Deals on vacations and trips to Winter Park

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Winter Park flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $615, price is now $300 per person
$300
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $765, price is now $370 per person
$370
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel doesn't skimp on freebies - guests receive free WiFi, free self parking, and a free theme park shuttle. Business travelers can take advantage of the express check-out. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
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 $1,014, price is now $523 per person
$523
per person
Jan 29 - Feb 5
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This hotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.
Ocean Landings Resort and Racquet

Ocean Landings Resort and Racquet

2.5 out of 5
Save 100% on your flight
Price was $1,287, price is now $704 per person
$704
per person
Jan 13 - Jan 20
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free hotel features 2 outdoor pools, a hot tub, and a restaurant. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. A coffee shop, laundry facilities, and barbecue grills are also on offer.
Oceanique Resort

Oceanique Resort

3.5 out of 5
Save 100% on your flight
Price was $1,639, price is now $914 per person
$914
per person
Jan 13 - Jan 20
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.

Top Winter Park hotels deals

Hyatt Regency Orlando International Airport

Hyatt Regency Orlando International Airport

4 out of 5
9300 Jeff Fuqua Boulevard Orlando FL
Free Cancellation
Reserve now, pay when you stay
$215 nightly
The price is $242 total per night
$242 total
Nov 23 - Nov 24
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.
Pool
Free WiFi
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $125 total per night
$125 total
Dec 13 - Dec 14
Total with taxes and fees
This smoke-free aparthotel features 3 restaurants, 6 outdoor pools, and 10 outdoor tennis courts. There's fun for all ages with a free kid's club and mini golf, and barbecue grills are available on site. Enjoy the 8 hot tubs and perks like free WiFi.
Pool
Hot Tub
Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista Orlando FL
Free Cancellation
Reserve now, pay when you stay
$96 nightly
The price is $108 total per night
$108 total
Dec 10 - Dec 11
Total with taxes and fees
This smoke-free aparthotel features a golf course, a full-service spa, and 3 restaurants. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the 4 outdoor pools and perks like free WiFi.
Pool
Hot Tub
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
Free Cancellation
$93 nightly
The price is $104 total per night
$104 total
Nov 29 - Nov 30
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a 24-hour gym. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Relax with a drink at one of the 2 bars/lounges and get perks like free WiFi.
Pool
Hot Tub
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
9500 Turkey Lake Rd Orlando FL
$116 nightly
The price is $131 total per night
$131 total
Nov 15 - Nov 16
Total with taxes and fees
This smoke-free hotel features a full-service spa, a water park, and a marina. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the 7 outdoor pools and get free valet parking.
Pool
Hot Tub
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

4 out of 5
12401 International Dr Orlando FL
Free Cancellation
Reserve now, pay when you stay
$96 nightly
The price is $108 total per night
$108 total
Dec 13 - Dec 14
Total with taxes and fees
This smoke-free aparthotel features 2 restaurants, 5 outdoor pools, and 2 outdoor tennis courts. Bring the family and enjoy the children's club, children's pool, and playground. Enjoy the 4 hot tubs and perks like free WiFi.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Winter Park
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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

A bar with wooden decor, a TV screen, and a bartender wearing a red jersey.
Photo by Jay Mullenix
Open 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.
See properties

Frequently asked questions

How much are vacation packages to Winter Park?
You can pick up a great flight and hotel bundle for a mere $300. With one of our Travelocity vacation packages, a getaway in Winter Park has never looked so good! Save some time and money and then get a start on packing those bags.
How long should my Winter Park vacation be?
Most travelers choose to spend about 2 nights in Winter Park, but how long you stay is your call. If you'd like to discover all the incredible things this destination has waiting for you, why not hang around a while longer?
Where can I get the best vacation package deals for Winter Park?
There are fantastic Winter Park package deals to snap up with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties around the globe? Keep that in mind when you're ready to cross another place off your bucket list.
Why should I purchase my Winter Park vacation package via Travelocity?
With first-rate service, 24/7 customer support and some of the most gorgeous getaways money can buy, you'll never roam alone. And if you find a cheaper price, we'll match it. That's our Price Match Guarantee.
Will I save money on my Winter Park car rental if I book it with a hotel or flight?
With a Winter Park vacation package, you can bundle your car, flight and hotel bookings and save a tidy sum. When you're ready to uncover the best of this wonderful region, why not make tracks to Daytona International Speedway? This top sight is 45 mi from Winter Park. With your own rental car, you'll be there soon enough.
Which airport is best for Winter Park?
Many travelers fly into Orlando Intl. Airport (MCO), 12 mi south of downtown Winter Park. Others prefer Daytona Beach Intl. Airport (DAB) (45 mi away from central Winter Park) or Orlando Sanford Intl. Airport (SFB) (13 mi away from central Winter Park).
What is there to do in Winter Park?
While venturing off the beaten track is rewarding, you really shouldn't miss the big sights that make a place famous. Full Sail University and Rollins College are a couple of them in Winter Park.
Where should I stay when visiting Winter Park?
The Hilton Garden Inn Winter Park is popular with many travelers. Book as soon as possible before it's too late.

Photos of local treasures

Browse Winter Park vacation photos for more inspiration

A clock with 'Winter Park' and 'Central Park' inscribed, surrounded by lush greenery and trees.
A brick building with a sign reading "Winter Park Historical Museum" and a large poster depicting a historical scene.
A neoclassical pavilion with columns and a curved roof, surrounded by lush greenery and trees.
An aerial view of a park with a circular central area, pathways, and a body of water with lily pads.
A nighttime cityscape with a reflection of fireworks in a body of water.

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