Winter Garden Vacation Packages 2026 from $450

Winter Garden flight + hotel vacation packages

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

Westgate Vacation Villas Resort

Save 100% on your flight

$450

per person

Nov 5 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Disney's Animal Kingdom Lodge

Bay Lake

Save 100% on your flight

$1,241

per person

Nov 27 - Dec 1

found 11 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.

Westgate Cocoa Beach Resort

Save 100% on your flight

$885

per person

Nov 15 - Nov 20

found 1 day 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.

Seasons Florida Resort

$766

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

A free theme park shuttle and free self parking are featured at this hotel, along with an outdoor pool. WiFi in public areas is free. Laundry facilities are provided for your convenience.

The Delaney Hotel

South Orange

Save 100% on your flight

$1,395

per person

Dec 26 - Jan 2

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Top Winter Garden hotels deals

The Grove Resort & Water Park Orlando

14501 Grove Resort Avenue Winter Garden FL

Free Cancellation

Reserve now, pay when you stay

$219 nightly

$246 total

Nov 4 - Nov 5

Total with taxes and fees

Free water park access, 3 restaurants, and 6 outdoor pools are all featured at this resort. Bring the family and enjoy the lazy river, children's club, and mini golf. Enjoy the 2 hot tubs and perks like free WiFi.

Pool

Hot Tub

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

631 FLAGLER AVE Winter Garden FL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$100 total

Oct 26 - Oct 27

Total with taxes and fees

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free buffet breakfast and a free theme park shuttle.

Pool

Breakfast included

Home2 Suites by Hilton Orlando at Flamingo Crossings

341 Flagler Ave Winter Garden FL

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$110 total

Oct 25 - Oct 26

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and a theme park shuttle.

Pool

Breakfast included

Homewood Suites by Hilton Orlando at Flamingo Crossings

411 Flagler Ave Winter Garden FL

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$147 total

Oct 18 - Oct 19

Total with taxes and fees

The hotel's outdoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Enjoy a meal from the restaurant and perks like free buffet breakfast and a free theme park shuttle. Self parking, a 24-hour business center, and a coffee shop are also offered.

Pool

Breakfast included

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

2111 FLAGLER AVE Winter Garden FL

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$118 total

Oct 26 - Oct 27

Total with taxes and fees

The hotel's outdoor pool, 24-hour gym, and 2 bars/lounges are among the featured amenities. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the poolside bar and enjoy perks like free buffet breakfast and a free theme park shuttle.

Pool

Breakfast included

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard Orlando FL

Free Cancellation

Reserve now, pay when you stay

$220 nightly

$248 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. 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

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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.

Stay near popular Winter Garden attractions

Flamingo Crossings Town Center

8.6/10 (131 reviews)

You can do some window-shopping at Flamingo Crossings Town Center during your visit to Winter Garden. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

See properties

Frequently asked questions

How much are vacation packages to Winter Garden?

Packages, which include hotels and flights in Winter Garden, start at just $450. Turn your daydreams into reality and begin your booking with Travelocity today.

How long should my Winter Garden vacation be?

Many visitors pack their suitcase and explore the sights of Winter Garden for about 4 nights. That's a great guide, but don't feel restricted by it. Whether you only stay for a day or two to see the famous sights or hang around to uncover hidden gems, an amazing escape awaits.

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

No matter what you enjoy doing, Travelocity can help you find an unbeatable Winter Garden package deal. The only thing you need to do is mix and match from our 400 airlines and 1,000,000 properties worldwide.

Why should I purchase my Winter Garden vacation bundle with Travelocity?

From enticing destinations to one-of-a-kind experiences, we have everything you need to appease your wanderlust. Our 24/7 customer care will also ensure you're taken care of during your vacation. And don't worry if you notice a cheaper price on your reservation, we'll match it. That's our Price Match Guarantee.

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

Absolutely — combine your hotel, car and flight into a Winter Garden vacation package and you'll save tons. With so much to see in Winter Garden, that set of wheels will make exploring easy. Once you've slid into the driver's seat, hit the wide open road and head toward Daytona International Speedway, a must-see attraction about 55 mi from Winter Garden.

Which airport is best for Winter Garden?

Orlando Intl. Airport (MCO) is one of the top airports for Winter Garden. It's roughly 19 mi southeast of the buzzing city center. Other options open to you are Daytona Beach Intl. Airport (DAB) (55 mi away from central Winter Garden) and Orlando Sanford Intl. Airport (SFB) (25 mi away from central Winter Garden).

What is there to do in Winter Garden?

You'll notice an undeniable magic as you wander the streets of Winter Garden. Orange County National Golf Club and Surfari Water Park are just two famous sights that entice visitors to this wonderful city, so put them on your must-see list.

Where should I stay when visiting Winter Garden?

Many people opt to check in to the Hilton Vacation Club Aqua Sol Orlando West. It's sure to be a good base for your Winter Garden getaway.