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Winter Garden Vacation Packages

Choose two or more items and save on your trip:

Top Winter Garden Flight + Hotel Deals

CLC Regal Oaks Resort Vacation Townhomes

CLC Regal Oaks Resort Vacation Townhomes

4 out of 5
Save 100% on your flightCA $1,549

CA $1,063

per person
Jun 19 - Jun 26
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
4.2/5Very Good! (1,914 reviews)

"First and last experience, didn’t like it!! This is not a nice place to enjoy a vacation with family, need more effort in cleaning the apartments…"

Reviewed on Apr. 12, 2021

Hyatt Regency Grand Cypress

Hyatt Regency Grand Cypress

4 out of 5
CA $933

CA $768

per person
May 23 - May 27
Roundtrip non-stop flight included
Calgary (YYC) to Orlando (MCO)
4.6/5Wonderful! (2,324 reviews)

"It was a beautiful resort. Tons to do for families and children. The downfalls were the beds and bedding were very uncomfortable. The food was expensive and not very many options. Every “restaurant” had the same food. I also was not very impressed with the timely of service. Getting coffee in the morning took 10 minutes as well as to get a drink at the bar. When eating at the lake house restaurant the service was very slow.…"

Reviewed on Apr. 14, 2021

Fantasy World Resort

Fantasy World Resort

3.5 out of 5
CA $759

CA $648

per person
May 23 - May 27
Roundtrip non-stop flight included
Calgary (YYC) to Orlando (MCO)
4.2/5Very Good! (3,615 reviews)

"The water slide was good for the kids…"

Reviewed on Apr. 14, 2021

CLC Encantada Resort Vacation Townhomes

CLC Encantada Resort Vacation Townhomes

3 out of 5
West Kissimmee
CA $982

CA $842

per person
May 26 - May 31
Roundtrip non-stop flight included
Calgary (YYC) to Orlando (MCO)
4.4/5Excellent! (997 reviews)

"Private entrance. The private Hot tub. very roomy. Very safe, you never need to interact with other guests.…"

Reviewed on Mar. 5, 2021

Floridays Resort Orlando

Floridays Resort Orlando

3.5 out of 5
CA $889

CA $777

per person
May 23 - May 27
Roundtrip non-stop flight included
Calgary (YYC) to Orlando (MCO)
4.3/5Excellent! (9,828 reviews)

"Overall, very nice. The only complaint have is trying to find parking during the night hours. It can get very crowded and parking is very limited. Other than that, enjoyed my stay!…"

Reviewed on Apr. 14, 2021

Top Hotels in Winter Garden

The Grove Resort & Water Park Orlando
The Grove Resort & Water Park Orlando
4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Free cancellationReserve now, pay when you stay
The price is CA $243 per night from Apr 19 to Apr 20
4.4/5Wonderful! (5,468 reviews)

"The property caters to families with entertainment and the food was good."…"

Reviewed on Apr. 13, 2021

The Grove Resort & Water Park Orlando
Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel
Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel
4 out of 5
8505 W Irlo Bronson Memorial Hwy, Winter Garden, FL
Free cancellation
The price is CA $179 per night from Apr 19 to Apr 20
4.2/5Very Good! (1,605 reviews)

"I loved that you could drive right up to your condo! Thy also had 3 sections of resort with different pools at each location. Just because you were staying in North, you could still go see the West building etc! This was a great vacation and the staff, Miles is who checked us in, was fantastic!"…"

Reviewed on Apr. 13, 2021

Holiday Inn Club Vacations at Orange Lake Resort, an IHG Hotel
Liki Tiki Village by Diamond Resorts
Liki Tiki Village by Diamond Resorts
3.5 out of 5
17777 Bali Blvd, Winter Garden, FL
Free cancellationReserve now, pay when you stay
The price is CA $100 per night from May 11 to May 12
4.1/5Very Good! (3,229 reviews)

"The amenities were great, the staff was very helpful. The rooms werent as clean as expected."…"

Reviewed on Apr. 13, 2021

Liki Tiki Village by Diamond Resorts
See all 212 properties in Winter Garden
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.

Top things to do in Winter Garden

Image for Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

CA $178
Per adult
86% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Image for Kennedy Space Center Admission

Kennedy Space Center Admission

CA $77
Per adult
88% of travellers recommend
Kennedy Space Center Admission
Image for SEA LIFE Orlando Aquarium

SEA LIFE Orlando Aquarium

CA $40
Per adult
84% of travellers recommend
SEA LIFE Orlando Aquarium
See all activities in Winter Garden

Frequently asked questions

How much does a Winter Garden vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Winter Garden from just CA $648. And the more you bundle, the more money you save. Your dream vacation has never been so affordable.
If I'm not able to travel, can I cancel my Winter Garden vacation package?
Don’t stress if you’re rethinking your Winter Garden vacation package — you can cancel or amend your booking. And if you’ve booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We realize life can occasionally throw a spanner in the travel works, so head to our Customer Service Portal if that happens. When you’re ready to make changes, we’re ready to help.
How do I get a cheap travel package to Winter Garden?
Combine your flights and hotels, add extras such as activities or a rental car, and save up to C$590. A Winter Garden vacation package makes getting away on a budget easy. You won’t just pick up incredible discounts on your getaway — you’ll have loads of choice at your fingertips too. When you book through Expedia, you can select from more than 400 partner airlines and 321,000 properties worldwide. Your dream vacation begins right here, right now!
Where should I stay in Winter Garden?
With popular attractions like Orange Lake Golf and Orange County National Golf Club in this neighborhood, try to find a hotel situated near either of them. Resurrection Catholic Church is another Winter Garden sight that draws the crowds.
What are the top hotels in Winter Garden?
Book a room at The Grove Resort Orlando. It’s one of the area’s most sought-after hotels. Another well-known option in Winter Garden is Liki Tiki Village by Diamond Resorts.
When is the best time of year to visit Winter Garden?
There’s no right time or wrong time to visit Winter Garden. But if you’re eager to score big savings on your trip, consider the month of September. Airfares and hotel prices tend to spike in July. Winter Garden can get very busy in March, April, July, so if you want to escape the crowds, visit in December, November, October.
How far in advance should I book my Winter Garden vacation?
It depends on the air carrier, but it’s usually possible to look up international airfares on Expedia up to 12 months in advance. While it’s a good idea to book ahead of time, lucky travelers will sometimes score a cheaper flight just weeks before the date of departure.
What does an Expedia Winter Garden travel package include?
That depends on what you want. If you’re traveling by yourself, you might decide to combine flights and hotels. Bringing the whole crew to Winter Garden? A travel package that includes hotels, flights and rental cars might suit you better. Expedia gives you the freedom to customize your travel package.
What should I know before booking a Winter Garden travel package?
Whether it’s adventure or relaxation you’re chasing, a Winter Garden vacation package lets you organize your escape your way. Plus, you’ll score great discounts just for combining your hotel with your flights and rental car. The more you bundle, the more you’ll save!
Does Expedia offer Book Now, Pay Later Winter Garden vacation packages?
Expedia has teamed up with online lender Affirm to help ease any financial stress to do with your trip. This could be useful if your need to travel arose suddenly. Book Now, Pay Later and spread out the cost of your hotel and flight package booking over multiple installments.
Can I choose my airline with a Winter Garden Expedia vacation package?
Yes, of course. We offer more than 550 partner airlines globally, so opt for the carrier that fits your needs.

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