Winter Garden Vacation Packages 2026 from $333

Winter Garden flight + hotel vacation packages

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

Seasons Florida Resort

Save 100% on your flight

$333

per person

Sep 30 - Oct 6

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 Palace Hotel / Universal / I-Drive

International Drive District

$414

per person

Sep 6 - Sep 11

found 2 hours ago

Roundtrip non-stop 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 Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$433

per person

Sep 30 - Oct 6

found 1 day ago

Roundtrip 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.

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

$930

per person

Sep 30 - Oct 6

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.

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

Save 100% on your flight

$349

per person

Oct 18 - Oct 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.

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

$218 nightly

$245 total

Aug 4 - Aug 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

$74 nightly

$83 total

Aug 17 - Aug 18

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

Aug 9 - Aug 10

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

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

13279 Hartzog Road Winter Garden FL

Free Cancellation

Reserve now, pay when you stay

$95 nightly

$107 total

Aug 23 - Aug 24

Total with taxes and fees

Pool

Hot Tub

Hilton Vacation Club Aqua Sol Orlando West

17777 Bali Blvd Winter Garden FL

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$134 total

Aug 27 - Aug 28

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 24-hour gym and perks like 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

$106 nightly

$119 total

Aug 9 - Aug 10

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

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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 walkable 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 $333. 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.