Winter Springs Vacation Packages

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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.

Top Winter Springs Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was CA $1,179, price is now CA $745 per person
CA $745
per person
Sep 21 - Sep 28
found 1 hour ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9/10 Wonderful! (3,664 reviews)
Ok

Reviewed on Jul 16, 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $2,110, price is now CA $984 per person
CA $984
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9/10 Wonderful! (1,275 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 complimentary BBQ facilities. I have been coming to Orlando for the past 10 years and will definitely return here. Location is fantastic too only $6 dollar taxi to Universal or you can pre-book their complimentary bus service. All in all loved our time here and highly recommend.

Reviewed on Jul 16, 2026

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was CA $3,391, price is now CA $1,895 per person
CA $1,895
per person
Aug 23 - Aug 30
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Orlando (MCO)
8.6/10 Excellent! (554 reviews)
The setup of the hotel is strange, there a different section of the hotel for you to stay, but if you are not familiar with the hotel, you might ask yourself, why you ended up in the from section of the hotel, facing the road, and not the pool area. If you decide to sleep late, this is not the hotel for you, since noises are coming from all over the place, my las 2 mornings, it was 8:30 and there was already workers all over the place being loud, and the noise from the room above it is expected to be there too. The pool is small, but the lazy river and the access to the beach are the positive sides.

Reviewed on Jul 9, 2026

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was CA $1,788, price is now CA $1,151 per person
CA $1,151
per person
Aug 31 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9.6/10 Exceptional! (1,150 reviews)
Quiet

Reviewed on Jul 16, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $2,637, price is now CA $1,732 per person
CA $1,732
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9.2/10 Wonderful! (1,003 reviews)

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Winter Springs Hotel Deals

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from Jul 20 to Jul 21
CA $251
CA $283 total
Jul 20 - Jul 21
includes taxes & fees
9.4/10 Exceptional! (4,315 reviews)
"The bed was the worst hard bed I have ever stayed. I tossed and turned all night long."

Reviewed on Jul 16, 2026

Hyatt Regency Orlando International Airport
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 CA $211 per night from Jul 21 to Jul 22
CA $211
CA $237 total
Jul 21 - Jul 22
includes taxes & fees
9/10 Wonderful! (7,206 reviews)
"our group is very like this resort this our secound time there ,staff very nice ,helpfull,pool is good ,and near volcano bay"

Reviewed on Jul 16, 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
The price is CA $146 per night from Aug 11 to Aug 12
CA $146
CA $164 total
Aug 11 - Aug 12
includes taxes & fees
9.2/10 Wonderful! (5,393 reviews)
"The room was spacious for my family of 5."

Reviewed on Jul 16, 2026

Universal's Endless Summer Resort - Dockside Inn and Suites
See all 4,892 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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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

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.
See properties

What to do in Winter Springs

Barn Day for Little Cowboys and Cowgirls

Barn Day for Little Cowboys and Cowgirls

CA $7
per adult
Barn Day for Little Cowboys and Cowgirls
The Underground Experience

The Underground – Orlando’s Ultimate Tactical Group Experience

CA $70
per adult
The Underground – Orlando’s Ultimate Tactical Group Experience
Simulated Shooting Range

Bill Drill: All-Ages Tactical Adventure in Orlando

CA $140
per adult
100% of travellers recommend
Bill Drill: All-Ages Tactical Adventure 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 CA $745 on Expedia for your Winter Springs getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Winter Springs costs.
What are the cheapest months to go to Winter Springs?
Travel in the low or shoulder season and you're likely to get cheap Winter Springs vacation packages. Bear in mind that school vacation periods and major festivals and events can have an impact on prices, so do a little research before you go.
How many days is enough for Winter Springs?
Typically, a handful of days is enough to check out the major sights during your Winter Springs vacation. However, if you prefer to have some time to relax or take day tours, consider extending your itinerary.
Is it worth booking a vacation package to Winter Springs?
Winter Springs has everything you need for an amazing escape. Begin your Winter Springs vacation on a high note by checking out popular attractions like Central Winds Park.
How to find the best Winter Springs package deals?
Use Expedia's filters to help you find some great Winter Springs package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Winter Springs package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Winter Springs vacation as a package?
You can enjoy significant savings on your next Winter Springs retreat by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Winter Springs?
If you have your Winter Springs travel dates finalized, book early to bag some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Winter Springs?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Winter Springs.
  2. Budget wisely: In addition to the cost of your hotel, you should consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Winter Springs.
  3. Decide how many days away: Start by compiling a list of the activities and sights you'd like to experience in Winter Springs. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Winter Springs vacation package that brings all your bookings together.

Explore a world of travel with Expedia

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