Windsor Hills Vacation Packages 2026 from $333

Windsor Hills flight + hotel vacation packages

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

Westgate River Ranch Resort & Rodeo

Save 100% on your flight

$333

per person

Oct 2 - Oct 4

found 1 day ago

Roundtrip flight included

San Juan (SJU) to Orlando (MCO)

This smoke-free resort features free water park access, a marina, and 2 restaurants. There's fun for all ages with mini golf and a playground, and barbecue grills are available on site. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking.

Westgate Towers Resort

Save 100% on your flight

$377

per person

Oct 22 - Oct 29

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) 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.

Westgate Vacation Villas Resort

Save 100% on your flight

$333

per person

Oct 30 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.

Westgate Cocoa Beach Resort

Save 100% on your flight

$728

per person

Sep 23 - Sep 27

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Orlando (MCO)

Free water park access and an outdoor pool are featured at this traditional aparthotel. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.

Reunion Resort & Golf Club

Reunion

Save 100% on your flight

$774

per person

Oct 10 - Oct 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This luxury aparthotel features a golf course, free water park access, and 7 restaurants. Bring the family and enjoy the lazy river, mini golf, and kid-friendly dining. Relax with a drink at one of the 2 poolside bars and enjoy the 11 outdoor pools and gym.

Top Windsor Hills hotels deals

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.

Magical Memories in Windsor Hills Resort

Four Corners FL

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This villa features an outdoor pool 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.

Livin the Dream❤️Closest FREE Resort to Disney! 3 Kings

Kissimmee FL

$502 nightly

$560 total

Sep 7 - Sep 8

Total with taxes and fees

A water park and a hot tub are featured at this smoke-free vacation home. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the gym and perks like free WiFi.

Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!

Kissimmee FL

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Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5

Kissimmee FL

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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 $333. 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.