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.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,019, price is now CA $585 per person
CA $585
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.2/10 Very good! (2,105 reviews)
At a regular hotel, housekeeping comes every day to clean your room. But not here. They don't provide any housekeeping service unless you stay for more than two weeks, and even then, they only come once. Despite providing absolutely no cleaning service, they still charge a $35 daily resort fee. If I had known this beforehand, I would never have stayed at this place. You have no idea how frustrating and exhausting it is to stay for an entire week without having your room cleaned even once. I've stayed at many hotels in my life, but I have never experienced anything like this. This has been one of the worst hotel experiences I've ever had.

Reviewed on Nov 6, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $2,890, price is now CA $1,516 per person
CA $1,516
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,072, price is now CA $597 per person
CA $597
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.2/10 Very good! (2,033 reviews)

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was CA $1,702, price is now CA $966 per person
CA $966
per person
Jan 24 - Jan 28
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.6/10 Excellent! (572 reviews)
Great place!

Reviewed on Nov 2, 2026

Evermore Orlando Resort

Evermore Orlando Resort

4 out of 5
Save 100% on your flight
Price was CA $3,927, price is now CA $2,370 per person
CA $2,370
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
9.6/10 Exceptional! (840 reviews)

Ready to book your vacation to Longwood?

 

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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
The price is CA $342 per night from Dec 7 to Dec 8
CA $342
CA $385 total
Dec 7 - Dec 8
includes taxes & fees
9.4/10 Exceptional! (4,608 reviews)
"overnight at airport. great choice"

Reviewed on Nov 7, 2026

Hyatt Regency Orlando International Airport
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
9500 Turkey Lake Rd Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Dec 8 to Dec 9
CA $121
CA $184 total
Dec 8 - Dec 9
includes taxes & fees
Westgate Lakes Resort & Spa Universal Studios Area
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
The price is CA $131 per night from Nov 18 to Nov 19
CA $131
CA $147 total
Nov 18 - Nov 19
includes taxes & fees
8.6/10 Excellent! (7,184 reviews)
"Great location and very helpful staff. The rooms are a little dated but for the price it was definitely worth it. Would definitely stay again!"

Reviewed on Nov 7, 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
See all 6,173 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.
See properties

What to do in Longwood

Barn Day for Little Cowboys and Cowgirls

Barn Day for Little Cowboys and Cowgirls

CA $7
per adult
Barn Day for Little Cowboys and Cowgirls
Simulated Shooting Range

Bill Drill: All-Ages Tactical Adventure in Orlando

CA $140
per adult
100% of travellers recommend
Bill Drill: All-Ages Tactical Adventure in Orlando
Orlando Science Center General Admission Ticket

Orlando Science Center General Admission Ticket

CA $41
per adult
80% of travellers recommend
Orlando Science Center General Admission Ticket
See all activities in Longwood

Frequently asked questions

How much does a Longwood vacation package cost?
You'll find cheap prices from CA $585 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.