Winter Springs Holidays

Photo by Stephanie Moraca

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Top Flight + Hotel Deals in Winter Springs

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

Palazzo Lakeside Hotel

3 out of 5
Price was €512, price is now €206 per person
€206
per person
26 Sept - 28 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,171 reviews)
Gould be a good idea to provided some info how to open the gate

Reviewed on 24 Aug 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was €424, price is now €303 per person
€303
per person
26 Sept - 28 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.6/10 Exceptional! (1,000 reviews)
Very spacious hotel, great staff and nice location

Reviewed on 23 Aug 2025

Conrad Orlando at Evermore

Conrad Orlando at Evermore

5 out of 5
Price was €1,587, price is now €1,222 per person
€1,222
per person
27 Oct - 30 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
9.4/10 Exceptional! (268 reviews)
Amazing luxurious property! The Evermore lagoon and private beach area for Conrad guests was incredible! Staff were extremely friendly and helpful! Will definitely visit again!

Reviewed on 21 Aug 2025

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

Waldorf Astoria Orlando - An Official Walt Disney World® Hotel

5 out of 5
Price was €574, price is now €447 per person
€447
per person
26 Sept - 28 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.2/10 Wonderful! (329 reviews)
Good location for visiting the parks.

Reviewed on 17 Aug 2025

Villatel Orlando Resort

Villatel Orlando Resort

4 out of 5
International Drive District
Price was €749, price is now €597 per person
€597
per person
26 Sept - 28 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.2/10 Wonderful! (191 reviews)
Had the best time visiting this resort in mid Aug! Rented the 4BR w/pool & game room! Family of 6 fit extremely well in the home! Home was super clean, well stocked, plenty of all toiletries, dry goods & linens. Kids LOVED the game room!!! The beds, OMG, so SO comfortable!! Like better than our $10k bed at home! Pools were super fun, so fun that we extended a day! Evening swims were awesome, music choice by management-well done!! Pool food was priced well for a resort, not overpriced at all IMO. And the food was actually good!! The burger- so good. Complex is super safe, we felt comfortable letting our kids (15yrs-6yrs) play on their own around the pool area while hubs and I laid out. We had the best time & already planning a trip back! Ty so much

Reviewed on 23 Aug 2025

Top hotels in Winter Springs

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
The price is €89 per night from 10 Sept to 11 Sept
€89
10 Sept - 11 Sept
includes taxes & fees
8.2/10 Very Good! (6,543 reviews)
"Very convenient for Universal across the street. Extra parking fees unexpected, but convenient."

Reviewed on 21 Aug 2025

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
The price is €132 per night from 24 Sept to 25 Sept
€132
24 Sept - 25 Sept
includes taxes & fees
8.8/10 Excellent! (5,124 reviews)
Cabana Bay
"The resort was very nice , clean and well maintained. Bus service to parks was a great convenience. Stayed in building 7 , it was annoying to come bat to bldg every night and have smokers at the entrance, and sometimes smoking pot. With kids , that should not have to be exposed to that."

Reviewed on 21 Aug 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
The price is €98 per night from 30 Aug to 31 Aug
€98
30 Aug - 31 Aug
includes taxes & fees
8.4/10 Very Good! (4,814 reviews)
Awesome overnight!
"Great room and service! Perfect location with lots of walkable attractions!"

Reviewed on 23 Aug 2025

Rosen Inn at Pointe Orlando
See all 4,474 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.

What to do in Winter Springs

Orlando: Central Florida Zoo Skip-the-Line Ticket

Orlando: Central Florida Zoo Skip-the-Line Ticket

€19
per adult
80% of travellers recommend
Orlando: Central Florida Zoo Skip-the-Line Ticket
2-Hour Clear Kayak & Clear Paddleboar

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

€39
per adult
100% of travellers recommend
2-Hour Clear Kayak & Clear Paddleboard(SUP) Rental in Orlando
Sailing Tour - Orlando, FL - Sailing Orlando

Private 2-Hour Day Sailing Experience

€72
per adult
Private 2-Hour Day Sailing Experience
See all activities in Winter Springs

Frequently asked questions

How much does a Winter Springs holiday package cost?
You'll find cheap prices from €206 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 holiday 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 holiday packages. Bear in mind that school holiday 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-organised 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 holiday for longer.
Is it worth booking a holiday package to Winter Springs?
Winter Springs is a good holiday 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 holiday 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 holiday package as early as possible.
Is it cheaper to book a Winter Springs holiday as a package?
Expedia holiday 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 holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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 holiday 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 accommodation: Once you've settled on your trip dates and duration, book the perfect Winter Springs holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.