Windsor Hills Vacation Packages 2026 from $280

Windsor Hills flight + hotel vacation packages

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

Westgate Towers Resort

$280

per person

Jan 6 - Jan 10

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) 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.

Disney's Animal Kingdom Lodge

Bay Lake

$1,732

per person

Dec 21 - Dec 26

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

$399

per person

Jan 11 - Jan 16

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Orlando (MCO)

This hotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.

Westgate Lakes Resort & Spa Universal Studios Area

$362

per person

Dec 14 - Dec 19

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.

Westgate Cocoa Beach Resort

Save 100% on your flight

$846

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Detroit (DTW) 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.

Top Windsor Hills hotels deals

Kissimmee Resort Villa, 4 Bed / 4 Bath En-Suite, Heated South Pool & AC Arcade

Kissimmee FL

Get rates

This villa features an outdoor pool and a gym. Families will appreciate the arcade/game room and barbecue grills. A hot tub and laundry facilities are also provided.

Pool

Hot Tub

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

Kissimmee FL

Get rates

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

Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!

Kissimmee FL

Get rates

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 hot tub and a garden are also provided.

Pool

Hot Tub

Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Kissimmee FL

Get rates

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

Pool

Hot Tub

Newly Totally Renovated-Video Game Room-Private Pool

Kissimmee FL

Get rates

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

Pool

Hot Tub

Hidden Gem Resort Community Close to DISNEY!; 3BR/2BA w/ Water Park.

Kissimmee FL

Get rates

This condo 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 is also provided.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Windsor Hills

View all properties

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 $280. 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.