Winter Park Vacation Packages 2025/2026 from $213

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

$213

per person

Dec 6 - Dec 10

just found

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

The Delaney Hotel

South Orange

$520

per person

Dec 12 - Dec 19

found 1 day ago

Roundtrip flight included

Detroit (DTW) 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.

Westgate Cocoa Beach Resort

$1,103

per person

Nov 25 - Nov 30

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) 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.

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$501

per person

Nov 19 - Nov 25

found 1 day ago

Roundtrip flight included

Detroit (DTW) 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.

Bryan’s Spanish Cove

$485

per person

Dec 12 - Dec 19

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Orlando (MCO)

An outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and concierge services are also on offer.

Top Winter Park hotels deals

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$181 nightly

$204 total

Oct 6 - Oct 7

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

Marriott's Grande Vista

5925 Avenida Vista, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$98 total

Oct 26 - Oct 27

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

Universal's Cabana Bay Beach Resort

6550 Adventure Way, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$140 nightly

$158 total

Nov 5 - Nov 6

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 Resort Villas, Lake Buena Vista/Orlando

8800 Vistana Centre Dr, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$99 nightly

$112 total

Oct 27 - Oct 28

Total with taxes and fees

This smoke-free hotel 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

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd, Orlando, FL

Free Cancellation

$89 nightly

$100 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

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

12401 International Dr, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$98 total

Oct 26 - Oct 27

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

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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 $213. 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.