Winter Park Vacation Packages 2026 from $277

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

$277

per person

Nov 13 - Nov 18

found 1 day ago

Roundtrip flight included

San Juan (SJU) 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.

Seasons Florida Resort

Save 100% on your flight

$310

per person

Dec 6 - Dec 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 Cocoa Beach Resort

Save 100% on your flight

$693

per person

Nov 18 - Nov 22

found 21 hours ago

Roundtrip flight included

Minneapolis (MSP) to Orlando (MCO)

Free water park access and an outdoor pool are featured at this traditional aparthotel. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$367

per person

Nov 19 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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 mini golf and a children's pool, and barbecue grills are available on site. Enjoy the 7 outdoor pools and get free valet parking.

Disney's Animal Kingdom Lodge

Bay Lake

Save 100% on your flight

$1,039

per person

Nov 28 - Dec 1

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. There's fun for all ages with a children's club and a theme park shuttle, and families will appreciate the onsite laundry facilities. Traveling on business? Take advantage of the express check-in, express check-out, and valet parking.

Top Winter Park hotels deals

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

Free Cancellation

Reserve now, pay when you stay

$209 nightly

$235 total

Sep 14 - Sep 15

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

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr Orlando FL

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$147 total

Sep 21 - Sep 22

Total with taxes and fees

This smoke-free aparthotel features 3 restaurants, 6 outdoor pools, and 10 outdoor tennis courts. There's fun for all ages with a free kid's club and mini golf, and barbecue grills are available on site. Enjoy the 8 hot tubs and perks like free WiFi.

Pool

Hot Tub

Marriott's Grande Vista

5925 Avenida Vista Orlando FL

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$108 total

Oct 5 - Oct 6

Total with taxes and fees

This smoke-free aparthotel 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 the 4 outdoor pools and perks like free WiFi.

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

$119 nightly

$134 total

Sep 14 - Sep 15

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

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL

Free Cancellation

Reserve now, pay when you stay

$150 nightly

$169 total

Sep 14 - Sep 15

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 at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL

Free Cancellation

$93 nightly

$104 total

Sep 27 - Sep 28

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

Don't see what you're looking for?

See all available properties in Winter Park

View all properties

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 Winter Park attractions

A bar with wooden decor, a TV screen, and a bartender wearing a red jersey.

Full Sail University

8.4/10 (73 reviews)

Enjoy the collegiate vibe when you visit Full Sail University, during your trip to Winter Park. Discover the area's top-notch restaurants and its acclaimed theater scene.

See properties

Frequently asked questions

How much are vacation packages to Winter Park?

You can pick up a great flight and hotel bundle for a mere $277. 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.