A clear lake surrounded by trees and a concrete walkway.

Winter Springs Vacations from $260

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The Latest Winter Springs Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Oct 6 - Oct 11

    Westgate Vacation Villas Resort + Flight

    Kissimmee
    5 nights
    4.0 star property
    8.2/10 - Very Good (2,022 reviews)
    Roundtrip New York (EWR) - Orlando (MCO)
    EWR - MCONonstop MCO - EWRNonstop
    Save 100% on your flight
    $591
    $260
    per traveler
    found 1 day ago
    Westgate Vacation Villas Resort
  • Oct 6 - Oct 11

    Palazzo Lakeside Hotel + Flight

    Kissimmee
    5 nights
    3.0 star property
    8.4/10 - Very Good (5,209 reviews)
    "It was giving rushed/low budget project. In the sense that they could've invested in minor small room details. The hotel was divided into 3 buildings, yet only 1 ice machine for all. It was always out of ice! Single occupant with no kids, I definitely didn't appreciate the loud comings of children and parents at midnight. I couldn't tell which was louder. Housekeeping was every 3 days BUT make sure to request on 2nd day or you'll get skipped. No garbage can other then the bathroom garbage. I bet..."
    Reviewed July 16, 2026
    Roundtrip New York (EWR) - Orlando (MCO)
    EWR - MCONonstop MCO - EWRNonstop
    $1,124
    $267
    per traveler
    found 1 day ago
    Palazzo Lakeside Hotel
  • Aug 31 - Sep 5

    Westgate Palace Hotel / Universal / I-Drive + Flight

    International Drive District
    5 nights
    4.0 star property
    9.0/10 - Wonderful (1,290 reviews)
    "Marlyn on reception was so helpful during our check-in - thank you. We had a 2 bedroom apartment on the 14th floor which had fantastic views towards Epic and SeaWorld. The apartment was fully fitted with everything you need. Washing machine and dryer, full cooking facilities including a dishwasher. The furniture was all modern and had TVs in every room. In the communal areas the gym was great, the pool area was well maintained and relaxed (no lifeguard). Saw other guests using the..."
    Reviewed July 16, 2026
    Roundtrip New York (EWR) - Orlando (MCO)
    EWR - MCONonstop MCO - EWRNonstop
    $1,044
    $429
    per traveler
    found 1 day ago
    Westgate Palace Hotel / Universal / I-Drive
  • Oct 6 - Oct 11

    Westgate Towers Resort + Flight

    Kissimmee
    5 nights
    3.5 star property
    8.6/10 - Excellent (1,001 reviews)
    "This was our 2nd time staying here. Rooms are amazing. Highly recommended."
    Reviewed July 5, 2026
    Roundtrip New York (EWR) - Orlando (MCO)
    EWR - MCONonstop MCO - EWRNonstop
    Save 100% on your flight
    $584
    $260
    per traveler
    found 1 day ago
    Westgate Towers Resort
  • Sep 20 - Sep 26

    Seasons Florida Resort + Flight

    Kissimmee
    6 nights
    2.0 star property
    9.0/10 - Wonderful (3,713 reviews)
    "Ok"
    Reviewed July 16, 2026
    Roundtrip New York (EWR) - Orlando (MCO)
    EWR - MCONonstop MCO - EWRNonstop
    Save 100% on your flight
    $563
    $291
    per traveler
    found 1 day ago
    Seasons Florida Resort

What to do in Winter Springs

Winter Springs Hotel Deals

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.

Frequently Asked Questions

How much does a Winter Springs vacation package cost?

You'll find cheap prices from $260 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.