Windsor Hills Vacation Packages 2026 from $403

Windsor Hills flight + hotel vacation packages

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

Seasons Florida Resort

Save 100% on your flight

$403

per person

Jun 28 - Jul 5

found 1 day ago

Roundtrip non-stop 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.

Westgate Town Center Resort

Save 100% on your flight

$514

per person

Jun 27 - Jul 4

found 1 day ago

Roundtrip non-stop 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.

Westgate Vacation Villas Resort

Save 100% on your flight

$517

per person

Jun 27 - Jul 4

found 8 hours ago

Roundtrip non-stop 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

$500

per person

Jun 27 - Jul 4

found 8 hours ago

Roundtrip non-stop 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 Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$598

per person

Jul 26 - Aug 1

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.

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.

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.

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.

2 Miles to Disney - 20 sec Walk to Clubhouse - Private Pool - Free Water Park

Kissimmee FL

$368 nightly

$411 total

May 30 - May 31

Total with taxes and fees

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. Enjoy the hot tub and perks like free WiFi.

Dream Disney Family Vacation,one of best resort 2 miles to Disney, space for 8

Kissimmee FL

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

Disney Retreat in Windsor Hills Resort

Four Corners FL

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A gym is featured at this apartment, along with 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.

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 $403. 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.