Longwood Vacation Packages 2026 from $279

Longwood flight + hotel vacation packages

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

Westgate Vacation Villas Resort

Save 100% on your flight

$279

per person

Nov 3 - Nov 7

found 21 hours ago

Roundtrip non-stop 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 a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.

Westgate Towers Resort

Save 100% on your flight

$352

per person

Oct 29 - Nov 5

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Orlando (MCO)

2 outdoor pools, 2 hot tubs, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Westgate Palace Hotel / Universal / I-Drive

International Drive District

Save 100% on your flight

$654

per person

Nov 4 - Nov 9

found 5 hours 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 River Ranch Resort & Rodeo

Save 100% on your flight

$364

per person

Oct 2 - Oct 4

found 1 day ago

Roundtrip flight included

San Juan (SJU) 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.

The Delaney Hotel

South Orange

Save 100% on your flight

$452

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a terrace, and a snack bar/deli are also offered.

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

$71 nightly

$80 total

Sep 1 - Sep 2

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

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL

Free Cancellation

Reserve now, pay when you stay

$150 nightly

$169 total

Aug 27 - Aug 28

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

Universal's Endless Summer Resort - Dockside Inn and Suites

7125 Universal Boulevard Orlando FL

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$138 total

Aug 27 - Aug 28

Total with taxes and fees

This smoke-free hotel features 2 outdoor pools, a gym, and a restaurant. Bring the family and enjoy the children's pool, early theme park entry, and arcade/game room. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.

Pool

Free WiFi

Wyndham I-Drive Avanti Resort & Conference Center

6515 International Drive Orlando FL

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$92 total

Aug 27 - Aug 28

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

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$201 total

Sep 7 - Sep 8

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Pool

Free WiFi

Westgate Lakes Resort & Spa Universal Studios Area

9500 Turkey Lake Rd Orlando FL

$115 nightly

$125 total

Aug 31 - Sep 1

Total with taxes and fees

This smoke-free hotel features a full-service spa, a water park, and a marina. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the 7 outdoor pools and get free valet parking.

Pool

Hot Tub

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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.

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

Frequently asked questions

How much are vacation packages to Longwood?

You can pick up a great hotel and flight bundle for as low as $279. 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.