Longwood Vacation Packages 2025/2026 from $376

Longwood flight + hotel vacation packages

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

Westgate River Ranch Resort & Rodeo

Save 100% on your flight

$376

per person

Oct 31 - Nov 3

found 13 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This smoke-free resort features free water park access, a marina, and 2 restaurants. There's fun for all ages with mini golf and a playground, and barbecue grills are available on site. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking.

Westgate Palace Hotel / Universal / I-Drive

International Drive District

$483

per person

Dec 1 - Dec 7

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 Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$431

per person

Nov 20 - Nov 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This smoke-free hotel features a full-service spa, a water park, and a marina. There's fun for all ages with a lazy river and a children's club, and barbecue grills are available on site. Enjoy the 7 outdoor pools and perks like free valet parking and a free theme park shuttle.

Westgate Cocoa Beach Resort

$683

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip flight included

Detroit (DTW) 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.

Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

Palm Valley

Save 100% on your flight

$411

per person

Nov 10 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. You'll appreciate the gym, bar/lounge, and snack bar/deli.

Top Longwood hotels deals

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$102 nightly

$115 total

Sep 14 - Sep 15

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.

Universal's Cabana Bay Beach Resort

6550 Adventure Way, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$136 nightly

$153 total

Sep 29 - Sep 30

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.

DoubleTree by Hilton Hotel Orlando at SeaWorld

10100 International Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$101 nightly

$113 total

Sep 21 - Sep 22

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.

Rosen Inn at Pointe Orlando

9000 International Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$65 nightly

$74 total

Sep 11 - Sep 12

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.

DoubleTree by Hilton Orlando Airport

5555 Hazeltine National Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$113 total

Oct 4 - Oct 5

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free WiFi and a free airport shuttle. You'll appreciate the free area shuttle, valet parking, and 24-hour business center.

Hyatt Regency Orlando

9801 International Dr, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$177 nightly

$199 total

Sep 23 - Sep 24

Total with taxes and fees

A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this luxury hotel. Bring the family and enjoy the children's pool, free theme park shuttle, and waterslide. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and an area shuttle.

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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

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 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 great live music.

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 $376. 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.