Nov 29
found 10 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.2/10 Wonderful! (1,006 reviews)
Our family absolutely loved staying in the cottages. It was nicely updated and so much space for everyone to spread out. Although we didn’t have time to use them, the waterpark passes are a nice bonus. I’m sure we will likely stay here again when we are back in the area.
Reviewed on Aug 30, 2026
Ready to book your vacation to Longwood?
Longwood Hotel Deals
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
CA $249
CA $280 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (4,434 reviews)
"Booked this last minute after weather canceled my flight. I booked a balcony room mistakenly thinking i would have an indoor view of the airport but it was outdoor unfortunately. Very nice hotel. Room and hallways were clean and didn't smell. Only warning is the elevator is very busy in the morning ..."
Reviewed on Aug 31, 2026
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
CA $185
CA $208 total
Sep 1 - Sep 2
includes taxes & fees
Universal's Endless Summer Resort - Dockside Inn and Suites
7125 Universal Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
CA $175
CA $197 total
Sep 10 - Sep 11
includes taxes & fees
9.2/10 Wonderful! (5,667 reviews)
"Check in was chaotic. The person checking us in gave us access to the wrong room and I had to go back down (after waiting awhile to begin with) to get this straightened out). The parking was decent other than the card is hard to put against the reader from a distance and the machine says "thank you ..."
Reviewed on Aug 31, 2026
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.
Stay near popular Longwood attractions
Big Tree Park
6.0/10 (1 review)
Big Tree Park is just one of the places to see in Longwood, so why not enjoy the other things to explore during your travels? Amble around the area's lakeside or attend a sporting event.
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.
Alaqua Country Club
Enjoy a round of golf in Longwood at Alaqua Country Club. While you're in the area, stroll along the lakeside.
Lake Brantley Field House
Catch an event at Lake Brantley Field House during your trip to Longwood. Stroll along the lakeside or visit the shops while you're in the area.
Aiguille Rock Climbing Center
You can take time to visit Aiguille Rock Climbing Center during your travels to Longwood. Experience the area's great live music or attend a sporting event.
The Senator Tree
Commune with nature and explore the great outdoors at The Senator Tree during your travels in Longwood. Wander the lakeside or discover the area's sunsets.
What to do in Longwood
Bill Drill: All-Ages Tactical Adventure in Orlando
CA $137
per adult
100% of travellers recommend
St. Johns River High-Tea Cruise Tour in Sanford
CA $66
per adult
100% of travellers recommend
Rock Springs 2-Hour Glass Bottom Guided Kayak Eco Tour
CA $165
per adult
100% of travellers recommend
Frequently asked questions
How much does a Longwood vacation package cost?
You'll find cheap prices from CA $624 on Expedia for your Longwood getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Longwood costs.
What are the cheapest months to go to Longwood?
Plan your getaway for the shoulder or low season and you're likely to find cheap Longwood vacation packages. Remember that public holidays and local festivals and events can have an impact on prices, so do a little research before you go.
How many days is enough for Longwood?
The ideal length for your Longwood vacation depends on what you'd like to do. Typically, a handful of days to a week will give you plenty of time to go to all the main attractions and explore some hidden gems along the way.
Is it worth booking a vacation package to Longwood?
It's no wonder a Longwood vacation is on the must-do list of many travellers. Top attractions like Boombah-Soldiers Creek Park are just the start of things to keep you busy here.
How to find the best Longwood package deals?
Finding a cheap Longwood package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a few filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Longwood package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Longwood vacation as a package?
You can enjoy significant savings on your Longwood escape by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
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 one week before you go. Don't want to leave things to the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Longwood?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Longwood.
- Budget wisely: In addition to the price of your stay, you should factor in other expenses. These include food, flights and transportation. Also, set aside a little extra for unexpected expenses that may arise during your trip to Longwood.
- Work out your trip length: Think about how much time you'd like to spend exploring Longwood. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
- Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick a Longwood vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
