Longwood Vacation Packages 2026 from $509

Longwood flight + hotel vacation packages

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

The Delaney Hotel

South Orange

$509

per person

Jan 17 - Jan 22

found 1 day ago

Roundtrip 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.

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

Save 100% on your flight

$523

per person

Jan 29 - Feb 5

found 3 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.

Ocean Landings Resort and Racquet

Save 100% on your flight

$704

per person

Jan 13 - Jan 20

found 10 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This smoke-free hotel features 2 outdoor pools, a hot tub, and a restaurant. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A coffee shop, laundry facilities, and barbecue grills are also on offer.

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$747

per person

Jan 13 - Jan 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Free water park access, 4 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. You'll appreciate the hot tub, poolside bar, and snack bar/deli.

Oceanique Resort

Save 100% on your flight

$914

per person

Jan 13 - Jan 20

found 10 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.

Top Longwood hotels deals

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

Free Cancellation

Reserve now, pay when you stay

$215 nightly

$242 total

Nov 23 - Nov 24

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

$116 nightly

$131 total

Nov 15 - Nov 16

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

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Free Cancellation

$93 nightly

$104 total

Nov 23 - Nov 24

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

$173 nightly

$195 total

Nov 30 - Dec 1

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

Coco Key Hotel & Water Park Resort

7400 International Dr Orlando FL

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$135 total

Dec 7 - Dec 8

Total with taxes and fees

Free water park access, 5 restaurants, and 3 outdoor pools are all featured at this traditional hotel. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Unwind with a drink at one of the 2 poolside bars and enjoy perks like a free 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

$129 nightly

$145 total

Dec 13 - Dec 14

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

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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 $509. 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.