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A greenhouse with hanging flower baskets and ivy-covered walls.

Longwood Vacations from $255

Book a Hotel + Flight or Car together to unlock savings

The Latest Longwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Restaurant
    Oct 6 - Oct 11

    Westgate Towers Resort + Flight

    Kissimmee
    5 nights
    3.5 star property
    8.6/10 - Excellent (1,003 reviews)
    "They put us in the old tower...pictures are not the same....you may want to confirm that you will be staying in the main area not away from all the amenities...."
    Reviewed July 20, 2026
    Roundtrip • New York (EWR) - Orlando (MCO)
    EWR - MCO • Nonstop MCO - EWR • Nonstop
    Save 100% on your flight
    $575
    $255
    per traveler
    found 1 day ago
    Westgate Towers Resort
  • In-room safe, laptop workspace, blackout drapes, iron/ironing board
    Oct 6 - Oct 11

    Palazzo Lakeside Hotel + Flight

    Kissimmee
    5 nights
    3.0 star property
    8.4/10 - Very Good (5,241 reviews)
    "Breakfast was just okay"
    Reviewed July 21, 2026
    Roundtrip • New York (EWR) - Orlando (MCO)
    EWR - MCO • Nonstop MCO - EWR • Nonstop
    $1,109
    $259
    per traveler
    found 1 day ago
    Palazzo Lakeside Hotel
  • Terrace/patio
    Oct 6 - Oct 11

    Westgate Palace Hotel / Universal / I-Drive + Flight

    International Drive District
    5 nights
    4.0 star property
    9.0/10 - Wonderful (1,293 reviews)
    "Located in a central location that is very close to most theme parks. Staff was friendly, the resort was very clean and comfortable. Highly recommended!"
    Reviewed July 20, 2026
    Roundtrip • New York (EWR) - Orlando (MCO)
    EWR - MCO • Nonstop MCO - EWR • Nonstop
    $944
    $367
    per traveler
    found 1 day ago
    Westgate Palace Hotel / Universal / I-Drive
  • Aerial view
    Sep 3 - Sep 9

    Westgate Vacation Villas Resort + Flight

    Kissimmee
    6 nights
    4.0 star property
    8.2/10 - Very Good (2,008 reviews)
    Roundtrip • New York (EWR) - Orlando (MCO)
    EWR - MCO • Nonstop MCO - EWR • Nonstop
    Save 100% on your flight
    $681
    $311
    per traveler
    found 1 day ago
    Westgate Vacation Villas Resort
  • Water park
    Oct 6 - Oct 11

    Westgate Lakes Resort & Spa Universal Studios Area + Flight

    Orlando
    5 nights
    4.0 star property
    8.4/10 - Very Good (6,731 reviews)
    "Water park is alot smaller than the pictures. Discount for the park was over price for the size."
    Reviewed July 20, 2026
    Roundtrip • New York (EWR) - Orlando (MCO)
    EWR - MCO • Nonstop MCO - EWR • Nonstop
    Save 100% on your flight
    $668
    $319
    per traveler
    found 1 day ago
    Westgate Lakes Resort & Spa Universal Studios Area

Discover the most popular places to visit in Longwood

Big Tree Park

6.0/10 (1 review)
Walk among ancient cypress trees, including 2,000-year-old 'Lady Liberty' on a serene boardwalk through a natural swamp. The park honors 'The Senator,' once a 3,500-year-old giant, with a memorial.

What to do in Longwood

Barn Day for Little Cowboys and Cowgirls

Barn Day for Little Cowboys and Cowgirls

$8
per adult
0% of travelers recommend
Barn Day for Little Cowboys and Cowgirls
See all activities in Longwood

Longwood Hotel Deals

Lobby

Hyatt Place Lake Mary/Orlando North

Hyatt Place Lake Mary/Orlando North
3.0 star property
4 mi from Longwood
8.8 out of 10, Excellent, (1,257 reviews)
"The staff were exceptionally helpful and the room was spacious and clean. We enjoyed the breakfast and pool. We would definitely stay here again."
$92 nightly
The price is $105
Jul 26 - Jul 27
Total with taxes and fees
Hyatt Place Lake Mary/Orlando North
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.
See all properties in Longwood

Frequently Asked Questions

How much does a Longwood vacation package cost?

You'll find cheap prices from $255 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.

Book with confidence

Things to do in and around Longwood

Longwood, Florida, offers a perfect blend of family-friendly outdoor activities and urban experiences. Visitors can enjoy beautiful resorts, recreational areas, and golf courses. Don't miss the chance to explore the stunning Longwood Gardens, take scenic walking trails, or plan personalized vacation itineraries. Be sure to check for admission tickets and day tours to make the most of your time in this charming city.

Shopping

In Longwood, you can visit Altamonte Mall, just 3 miles away, offering a vibrant shopping atmosphere with entertainment options. The Lake Mary Farmer's Market, located 4 miles away, features local goods in a bustling setting. If you're up for a drive, check out All Fired Up, 8 miles away, for unique gifts.

Recreation

Kelly Park, located 11 miles from Longwood, offers a tranquil environment perfect for relaxation amidst nature. The Seminole County Sports Complex, 8 miles away, provides a variety of activities in a serene setting. For golf enthusiasts, the Casselberry Golf Club, just 3 miles away, combines sport with beautiful outdoor scenery.

Adventure

Experience thrilling rock climbing at Aiguille Rock Climbing Center, where adventure awaits in Longwood. For karting enthusiasts, Lil 500 Go-Karts offers an exhilarating ride only 4 miles away. Enjoy family-friendly fun at Boardwalk Bowl Entertainment Center, located 11 miles away, featuring arcade games and more excitement.

Nightlife

Longwood, Florida offers a laid-back nightlife atmosphere with options like the local pub for casual drinks or the nearby lounge for a more vibrant scene. Enjoy live music, delicious dining, and friendly gatherings, perfect for an entertaining evening out with friends or family.

Find the best attractions near Longwood

Longwood, Florida, is perfect for family-friendly vacations, offering a mix of outdoor and city experiences. Explore popular attractions like urban parks, serene lakes, and art museums. Don’t miss the renowned Longwood Gardens, where you can purchase tickets for a memorable experience. Whether you're looking for venues or planning a trip to Longwood Gardens, there's plenty to keep you entertained and engaged during your visit.

  • Wekiwa Springs State Park: Experience the beauty of nature at Wekiwa Springs State Park, located 8 miles from Longwood. This park offers a thrilling outdoor adventure with opportunities for swimming, canoeing, and hiking amidst lush landscapes and scenic waterways.
  • Boombah-Soldiers Creek Park: Just 2 miles from Longwood, Boombah-Soldiers Creek Park is perfect for family outings. Enjoy playgrounds, sports facilities, and picnic areas in an inviting urban park that combines outdoor fun with vibrant city energy.
  • Rollins College: Situated 8 miles away, Rollins College is a stunning campus known for its beautiful architecture and serene lakeside setting. Explore its rich history and vibrant academic vibe while strolling through the picturesque grounds.

Best time to go to Longwood

The best time to visit Longwood can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Longwood falls in August, when visitor numbers are average and weather is mostly sunny with moderate rain. The coolest average temperature in Longwood falls in January, visitor numbers are average and weather is mostly sunny with light rain.

Tips to save on your trip to Longwood

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Longwood.
  • Consider traveling during the off-peak season (typically August to September and November) for more affordable package holidays to Longwood.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.