Winter Garden Vacation Packages 2025/2026 from $313

Winter Garden flight + hotel vacation packages

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

Westgate Town Center Resort

$313

per person

Jan 27 - Feb 3

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 mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.

Florida Hotel & Conference Center in the Florida Mall

$420

per person

Jan 23 - Jan 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This traditional aparthotel includes 3 restaurants, an outdoor pool, and a gym. Bring the family and enjoy the free theme park shuttle and kid-friendly dining. Enjoy the hot tub and perks like free WiFi.

The Delaney Hotel

South Orange

$346

per person

Jan 25 - Jan 29

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.

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

Vilano Beach

$512

per person

Feb 1 - Feb 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

The private beach and full-service spa are among the highlights at this hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. Enjoy the outdoor pool and free perks like buffet breakfast and WiFi in public areas.

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

$750

per person

Jan 23 - Jan 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Free water park access, 4 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. You'll appreciate the hot tub, poolside bar, and snack bar/deli.

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

$159 nightly

$179 total

Nov 20 - Nov 21

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.

Home2 Suites by Hilton Orlando at Flamingo Crossings

341 Flagler Ave Winter Garden FL

Free Cancellation

Reserve now, pay when you stay

$103 nightly

$116 total

Nov 30 - Dec 1

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

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

$112 nightly

$126 total

Dec 9 - Dec 10

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.

Homewood Suites by Hilton Orlando at Flamingo Crossings

411 Flagler Ave Winter Garden FL

$111 nightly

$125 total

Dec 1 - Dec 2

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.

Hilton Vacation Club Aqua Sol Orlando West

17777 Bali Blvd Winter Garden FL

$131 nightly

$148 total

Nov 24 - Nov 25

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.

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$150 total

Nov 20 - Nov 21

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.

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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

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.

Disney's Magnolia Golf Course

4/5(6 reviews)

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

Disney's Palm Golf Course

5/5(1 review)

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 $313. 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.