Longwood Vacation Packages 2025/2026 from $286

Longwood flight + hotel vacation packages

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

Seasons Florida Resort

$286

per person

Jan 6 - Jan 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and laundry facilities are also provided.

Hilton Orlando

International Drive District

$566

per person

Jan 6 - Jan 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

A full-service spa, 5 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Bring the family and enjoy the lazy river, children's pool, and waterslide. Traveling on business? Take advantage of the business center, express check-out, and valet parking.

Palazzo Lakeside Hotel

$290

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool, a gym, and a restaurant. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Westgate Cocoa Beach Resort

$1,408

per person

Dec 25 - Jan 1

found 2 hours ago

Roundtrip non-stop 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.

Florida Hotel & Conference Center in the Florida Mall

$482

per person

Dec 2 - Dec 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This traditional aparthotel includes 3 restaurants, an outdoor pool, and a gym. Bring the family and enjoy the free theme park shuttle and kid-friendly dining. Enjoy the hot tub and perks like free WiFi.

Top Longwood hotels deals

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$190 total

Oct 27 - Oct 28

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

Universal's Cabana Bay Beach Resort

6550 Adventure Way, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$150 total

Nov 4 - Nov 5

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

$101 nightly

$114 total

Nov 24 - Nov 25

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

Rosen Inn at Pointe Orlando

9000 International Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$72 nightly

$82 total

Nov 23 - Nov 24

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

Wyndham I-Drive Avanti Resort & Conference Center

6515 International Drive, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$90 total

Oct 27 - Oct 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

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd, Orlando, FL

Free Cancellation

$98 nightly

$110 total

Nov 2 - Nov 3

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

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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 acclaimed theater scene.

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 $286. 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.