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Winter Park Vacation Packages

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A clock with 'Winter Park' and 'Central Park' inscribed, surrounded by lush greenery and trees.

Winter Park
Orlando
Florida
United States of America
North America
Hotwire.com

Winter Park Flight + Hotel Packages

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

Seasons Florida Resort

2 out of 5

Save 100% on your flight

Price was $269, price is now $137 per person

$137

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Orlando (MCO)

Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.

Me gusto está bien localizado y el precio super

Reviewed on Aug 28, 2026

Palazzo Lakeside Hotel

3 out of 5

Price was $1,303, price is now $592 per person

$592

per person

Nov 6 - Nov 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.

For the price paid this hotel was way beyond expectations. It was clean, modern, great facilities! The lake was lovely, the pool great with the movies showing at night. Be aware of the resort fee you need to pay each night which is $30+ we only stayed for one night so not bad.. breakfast is also great and included in the price. We enjoyed our time here

Reviewed on Aug 28, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5

Price was $1,157, price is now $570 per person

$570

per person

Oct 1 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Orlando (MCO)

Stay at this hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and Disney's Hollywood Studios® are located nearby.

Westgate Cocoa Beach Resort

4 out of 5

Price was $1,968, price is now $969 per person

$969

per person

Oct 7 - Oct 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Orlando (MCO)

Book a stay at this family-friendly aparthotel in Cocoa Beach. Enjoy free parking, free water park access, and a lazy river. Our guests praise the helpful staff in our reviews. Popular attractions Cocoa Beach and Ron Jon Surf Shop are located nearby.

over priced room poor concierge services poor food selección at the bar super early check out time

Reviewed on Aug 23, 2026

Westgate Palace Hotel / Universal / I-Drive

4 out of 5

Save 100% on your flight

Price was $1,214, price is now $606 per person

$606

per person

Oct 8 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

Book a stay at this family-friendly resort in Orlando. Enjoy free WiFi, free parking, and a free theme park shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye are located nearby.

Staff was very friendly and informative. Location was great. I will be staying here again.

Reviewed on Aug 25, 2026

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5

Price was $418, price is now $218 per person

$218

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Orlando (MCO)

Stay at this hotel in Orlando. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and Universal’s Islands of Adventure are located nearby.

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5

Save 100% on your flight

Price was $391, price is now $207 per person

$207

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Orlando (MCO)

Book a stay at this spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Orange County Convention Center and The Orlando Eye are located nearby.

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5

Save 100% on your flight

Price was $805, price is now $448 per person

$448

per person

Nov 17 - Nov 22

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Book a stay at this family-friendly hotel in Orlando. Enjoy free parking, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Orlando Vineland Premium Outlets and Disney Springs™ are located nearby.

Nice property overall. I love the fact that you have balconies, and individual washer and dryers in the unit. However, I do not like how you say there's a $50 deposit but you charge $100?

Reviewed on Aug 25, 2026