Deals on vacations and trips to Winter Garden

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Winter Garden flight + hotel vacation packages

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Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Save 100% on your flight
Price was $793, price is now $438 per person
$438
per person
Dec 5 - Dec 11
found 11 hours 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.
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $1,406, price is now $588 per person
$588
per person
Dec 22 - Dec 27
found 21 hours 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.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was $4,712, price is now $2,103 per person
$2,103
per person
Dec 28 - Jan 2
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.
Disney's Animal Kingdom Lodge

Disney's Animal Kingdom Lodge

4.5 out of 5
Bay Lake
Save 100% on your flight
Price was $2,044, price is now $1,142 per person
$1,142
per person
Dec 15 - Dec 18
found 1 day 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.
The Resort on Cocoa Beach

The Resort on Cocoa Beach

3.5 out of 5
Price was $848, price is now $499 per person
$499
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
This aparthotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the gym and perks like free self parking and free WiFi. There's a hot tub on site, and barbecue grills and a virtual front desk are also offered.

Top Winter Garden hotels deals

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Free Cancellation
Reserve now, pay when you stay
$228 nightly
The price is $257 total per night
$257 total
Oct 24 - Oct 25
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

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

3 out of 5
631 FLAGLER AVE Winter Garden FL
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $85 total per night
$85 total
Nov 11 - Nov 12
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

Home2 Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
341 Flagler Ave Winter Garden FL
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $110 total per night
$110 total
Nov 2 - Nov 3
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

Homewood Suites by Hilton Orlando at Flamingo Crossings

3 out of 5
411 Flagler Ave Winter Garden FL
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $142 total per night
$142 total
Nov 22 - Nov 23
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

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

3 out of 5
2111 FLAGLER AVE Winter Garden FL
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $109 total per night
$109 total
Nov 11 - Nov 12
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
Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West

4 out of 5
17777 Bali Blvd Winter Garden FL
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $134 total per night
$134 total
Nov 16 - Nov 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 a free kid's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 24-hour gym 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.

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 $438. 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.

Photos of local treasures

Browse Winter Garden vacation photos for more inspiration

A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.
A sunset over the ocean with silhouettes of two people on a dock.
A sandy beach with a calm blue sea and distant shoreline.
A sign for Downtown Intergarden with an American flag, Farmers Market on Saturdays, and a Concert Series on Fridays.
A sunset over a calm lake with a pier and trees.

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