Longwood Vacation Packages 2026 from $316

Longwood flight + hotel vacation packages

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

Westgate Town Center Resort

Save 100% on your flight

$316

per person

Apr 13 - Apr 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.

Residence Inn by Marriott Daytona Beach Oceanfront

$1,038

per person

Feb 26 - Mar 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free buffet breakfast each morning.

Westgate Cocoa Beach Resort

$1,224

per person

Mar 1 - Mar 7

found 7 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Free water park access and an outdoor pool are featured at this smoke-free condo resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site.

Westgate Palace Hotel / Universal / I-Drive

International Drive District

Save 100% on your flight

$606

per person

Apr 15 - Apr 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This resort features an outdoor pool, a gym, and a restaurant. Bring the family and enjoy the children's pool, free theme park shuttle, and kid-friendly dining. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.

Westgate Blue Tree Resort in Lake Buena Vista

Save 100% on your flight

$404

per person

Mar 29 - Apr 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool and a gym. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the hot tub and perks like free self parking.

Top Longwood hotels deals

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Free Cancellation

$113 nightly

$127 total

Jan 28 - Jan 29

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Pool

Hot Tub

Rosen Inn at Pointe Orlando

9000 International Drive Orlando FL

Free Cancellation

Reserve now, pay when you stay

$75 nightly

$85 total

Jan 27 - Jan 28

Total with taxes and fees

This hotel features 3 outdoor pools, a gym, and a restaurant. Bring the family and enjoy the free theme park shuttle, playground, and kid-friendly dining. Enjoy a meal in one of the 2 coffee shops/cafes and perks like free WiFi.

Pool

Pet friendly

Orlando International Drive North Hotel

5859 American Way Orlando FL

Free Cancellation

Reserve now, pay when you stay

$74 nightly

$84 total

Jan 29 - Jan 30

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. There's fun for all ages with a theme park shuttle and a playground. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking.

Pool

Breakfast included

Wyndham I-Drive Avanti Resort & Conference Center

6515 International Drive Orlando FL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$100 total

Jan 25 - Jan 26

Total with taxes and fees

This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the outdoor pool and perks like free self parking.

Pool

Hot Tub

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$150 total

Jan 25 - Jan 26

Total with taxes and fees

This smoke-free hotel features 2 restaurants, 2 outdoor pools, and 2 hot tubs. There's fun for all ages with a lazy river and a bowling alley, and families will appreciate the onsite laundry facilities. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and a theme park shuttle.

Pool

Hot Tub

DoubleTree by Hilton Hotel Orlando at SeaWorld

10100 International Drive Orlando FL

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$107 total

Feb 22 - Feb 23

Total with taxes and fees

This smoke-free resort features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

Pool

Pet friendly

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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.

Popular places to visit

Boardwalk at Big Tree nature park in Longwood, a suburb of Orlando in Florida

Big Tree Park

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.

Frequently asked questions

How much are vacation packages to Longwood?

You can pick up a great hotel and flight bundle for as low as $316. With one of our Travelocity vacation packages, a stay in Longwood has never been more tempting! Save your time and cash and then get a head start on packing those bags.

Where can I get the best vacation package deals for Longwood?

You can lock in sensational Longwood package deals with Travelocity. Pick and choose from as many as 400 airlines and 1,000,000 worldwide properties and turn your travel dreams into reality.

Why should I purchase my Longwood vacation package via Travelocity?

We offer 24/7 support, exceptional service and a Price Match Guarantee. Life is all about the journey — and we have enticing destinations for you to journey to all over the world. Explore with us and your wallet will thank you for it.

Can I save money on my Longwood car rental if I combine it with my hotel or flight?

Absolutely — bundle your hotel, car and flight into a Longwood vacation package and you can save a handsome sum. With so many places to explore in the Longwood area, having your own set of wheels will come in handy. Once you've settled into the driver's seat, turn up the stereo and cruise toward Daytona International Speedway, a well-known attraction about 35 mi from Longwood.

Which airport is best for Longwood?

Many choose to fly into Orlando Intl. Airport (MCO), 19 mi south of downtown Longwood. Others prefer Daytona Beach Intl. Airport (DAB) (35 mi away from central Longwood) or Orlando Sanford Intl. Airport (SFB) (8 mi away from central Longwood).

What is there to do in Longwood?

You'll sense a certain magic as you stroll through the streets of Longwood. Alaqua Country Club and The Legacy at Alaqua Lakes are just a couple of renowned sights that entice visitors to this wonderful city, so put them at the top of your must-see list.

Where should I stay when visiting Longwood?

Many people stay at the Sun-filled oasis with furnished patio, private pool, & fire pit - dog-friendly. It's an excellent base for your Longwood getaway.