Winter Park Vacation Packages
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Your Winter Park Vacation
When a getaway to the city is calling, answer it with a Winter Park vacation package. The neighborhood of Ivanhoe Village, which is great for dining, bars and pubs and shopping, makes a fantastic base for your adventures. Rollins College, Full Sail University and Altamonte Mall are just a few of the attractions worth exploring during your trip to Winter Park. Stop daydreaming and start adventuring. Check out the many options on Expedia today and put your Winter Park vacation plans in motion!
Top Winter Park Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
CA $1,510
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)
The unit itself is beautiful. The bedrooms and bathrooms are gorgeous with really nice furnishings. The showers are really nice and each bedroom has an attached bathroom, which is very convenient.
There were a few issues with cleanliness in the unit and the pool. We had stained washcloths in one bathroom, the sofa fabric is pilling and we found several items on the kitchen floor that hadn't been swept up. The pool filter doesn't appear to work well at all. We continually skimmed the pool but there was still dirt and leaves in the bottom of the pool that never went away.
The pictures in the listing show the pool as having an attached hot tub. It does not. It also shows loungers by the pool, but there are none. I did call the front desk to advise them of this. I asked for loungers to be delivered but they will not do that as it seems it's the responsibility of the owners to provide those. They didn't have much to say about the pool not having the hot tub, even though it is advertised as having one so that was disappointing.
The resort lobby is beautiful and check in was fairly easy. The resort pools and hot tubs were very nice as well. The pool bar food and drinks are expensive ($40 for a drink and hummus appetizer) and an automatic 20% gratuity is automatically added to all orders. Something to keep in mind.
Overall, we had a great stay and would definitely do it again, although I would not rent this particular unit the next time.
Reviewed on Sep 14, 2026
Ready to book your vacation to Winter Park?
Winter Park Hotel Deals
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
CA $292
CA $329 total
Sep 21 - Sep 22
includes taxes & fees
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
CA $190
CA $214 total
Oct 18 - Oct 19
includes taxes & fees
9.2/10 Wonderful! (6,759 reviews)
"We had a one bedroom with kitchen, the room also had a jacuzzi. Our flight was delayed so didn’t get to utilise the apartment but were very happy the few hours we spent there and would recommend"
Reviewed on Sep 17, 2026
Marriott's Grande Vista
5925 Avenida Vista Orlando FL
Fully refundableReserve now, pay when you stay
CA $134
CA $150 total
Oct 12 - Oct 13
includes taxes & fees
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.
Stay near popular Winter Park attractions
Photo by Jay Mullenix
Full Sail University
8.4/10 (73 reviews)
Enjoy the collegiate vibe when you visit Full Sail University, during your trip to Winter Park. Discover the area's top-notch restaurants and its acclaimed theater scene.
Casa Feliz Historic Home Museum
9.2/10 (34 reviews)
This house serves as the backbone for preserving other historic buildings in the city. Visit this beautiful building for its cultural events.
Kraft Azalea Gardens
9.6/10 (24 reviews)
Love is in the air practically everywhere you go in this park. Spend serene time under the trees near a lake where birds offer entertainment.
Lake Virginia
9.8/10 (32 reviews)
Cruise the waterway to see expansive homes and wildlife in this former citrus-growing town. A chain of lakes lets you see the city from a unique perspective.
Morse Museum of American Art
9.8/10 (68 reviews)
If you admire Tiffany lamps and chandeliers, visit this museum to see the most comprehensive collection of works by the designer behind them.
Photo by Matt Merkel
Winter Park Country Club
9.4/10 (3 reviews)
Enjoy a round of golf in Winter Park at Winter Park Country Club. Wander around the area's picturesque gardens or experience its great live music.
Winter Park Village
9.6/10 (323 reviews)
During your trip to Winter Park, you can enjoy retail therapy at Winter Park Village. Stroll along the area's lakeside, or simply savor its top-notch restaurants.
Lee Road Shopping Center
9.0/10 (38 reviews)
During your visit to Winter Park, you can search for that perfect souvenir at Lee Road Shopping Center. Wander the lakeside and picturesque gardens in the area.
What to do in Winter Park
Universal Orlando Resort Theme Park Tickets (US & Canada)
CA $194
per adult
86% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
CA $38
per adult
92% of travellers recommend
Walt Disney World® Resort Mickey’s Not-So-Scary Halloween Party
CA $220
per adult
100% of travellers recommend
Frequently asked questions
How much does a Winter Park vacation package cost?
You can pick up a vacation package to this destination from CA $588 on Expedia. But how much your vacation to Winter Park costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Winter Park?
January, February and July are great times to look for cheap Winter Park vacation packages. Opting to travel in quieter periods means you can usually find lower prices on accommodations and flights.
How many days is enough for Winter Park?
Allow at least 2 days for your Winter Park vacation if you're hoping to immerse yourself in everything that makes this destination special. Stroll around popular areas, including Northeast Orlando and Ivanhoe Village. Then check out top attractions such as Tinker Field and Dr. Phillips Centre for the Performing Arts. With a well-planned itinerary, you'll be kept busy with room for some relaxation too. Want to go beyond Winter Park? Consider an excursion or two.
Is it worth booking a vacation package to Winter Park?
Winter Park has all the ingredients you need for a fantastic getaway — golfing, shopping and markets are just the start. Whether you want to visit sights like Casa Feliz Historic Home Museum and Albin Polasek Museum and Sculpture Gardens, or take the path less travelled, you'll find plenty to experience on your Winter Park vacation.
How to find the best Winter Park package deals?
Bagging a cheap Winter Park package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Winter Park package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Winter Park vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Winter Park vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Winter Park?
If you're planning a spontaneous Winter Park trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Winter Park?
- Choose when to get away: Check your schedule and get your bags packed. Your favourite season and the activities available will also help you decide when to escape to Winter Park.
- Set your budget: Consider expenses like flights, food and transportation when calculating how much to save for your trip to Winter Park. Then, select a property that suits your budget, whether that's a wallet-friendly option or a more upscale getaway.
- Decide how many days away: Start by making a list of all the sights and activities you'd like to get to in Winter Park. Then, estimate how long you'll need at each, including any travel time.
- Combine your accommodations and airfare: After you've settled on your dates and duration, lock in the ideal Winter Park vacation package for you.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
