Winter Springs Vacations from ¥186,198

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The Latest Winter Springs Vacation Packages

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

Palazzo Lakeside Hotel

¥186,198
per person
Nov 16 - Nov 23
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
8.4/10 Very Good! (5,311 reviews)
Excellent property an Nice friendly Staff. I enjoy the environment staying here. Great for your money.

Reviewed on Aug 25, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

¥310,427
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.2/10 Wonderful! (1,006 reviews)
Everything was nice clean

Reviewed on Aug 22, 2026

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

¥240,578
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.2/10 Wonderful! (1,393 reviews)
Magic Village Yards, Trademark Collection by Wyndham

Magic Village Yards, Trademark Collection by Wyndham

¥323,218
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.2/10 Wonderful! (1,203 reviews)
The Delaney Hotel

The Delaney Hotel

South Orange
¥268,940
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.6/10 Exceptional! (1,187 reviews)

Find the Best Winter Springs Vacation Packages

Winter Springs Hotel Deals

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

5780 Major Blvd Orlando FL
¥11,272
¥12,680 total
Sep 7 - Sep 8
includes taxes & fees
DoubleTree by Hilton at the Entrance to Universal Orlando
Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
¥23,864
¥26,846 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (7,592 reviews)
"My family & I have been Vacationing there 5 years straight. We love it!"

Reviewed on Aug 26, 2026

Universal's Cabana Bay Beach Resort
Universal's Endless Summer Resort - Dockside Inn and Suites

Universal's Endless Summer Resort - Dockside Inn and Suites

7125 Universal Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
¥19,582
¥22,030 total
Aug 27 - Aug 28
includes taxes & fees
9.2/10 Wonderful! (5,659 reviews)
"Great value property"

Reviewed on Aug 26, 2026

Universal's Endless Summer Resort - Dockside Inn and Suites
See all 4,953 properties in Winter Springs
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 Springs attractions

A curved concrete path leading to a dock over a calm lake, surrounded by lush greenery and tall trees with Spanish moss.

Central Winds Park

Central Winds Park offers 103 acres of recreational paradise with award-winning sports fields and nature trails. Explore scenic paths along Lake Jesup or enjoy seasonal events in this community haven.
See properties
A covered pavilion with picnic tables and a large tree in the foreground.

Trotwood Park

Trotwood Park offers three diverse playgrounds and a refreshing splash pad amid serene natural ponds. Families can enjoy pavilions with barbecue grills or explore the scenic boardwalks for wildlife watching.
See properties

What to do in Winter Springs

St. Johns River High-Tea Cruise Tour in Sanford

St. Johns River High-Tea Cruise Tour in Sanford

¥7,802
per adult
St. Johns River High-Tea Cruise Tour in Sanford
Simulated Shooting Range

Bill Drill: All-Ages Tactical Adventure in Orlando

¥15,801
per adult
100% of travellers recommend
Bill Drill: All-Ages Tactical Adventure in Orlando
2-Hour Clear Kayak & Clear Paddleboar

2-Hour Clear Kayak and Paddleboard(SUP) Rental in Orlando

¥7,182
per adult
100% of travellers recommend
2-Hour Clear Kayak and Paddleboard(SUP) Rental in Orlando
See all activities in Winter Springs

Frequently asked questions

How much does a Winter Springs vacation package cost?
You'll find cheap prices from ¥186,198 on Expedia for your Winter Springs escape. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Winter Springs costs.
What are the cheapest months to go to Winter Springs?
Plan your getaway for the off-peak season and you're likely to get cheap Winter Springs vacation packages. Bear in mind that school vacation periods and major local events can impact prices, so do your research before booking.
How many days is enough for Winter Springs?
With a well-organized itinerary, you can easily hit the top Winter Springs sights in a handful of days. But if you prefer to venture off the beaten track or take day trips, consider booking your Winter Springs vacation for longer.
Is it worth booking a vacation package to Winter Springs?
Winter Springs is a good vacation destination with attractions like Central Winds Park among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Winter Springs vacation promises fun for everyone.
How to find the best Winter Springs package deals?
Use Expedia's filter tool to find some great Winter Springs package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Winter Springs package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Winter Springs vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally land a better deal than booking each component separately. And you'll still get the freedom to create a tailored Winter Springs vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Winter Springs?
Enjoy fantastic discounts by booking your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Winter Springs trip.
How to plan a trip to Winter Springs?
  1. Choose when to get away: Check your calendar and get packing. Your preferred season and the available activities will also help you decide when to vacation in Winter Springs.
  2. Set your budget: Consider expenses like transportation, flights and meals when calculating how much to save for your trip to Winter Springs. Then, select a hotel that works with your budget, whether that's a wallet-friendly stay or a lavish retreat.
  3. Decide how long to go for: Now that you know more about Winter Springs, you can figure out the perfect length of your break. Put together a draft plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your airfare and accommodations: Once you've settled on your trip dates and duration, book the perfect Winter Springs vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.