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Winter Garden Vacation Packages

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A brick building with a clock tower and a sign that reads "Winter Garden."

Winter Garden
Florida
United States of America
North America
Hotwire.com

Winter Garden Flight + Hotel Packages

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

Seasons Florida Resort

2 out of 5

Price was $327, price is now $136 per person

$136

per person

Oct 23 - Oct 27

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.

Lo recomiendo 100% nos gusta mucho ya nos hemos hospedado varias veces y siempre nos hemos ido con una buena impresión desde el estacionamiento limpio cuartos limpios se descansa muy bien bien silencioso y todo accesible desde restaurantes hasta comercios

Reviewed on Aug 12, 2026

Westgate Towers Resort

3.5 out of 5

Price was $636, price is now $256 per person

$256

per person

Oct 25 - Oct 31

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Orlando (MCO)

Book a stay at this family-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.

Westgate Palace Hotel / Universal / I-Drive

4 out of 5

Price was $1,394, price is now $579 per person

$579

per person

Oct 28 - Nov 4

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.

Palazzo Lakeside Hotel

3 out of 5

Price was $405, price is now $178 per person

$178

per person

Oct 14 - Oct 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Todo céntrico, me encantó

Reviewed on Aug 12, 2026

Westgate Vacation Villas Resort

4 out of 5

Save 100% on your flight

Price was $348, price is now $155 per person

$155

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Orlando (MCO)

Book a stay at this family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.

The Delaney Hotel

3.5 out of 5

Price was $704, price is now $331 per person

$331

per person

Oct 23 - Oct 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Orlando (MCO)

Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the bar in our reviews. Popular attractions Kia Center and Florida Mall are located nearby.

Westgate Town Center Resort

4 out of 5

Save 100% on your flight

Price was $864, price is now $476 per person

$476

per person

Nov 4 - Nov 9

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

Book a stay at this family-friendly resort in Kissimmee. Enjoy free WiFi, free parking, and 14 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are located nearby.

The Water park wasn't included.

Reviewed on Aug 12, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5

Save 100% on your flight

Price was $892, price is now $508 per person

$508

per person

Oct 9 - Oct 12

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.

Absolutely great place to stay. No complaints. Our condo had everything we needed. A beautiful place to stay and free access daily to the water park was awesome. Plenty of places to eat and shop super close to the resort. A definite smart choice way better than a hotel. Making plans with friends for the next trip.

Reviewed on Aug 10, 2026