Windsor Hills Vacation Packages 2026 from $507

Windsor Hills flight + hotel vacation packages

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

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$507

per person

Nov 17 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

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.

Disney's Animal Kingdom Lodge

Bay Lake

$1,602

per person

Dec 14 - Dec 19

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

A full-service spa, 3 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. There's fun for all ages with a children's club and a theme park shuttle, and families will appreciate the onsite laundry facilities. Traveling on business? Take advantage of the express check-in, express check-out, and valet parking.

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$1,014

per person

Dec 21 - Dec 27

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

Save 100% on your flight

$545

per person

Nov 30 - Dec 6

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

🌴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.

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

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.

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.

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.

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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 $507. 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.