Winter Park Vacation Packages 2025/2026 from $268

Winter Park flight + hotel vacation packages

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

Westgate Towers Resort

Save 100% on your flight

$268

per person

Oct 17 - Oct 22

found 24 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

This hotel features an outdoor pool and a gym. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the hot tub and perks like free self parking.

Westgate Lakes Resort & Spa Universal Studios Area

$430

per person

Oct 19 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) 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.

ette hotel

$785

per person

Oct 19 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) to Orlando (MCO)

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free valet parking. Enjoy the gym and perks like free self parking.

Seasons Florida Resort

Save 100% on your flight

$328

per person

Oct 19 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Denver (DEN) 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.

Westgate Palace Hotel / Universal / I-Drive

International Drive District

Save 100% on your flight

$465

per person

Oct 9 - Oct 13

found 1 day ago

Roundtrip flight included

Denver (DEN) 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.

Top Winter Park hotels deals

Marriott's Grande Vista

5925 Avenida Vista, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$98 total

Sep 25 - Sep 26

Total with taxes and fees

This eco-certified hotel features a golf course, a full-service spa, and 3 restaurants. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy a meal in one of the 2 coffee shops/cafes and perks like free WiFi.

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 9 - Sep 10

Total with taxes and fees

This eco-certified 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

$138 nightly

$155 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.

Pool

Hot Tub

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

12401 International Dr, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$95 total

Oct 1 - Oct 2

Total with taxes and fees

This smoke-free hotel features 2 restaurants, 5 outdoor pools, and 2 outdoor tennis courts. Bring the family and enjoy the children's club, children's pool, and waterslide. Enjoy the 4 hot tubs and perks like free WiFi.

Pool

Hot Tub

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 7 - Sep 8

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

$65 nightly

$74 total

Sep 5 - Sep 6

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

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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

Walt Disney World® Resort

Have a fun-filled day at Walt Disney World® Resort and find out why this is a popular theme park in Lake Buena Vista. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Universal Studios Florida

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Orlando showing street scenes, a city and rides

Universal Orlando Resort

Have a fun-filled day at Universal Orlando Resort and see why people love this theme park in Orlando. Check out the shops and top-notch restaurants in this family-friendly area.

Frequently asked questions

How much are vacation packages to Winter Park?

You can pick up a great flight and hotel bundle for a mere $268. With one of our Travelocity vacation packages, a getaway in Winter Park has never looked so good! Save some time and money and then get a start on packing those bags.

How long should my Winter Park vacation be?

Most travelers choose to spend about 2 nights in Winter Park, but how long you stay is your call. If you'd like to discover all the incredible things this destination has waiting for you, why not hang around a while longer?

Where can I get the best vacation package deals for Winter Park?

There are fantastic Winter Park package deals to snap up with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties around the globe? Keep that in mind when you're ready to cross another place off your bucket list.

Why should I purchase my Winter Park vacation package via Travelocity?

With first-rate service, 24/7 customer support and some of the most gorgeous getaways money can buy, you'll never roam alone. And if you find a cheaper price, we'll match it. That's our Price Match Guarantee.

Will I save money on my Winter Park car rental if I book it with a hotel or flight?

With a Winter Park vacation package, you can bundle your car, flight and hotel bookings and save a tidy sum. When you're ready to uncover the best of this wonderful region, why not make tracks to Daytona International Speedway? This top sight is 45 mi from Winter Park. With your own rental car, you'll be there soon enough.

Which airport is best for Winter Park?

Many travelers fly into Orlando Intl. Airport (MCO), 12 mi south of downtown Winter Park. Others prefer Daytona Beach Intl. Airport (DAB) (45 mi away from central Winter Park) or Orlando Sanford Intl. Airport (SFB) (13 mi away from central Winter Park).

What is there to do in Winter Park?

While venturing off the beaten track is rewarding, you really shouldn't miss the big sights that make a place famous. Full Sail University and Rollins College are a couple of them in Winter Park.

Where should I stay when visiting Winter Park?

The Hilton Garden Inn Winter Park is popular with many travelers. Book as soon as possible before it's too late.