Deals on vacations and trips to Winter Garden

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Winter Garden flight + hotel vacation packages

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

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $586, price is now $277 per person
$277
per person
Nov 13 - Nov 18
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
2 outdoor pools, 2 hot tubs, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
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 $638, price is now $343 per person
$343
per person
Dec 4 - Dec 8
found 18 hours ago
Roundtrip flight included
Philadelphia (PHL) 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 Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,256, price is now $693 per person
$693
per person
Nov 18 - Nov 22
found 23 hours 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.
Disney's Animal Kingdom Lodge

Disney's Animal Kingdom Lodge

4.5 out of 5
Bay Lake
Save 100% on your flight
Price was $1,863, price is now $1,039 per person
$1,039
per person
Nov 28 - Dec 1
found 18 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 Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $658, price is now $367 per person
$367
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop 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.

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
$238 nightly
The price is $268 total per night
$268 total
Oct 13 - Oct 14
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
$89 nightly
The price is $100 total per night
$100 total
Sep 29 - Sep 30
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
$90 nightly
The price is $101 total per night
$101 total
Sep 27 - Sep 28
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
$130 nightly
The price is $147 total per night
$147 total
Sep 22 - Sep 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
Sep 28 - Sep 29
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

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard Orlando FL
Free Cancellation
Reserve now, pay when you stay
$209 nightly
The price is $235 total per night
$235 total
Sep 14 - Sep 15
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 $277. 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 wooden pier extending over calm water, reflecting a sunset sky.

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