Windsor Hills Vacation Packages 2026 from $259

Windsor Hills flight + hotel vacation packages

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

Westgate Town Center Resort

Save 100% on your flight

$259

per person

Nov 19 - Nov 23

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) 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 mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.

Westgate Towers Resort

$355

per person

Dec 2 - Dec 9

found 15 hours ago

Roundtrip flight included

Chicago (ORD) to Orlando (MCO)

2 outdoor pools, 2 hot tubs, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

The Delaney Hotel

South Orange

Save 100% on your flight

$821

per person

Nov 20 - Nov 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a terrace, and a snack bar/deli are also offered.

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$601

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Free water park access, 4 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. You'll appreciate the hot tub, poolside bar, and snack bar/deli.

Seasons Florida Resort

$309

per person

Oct 16 - Oct 19

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and laundry facilities are also provided.

Top Windsor Hills hotels deals

Newly Totally Renovated-Video Game Room-Private Pool

Kissimmee FL

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This vacation home features an outdoor pool and a gym. A hot tub and laundry facilities are also provided.

Pool

Hot Tub

6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ

Kissimmee FL

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This vacation home features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A garden and barbecue grills are also provided.

Pool

Hot Tub

🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴

Kissimmee FL

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This vacation home features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A garden is also provided.

Pool

Kitchen

Fabulous Lake View/South Facing Pool Home- Game room -2 Miles to Disney!

Kissimmee FL

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This vacation home features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A garden and barbecue grills are also provided.

Pool

Hot Tub

Mickey Mouse Farmhouse-Fully Upgraded Condo in Windsor Hills. 2 Miles to Disney!

Kissimmee FL

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This condo features an outdoor pool and a gym. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the hot tub and perks like free WiFi.

Pool

Hot Tub

Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear

Kissimmee FL

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This vacation home features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the hot tub and conveniences like a garden and laundry facilities.

Pool

Hot Tub

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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.

Frequently asked questions

How much are vacation packages to Windsor Hills?

With Travelocity vacation packages, you can live it up in Windsor Hills for a mere $259. Flights, hotels and tours — we have it all. You'll save loads just for bundling your bookings. With everything taken care of before you go, you can sit back, relax and not worry about a thing.

Where can I get the best vacation package deals for Windsor Hills?

It's difficult to beat Travelocity when it comes to putting together your Windsor Hills package deal. There are as many as 400 airlines and 1,000,000 worldwide properties to select from. Reserve your trip now and get ready to tick another place off your must-visit list.

Why should I purchase my Windsor Hills vacation package with Travelocity?

Incredible savings, loads of thrilling destinations and 24/7 customer service you can rely on — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always get the best possible deal with Travelocity.

Can I save on my Windsor Hills car rental if I bundle it with hotels and flights?

Sure can — and if you also add a tour or an experience to your Windsor Hills vacation package, you'll pick up even more savings. With an affordable package from Travelocity, you can find things to do in the region that are just right for you. Then, jump in your rental car and work your way through the list. Daytona International Speedway is one must-see sight to key into your GPS. It's 70 mi from Windsor Hills.