Winter Springs Vacations from $432

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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 Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Save 100% on your flight
Price was $837, price is now $432 per person
$432
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,253 reviews)
It was a very nice clean property just a bit smaller unit size than what we’re used to!

Reviewed on May 25, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $930, price is now $451 per person
$451
per person
Aug 4 - Aug 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (1,734 reviews)
Es super increíble me encantó

Reviewed on May 31, 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $929, price is now $467 per person
$467
per person
Aug 1 - Aug 8
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (1,936 reviews)
This was a amazing resort with so many amenities and the Mexican restaurant was great and the ice cream was yummy - rooms are clean and it is very family friendly

Reviewed on May 27, 2026

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $2,200, price is now $1,122 per person
$1,122
per person
Aug 18 - Aug 24
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (548 reviews)
Esta bien Accesible a todas las amenidades, incluyendo el área de la playa,Solo que es un poco caro el precio por noche, por lo demás todo muy bien.

Reviewed on May 25, 2026

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 $789, price is now $463 per person
$463
per person
Aug 15 - Aug 20
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
7.8/10 Good! (500 reviews)
The hotel was beautiful and staff were courteous. I’d booked this hotel because I wanted to enjoy the rooftop terrace, but upon arrival was told that I couldn’t because I wasn’t a club member. I was put on the highest floor and within two days both elevators were out of service so all guests had to use the service elevator in that part of the building. I had also booked for the breakfast, but it was over by 9:30 so I never made it. Also, on separate occasions, the power went out in my room thus rotting the food that I had in the refrigerator. Finally, the TVs were not set up appropriately, I only had a few live channels, and the guide had no information and no premium channels.

Reviewed on May 10, 2026

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Discover the most popular places to visit in Winter Springs

Central Winds Park on Lake Jesup in Winter Springs, a suburb of Orlando, Florida

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 Gazebo Winter Springs, Florida

Trotwood Park

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

Trotwood Park

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

What to do in Winter Springs

Wekiva River Guided Kayak Tour

Wekiva River Guided Kayak Tour

$100
per adult
Wekiva River Guided Kayak Tour
Solve Puzzles and Escape Woods Experience in Orlando

Solve Puzzles and Escape The Woods Experience in Orlando

$32
per adult
Solve Puzzles and Escape The Woods Experience in Orlando
2-Hour Clear Kayak & Clear Paddleboar

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

$45
per adult
100% of travellers recommend
2-Hour Clear Kayak and Paddleboard(SUP) Rental in Orlando
See all activities in Winter Springs

Winter Springs Hotel Deals

DoubleTree by Hilton at the Entrance to Universal Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4 out of 5
5780 Major Blvd Orlando FL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $101 total per night from Jun 14 to Jun 15
$101 total
Jun 14 - Jun 15
Total with taxes and fees
8.6/10 Excellent! (6,938 reviews)
"Been better but maintained as well as it could with as many guest but parking price is ridiculous property needs to b be upgraded"

Reviewed on May 31, 2026

DoubleTree by Hilton at the Entrance to Universal Orlando
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
$147 nightly
The price is $166 total per night from Jun 15 to Jun 16
$166 total
Jun 15 - Jun 16
Total with taxes and fees
9/10 Wonderful! (6,882 reviews)
"Very clean and updated room! Everything smelled and looked fresh and kept very nice. Loved the amenities and never had any issues with noise or smell!"

Reviewed on May 31, 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

3 out of 5
7125 Universal Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $163 total per night from Jun 22 to Jun 23
$163 total
Jun 22 - Jun 23
Total with taxes and fees
9.2/10 Wonderful! (5,341 reviews)
"Great"

Reviewed on Jun 1, 2026

Universal's Endless Summer Resort - Dockside Inn and Suites
See all 4,800 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.

Find the Best Winter Springs Vacation Packages

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 $432 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.