Winter Garden Vacations from AED4,052

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The Latest Winter Garden Vacation Packages

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

Seasons Florida Resort

2 out of 5
per person
Sep 16 - Sep 20
found 19 hours ago
Roundtrip flight included
Birmingham (BHX) to Orlando (MCO)
8.8/10 Excellent! (3,037 reviews)
Loved our stay here at Seasons Florida Resort! Excellent location in the Kissimmee area! The pool was very cool & fun. The room was big and clean and had everything we needed! Would definitely stay again!

Reviewed on 12 August 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Sep 16 - Sep 20
found 19 hours ago
Roundtrip flight included
Birmingham (BHX) to Orlando (MCO)
8.8/10 Excellent! (1,013 reviews)
It was a very comfortable place to stay. Well equipped for everything you need and it feels you’re home. The location is in the center from the theme parks, shopping and restaurants. Everything comes easy on this place and area. We stayed 6 nights and we slept well and good

Reviewed on 14 August 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Sep 16 - Sep 20
found 19 hours ago
Roundtrip flight included
Birmingham (BHX) to Orlando (MCO)
8.2/10 Very Good! (5,177 reviews)
Totally enjoyed our stay

Reviewed on 16 August 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
per person
Sep 16 - Sep 20
found 19 hours ago
Roundtrip flight included
Birmingham (BHX) to Orlando (MCO)
9.6/10 Exceptional! (1,000 reviews)
Excellent, loved the location and atmosphere, also the free parking was a nice bonus

Reviewed on 10 August 2025

Club Wyndham Bonnet Creek

Club Wyndham Bonnet Creek

3.5 out of 5
per person
Sep 16 - Sep 20
found 19 hours ago
Roundtrip flight included
Birmingham (BHX) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
Clean Convenient Large space perfect for groups Lots of pool and food options

Reviewed on 22 May 2025

Where to stay in Winter Garden

Find the best Winter Garden areas and neighborhoods for the activities you enjoy most. Learn more about Winter Garden
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Vista del Lago

While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby.

Find hotels in Vista del Lago

Find the Best Winter Garden Vacation Packages

Winter Garden Hotel Deals

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
Fully refundableReserve now, pay when you stay
The price is AED 403 per night from Aug 25 to Aug 26
AED 403
AED 453 total
25 Aug - 26 Aug
includes taxes & fees
9.2/10 Wonderful! (4,452 reviews)
"very good"

Reviewed on 15 August 2025

Home2 Suites by Hilton Orlando at Flamingo Crossings
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is AED 511 per night from Aug 17 to Aug 18
AED 511
AED 740 total
17 Aug - 18 Aug
includes taxes & fees
7.8/10 Good! (8,333 reviews)
"I liked the facilities and water park I didn’t like the lack f food options"

Reviewed on 13 August 2025

The Grove Resort & Water Park Orlando
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

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

2.5 out of 5
631 FLAGLER AVE, Winter Garden, FL
Fully refundableReserve now, pay when you stay
The price is AED 342 per night from Sep 1 to Sep 2
AED 342
AED 384 total
1 Sep - 2 Sep
includes taxes & fees
9.4/10 Exceptional! (3,656 reviews)
"Amazing"

Reviewed on 15 August 2025

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
See all 53,766 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.

Discover the most popular places to visit in Winter Garden

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 walkable area.

Flamingo Crossings Town Center

Orange County National Golf Club

Enjoy a round of golf in Winter Garden at Orange County National Golf Club. Amble around this family-friendly area's lakeside or experience its entertainment choices.

Orange County National Golf Club

Disney's Palm Golf Course

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.

Disney's Palm Golf Course

Frequently asked questions

How much does a Winter Garden vacation package cost?
Offering great value package deals from AED4,052 on Expedia, you'll be thrilled with how little a vacation to Winter Garden costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Winter Garden?
If you're hoping to snag a cheap Winter Garden vacation package, consider visiting in February, September and October. You'll typically find lower prices on hotels and flights during these quieter months — perfect for a budget-friendly break.
How to find the best Winter Garden package deals?
Landing a cheap Winter Garden package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, apply some filters and browse what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most affordable Winter Garden package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winter Garden vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking accommodations and flights separately. Better still, you can tailor your Winter Garden escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Winter Garden?
If you've got your Winter Garden vacation dates locked in, book as soon as you can to bag some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Winter Garden?

  1. Choose when to get away: Check your diary and get your bags packed. Your favorite season and the type of activities on offer will also help you decide when to vacation in Winter Garden.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and dining out to activities and airfares. Your accommodations will likely be the largest expense during your trip to Winter Garden.
  3. Decide your trip length: Think about how much time you want to spend exploring Winter Garden. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Winter Garden vacation package that brings all your bookings together.