Winter Garden Vacation Packages 2025/2026 from $138

Winter Garden flight + hotel vacation packages

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

Palazzo Lakeside Hotel

Save 100% on your flight

$138

per person

Dec 7 - Dec 12

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.

Westgate Palace Hotel / Universal / I-Drive

International Drive District

$340

per person

Dec 12 - Dec 16

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Westgate Cocoa Beach Resort

$1,128

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.

Hilton Daytona Beach Oceanfront Resort

Brush - Stewarts

Save 100% on your flight

$518

per person

Dec 8 - Dec 15

found 24 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

4 restaurants, 2 outdoor pools, and 2 hot tubs are among this hotel's featured amenities. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Enjoy the 24-hour gym and visit the 2 beach bars and poolside bar for drinks.

The Delaney Hotel

South Orange

$408

per person

Dec 11 - Dec 16

found 1 day ago

Roundtrip non-stop 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

$209 nightly

$235 total

Oct 6 - Oct 7

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

$107 nightly

$120 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

$122 nightly

$138 total

Oct 14 - Oct 15

Total with taxes and fees

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

Pool

Breakfast included

Hilton Vacation Club Aqua Sol Orlando West

17777 Bali Blvd, Winter Garden, FL

Free Cancellation

Reserve now, pay when you stay

$131 nightly

$148 total

Oct 16 - Oct 17

Total with taxes and fees

This smoke-free hotel features free water park access, 2 outdoor pools, and a restaurant. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.

Pool

Hot Tub

Homewood Suites by Hilton Orlando at Flamingo Crossings

411 Flagler Ave, Winter Garden, FL

Free Cancellation

Reserve now, pay when you stay

$140 nightly

$157 total

Oct 14 - Oct 15

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

Hyatt Regency Orlando International Airport

9300 Jeff Fuqua Boulevard, Orlando, FL

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$201 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

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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

Flamingo Crossings Town Center

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.

Orange County National Golf Club

Enjoy a round of golf in Winter Garden at Orange County National Golf Club. Amble around this family-friendly area's lakeside or experience its entertainment choices.

Disney's Palm Golf Course

Enjoy a round of golf in Winter Garden at Disney's Palm Golf Course. Discover the top-notch restaurants and entertainment choices in this family-friendly area.

Frequently asked questions

How much are vacation packages to Winter Garden?

Packages, which include hotels and flights in Winter Garden, start at just $138. 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.