Winter Park Vacation Packages 2026 from $208

Winter Park flight + hotel vacation packages

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

The Shores Resort & Spa

$208

per person

Feb 1 - Feb 6

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and an arcade/game room, and complimentary bicycles are available on site. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.

Palazzo Lakeside Hotel

$344

per person

Mar 13 - Mar 17

found 1 day ago

Roundtrip 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.

Seasons Florida Resort

$298

per person

Feb 8 - Feb 12

found 1 day ago

Roundtrip 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.

Westgate Vacation Villas Resort

$383

per person

Mar 6 - Mar 9

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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 Cocoa Beach Resort

$1,227

per person

Feb 22 - Feb 28

found 9 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.

Top Winter Park hotels deals

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$150 total

Jan 6 - Jan 7

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

Wyndham I-Drive Avanti Resort & Conference Center

6515 International Drive Orlando FL

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$90 total

Jan 5 - Jan 6

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

Rosen Inn at Pointe Orlando

9000 International Drive Orlando FL

Free Cancellation

Reserve now, pay when you stay

$72 nightly

$82 total

Jan 25 - Jan 26

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

Avanti International Resort

8738 International Dr Orlando FL

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$109 total

Feb 1 - Feb 2

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Bring the family and enjoy the children's pool, free theme park shuttle, and arcade/game room. Enjoy the gym and perks like free WiFi.

Pool

Hot Tub

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Free Cancellation

$89 nightly

$101 total

Jan 15 - Jan 16

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

DoubleTree by Hilton Hotel Orlando at SeaWorld

10100 International Drive Orlando FL

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$119 total

Jan 30 - Jan 31

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

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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

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Universal Studios Florida

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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

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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 $208. 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.