Deals on vacations and trips to Winter Park, FL

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Winter Park flight + hotel vacation packages

Westgate Leisure Resort

Westgate Leisure Resort

3.5 out of 5
Price was $738, price is now $375 per person
per person
Mar 8 - Mar 12
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
2 outdoor pools, a spa tub, and a gym are all featured at this smoke-free resort. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, a garden, and a grocery/convenience store are also on offer.
Seralago Hotel & Suites Main Gate East

Seralago Hotel & Suites Main Gate East

3 out of 5
Save 100% on your flightPrice was $346, price is now $183 per person
per person
Mar 15 - Mar 22
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free hotel features 2 outdoor pools, an outdoor tennis court, and a restaurant. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the 24-hour gym and perks like free self parking and a free shopping center shuttle.
Westgate Palace a Two Bedroom Condo Resort

Westgate Palace a Two Bedroom Condo Resort

4 out of 5
Florida Center
Price was $1,264, price is now $682 per person
per person
Mar 5 - Mar 12
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This resort features an outdoor pool, a gym, and a restaurant. Bring the family and enjoy the children's pool, playground, and kid-friendly dining. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.
Embassy Suites by Hilton Orlando Lake Buena Vista South

Embassy Suites by Hilton Orlando Lake Buena Vista South

3.5 out of 5
Save 100% on your flightPrice was $599, price is now $401 per person
per person
Feb 28 - Mar 4
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
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. Enjoy the spa tub and free full breakfast each morning.
CLC Encantada Resort Vacation Townhomes

CLC Encantada Resort Vacation Townhomes

3 out of 5
Save 100% on your flightPrice was $723, price is now $485 per person
per person
Mar 9 - Mar 14
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free aparthotel features 2 outdoor pools, a 24-hour gym, and a restaurant. There's fun for all ages with a children's pool and a playground, and families will appreciate the picnic area. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.

Top Winter Park hotels deals

The Alfond Inn

The Alfond Inn

4 out of 5
300 East New England Avenue, Winter Park, FL
Free Cancellation
Reserve now, pay when you stay
The price is $254 per night
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 10 conference rooms, business center, and valet parking. Enjoy the gym and perks like free WiFi.
SpringHill Suites by Marriott Winter Park

SpringHill Suites by Marriott Winter Park

2.5 out of 5
1127 NORTH ORLANDO AVENUE, Winter Park, FL
Free Cancellation
Reserve now, pay when you stay
The price is $229 per night
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free airport shuttle. Enjoy the free full breakfast each morning.
Hilton Garden Inn Winter Park

Hilton Garden Inn Winter Park

3 out of 5
1275 Lee Road, Winter Park, FL
Free Cancellation
Reserve now, pay when you stay
The price is $179 per night
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 2 conference rooms, as well as the 24-hour business center and free WiFi in public areas. Free self parking and a safe deposit box are also offered on site.
Park Plaza Hotel

Park Plaza Hotel

3 out of 5
307 South Park Avenue , Winter Park, FL
Free Cancellation
Reserve now, pay when you stay
The price is $197 per night
An attached winery and a restaurant are featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Relax with a drink at the bar/lounge and enjoy the free continental breakfast each morning.
Winter Park Oasis

Winter Park Oasis

Winter Park, FL
The price is $134 per night
A garden is available at this vacation home.
Cute Winter Park Master Suite!!!

Cute Winter Park Master Suite!!!

Winter Park, FL
Get rates
Located in Goldenrod, this vacation home is 2 mi (3.3 km) from Full Sail University and within 6 mi (10 km) of Rollins College and Winter Park Village. Kraft Azalea Gardens and Albin Polasek Museum and Sculpture Gardens are also within 6 mi (10 km).
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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.

Popular places to visit in Winter Park

Image for Casa Feliz Historic Home Museum

Casa Feliz Historic Home Museum

You can spend time exploring the galleries in Casa Feliz Historic Home Museum during your travels in Winter Park. Wander the area's college campus or simply enjoy one of its top-notch restaurants.

Casa Feliz Historic Home Museum
Image for Kraft Azalea Gardens

Kraft Azalea Gardens

Explore the great outdoors at Kraft Azalea Gardens, a lovely green space in Winter Park. Stroll along the area's lakeside or experience its great live music.

Kraft Azalea Gardens
Image for Albin Polasek Museum and Sculpture Gardens

Albin Polasek Museum and Sculpture Gardens

Tour the historic home and lakeside gardens of a prominent 20th-century sculptor, and see some of his most important creations.

Albin Polasek Museum and Sculpture Gardens

Frequently asked questions