Windsor Hills Vacation Packages 2026 from $294

Windsor Hills flight + hotel vacation packages

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

Westgate Vacation Villas Resort

Save 100% on your flight

$294

per person

May 3 - May 9

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 Towers Resort

Save 100% on your flight

$309

per person

May 3 - May 9

found 1 day ago

Roundtrip flight included

Boston (BOS) 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 Town Center Resort

Save 100% on your flight

$316

per person

Apr 26 - Apr 30

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

Florida Hotel & Conference Center in the Florida Mall

Save 100% on your flight

$832

per person

May 18 - May 25

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This traditional aparthotel includes 3 restaurants, an outdoor pool, and a gym. Bring the family and enjoy the free theme park shuttle and kid-friendly dining. Enjoy the hot tub and perks like free WiFi.

Seasons Florida Resort

Save 100% on your flight

$407

per person

Jun 4 - Jun 11

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

Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!

Kissimmee FL

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This condo features an outdoor pool and a gym. Laundry facilities are provided for your convenience.

Pool

Kitchen

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

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 hot tub and barbecue grills are also provided.

Windsor Hills Private Luxury Pool House, Sleeps 13

Kissimmee FL

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This villa 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. Enjoy the hot tub and conveniences like a garden and concierge services.

Steps from Waterpark/Pool. Next to Disney w/ Frozen, Aladdin, Beauty&Beast theme

Kissimmee FL

$423 nightly

$473 total

Mar 27 - Mar 28

Total with taxes and fees

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. Barbecue grills are provided for your convenience.

Hot Tub

Kitchen

Disney Retreat in Windsor Hills Resort

Four Corners FL

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A gym is featured at this condo, along with laundry facilities.

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

Kissimmee FL

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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.

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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.

Popular places to visit

Walt Disney World® Resort

Have a fun-filled day at Walt Disney World® Resort and find out why this is a popular theme park in Lake Buena Vista. Discover the top-notch restaurants and acclaimed theater scene in this walkable area.

Universal Studios Florida

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Orlando Resort

Have a fun-filled day at Universal Orlando Resort and see why people love this theme park in Orlando. Check out the shops and top-notch restaurants in this family-friendly area.

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 $294. 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.