Winter Springs Vacations from $501

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Your Winter Springs Vacation

Say bye-bye to the worries of planning and hello to a Winter Springs vacation package. With everything organized before you leave, you can focus on discovering the best of this city, starting with Ivanhoe Village, which is great for dining, bars and pubs and shopping. If taking in sights is on the cards during your trip to Winter Springs, swing by leading attractions like Altamonte Mall, Winter Park Village and Cranes Roost Park. Your Winter Springs vacation is a couple of clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored just for you.

The Latest Winter Springs vacation packages

Price found within the past 48 hours. Click for updated prices.
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 $1,040, price is now $501 per person
$501
per person
Nov 12 - Nov 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,346 reviews)
Free shuttles and close proximity to universal and sea world. Family friendly and a-lot of activities for the entire family. Fire pits, mini golf, bikes, pizza and ice cream all without leaving the property. Adults can enjoy yoga, Starbucks, the pool bar and drafts bar & grill. I would stay again in Orlando.

Reviewed on Oct 12, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $3,125, price is now $1,517 per person
$1,517
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (486 reviews)
Excellent property to go too. Lazy river was night and the staff at the front desk was amazing. Very close to the beach with many restaurants and shops to walk too. Even saw Space X launch a rocket from this location. Perfect spot for a great price. Recommend especially if you're bring Children.

Reviewed on Oct 10, 2025

Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Save 100% on your flight
Price was $1,013, price is now $504 per person
$504
per person
Dec 17 - Dec 23
found 17 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.4/10 Exceptional! (1,002 reviews)
Very clean well maintained quiet property in a great location. Very nice pool and hot tub on the lake. They have fishing tackle that we used. Also kayaks, paddle boats and pool toys. Was nice and quiet compared to the large larger resorts that charge for these activities but also have a ton of people. Highly recommend this place.

Reviewed on Oct 1, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $1,475, price is now $738 per person
$738
per person
Dec 22 - Dec 29
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,360 reviews)
Over All It Was Great Me And My Kids Had Wonderful Time And Wanna Go Back

Reviewed on Oct 1, 2025

Summerville Vacation Homes by Columbia Management

Summerville Vacation Homes by Columbia Management

4 out of 5
Price was $2,379, price is now $1,206 per person
$1,206
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.4/10 Very Good! (151 reviews)
Exactly what we needed for our stay in Disney. Was first time we have stayed off property and besides not getting in to the park early, this place was great. It rained on us every day at the park and was nice to be able to through our jacket in the dryer! On negative i will say is the washer and dryer was loud HA! But other than that place had everythign we needed. Oh and fyi this place was not 3 bed rooms. It was 4! Maybe because it didtn have a bathroom? Not sure but was 4 bedroom 3 and half bath. HA kids liked havign there own rooms with own bathrooms. And so did I! Was thankful we was not crammed on an on park hotel with one room and one bathroom! Had 2 masters with Kings, one upstairs one down, and then the other 2 rooms was up stairs with one being two twins with bathroom then the other room was just a bunk. Would stay here again for sure.

Reviewed on Oct 9, 2025

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Discover the most popular places to visit in Winter Springs

Tuscawilla Golf Course

Enjoy a round of golf in Winter Springs at Tuscawilla Golf Course. Stroll along the lakeside or attend a sporting event in the area.

Tuscawilla Golf Course

Central Winds Park

After visiting Central Winds Park, make a plan to see the other sights and activities in Winter Springs. Amble around the area's lakeside or attend a sporting event.

Central Winds Park

Trotwood Park

After visiting Trotwood Park, make a plan to see the other sights and activities in Winter Springs. Experience the area's entertainment choices or attend a sporting event.

Trotwood Park

What to do in Winter Springs

Orlando: Central Florida Zoo Skip-the-Line Ticket

Orlando: Central Florida Zoo Skip-the-Line Ticket

$22
per adult
Orlando: Central Florida Zoo Skip-the-Line Ticket
Orlando: Unlimited Florida Internet with eSIM Mobile Data Plan

Orlando: Unlimited Florida Internet with eSIM Mobile Data Plan

$3
per traveler
Orlando: Unlimited Florida Internet with eSIM Mobile Data Plan
Wekiva River Guided Kayak Tour

Wekiva River Guided Kayak Tour

$100
per adult
Wekiva River Guided Kayak Tour
See all activities in Winter Springs

Winter Springs Hotel Deals

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

3.5 out of 5
6550 Adventure Way, Orlando, FL
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $150 total per night from Nov 5 to Nov 6
$150 total
Nov 5 - Nov 6
Total with taxes and fees
8.8/10 Excellent! (5,387 reviews)
"We enjoyed our stay!"

Reviewed on Oct 12, 2025

Universal's Cabana Bay Beach Resort
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $94 total per night from Nov 5 to Nov 6
$94 total
Nov 5 - Nov 6
Total with taxes and fees
8.4/10 Very Good! (5,055 reviews)
"Great"

Reviewed on Oct 11, 2025

Rosen Inn at Pointe Orlando
DoubleTree by Hilton Orlando Airport

DoubleTree by Hilton Orlando Airport

4 out of 5
5555 Hazeltine National Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $105 total per night from Oct 26 to Oct 27
$105 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (1,892 reviews)
"Airport shuttle pick up was quick and easy. Appreciated the friendly staff after a long travel day. The room was OK for the value - bed was squeaky. I would stay here again."

Reviewed on Oct 12, 2025

DoubleTree by Hilton Orlando Airport
See all 4,570 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.

Winter Springs Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Orlando Intl. Airport (MCO)
Population
34,800
Max Temp Winter
70ºF
Max Temp Summer
90ºF
Top Sights
Central Florida Zoo & Botanical Gardens, Sanford Museum and Wayne Dench Performing Arts Center

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Frequently asked questions

How much does a Winter Springs vacation package cost?
You'll find cheap prices from $501 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?
You can typically find lower prices and greater availability in July, August and December. Check out our cheap Winter Springs vacation packages and you could land some great off-season deals.
How many days is enough for Winter Springs?
Usually, a handful of days is enough to check out the top sights during your Winter Springs vacation. But if you'd like to have some time to unwind or take day tours, think about extending your itinerary.
Is it worth booking a vacation package to Winter Springs?
It's easy to see why a Winter Springs vacation is on the to-do list of many travelers. Leading attractions like Central Winds Park are just the beginning of things to keep you busy here.
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. Pick your travel dates: The things you plan to do in Winter Springs and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: On top of the cost of your hotel, you'll need to consider other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that may arise during your trip to Winter Springs.
  3. Organize your Winter Springs escape with Expedia's trip planning tool: Look for and book hotels and activities all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Winter Springs together.
  4. Decide how many days away: Start by listing all the activities and attractions you'd like to experience in Winter Springs. Then, estimate how long you'll need at each, including any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Winter Springs vacation package.
  6. Book any activities or day trips: Now to the fun part — organizing everything you want to do and see. Explore some of the best things to do in Winter Springs in Winter Springs and book your tickets in advance to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Winter Springs vacation packages?
Your Winter Springs getaway should be an escape from your daily routine, not a reason for money-related stress. So to allow you that extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.