Windsor Hills Vacation Packages 2026 from $457

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

$457

per person

Aug 27 - Sep 1

found 2 days 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.

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$865

per person

Aug 27 - Sep 1

found 2 days 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.

The Delaney Hotel

South Orange

Save 100% on your flight

$531

per person

Aug 27 - Sep 1

found 2 days ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a terrace, and a snack bar/deli are also offered.

WorldQuest Orlando Resort

Save 100% on your flight

$539

per person

Sep 20 - Sep 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

This aparthotel features an outdoor pool and a 24-hour gym. Families will appreciate the free theme park shuttle and onsite laundry facilities. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi.

Reunion Resort & Golf Club

Reunion

Save 100% on your flight

$697

per person

Sep 20 - Sep 25

found 1 day ago

Roundtrip non-stop 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

Villa 2655 - 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.

Pool

Hot Tub

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

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

Kissimmee FL

$537 nightly

$600 total

Jul 12 - Jul 13

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 barbecue grills are available on site. Enjoy the hot tub and conveniences like a garden and laundry facilities.

Pool

Hot Tub

Townhome with lots of Amenities

Kissimmee FL

$436 nightly

$487 total

Jul 28 - Jul 29

Total with taxes and fees

This vacation home features a gym and a hot tub. Families will appreciate the playground and barbecue grills. A garden and laundry facilities are also provided.

Pool

Hot Tub

Free Water Park-Walk to Clubhouse-6BR Disney Home-Sleeps 15-Private Pool & Spa

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. There's a hot tub on site, and laundry facilities and concierge services are also offered.

Pool

Hot Tub

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.

Pool

Hot Tub

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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

A castle with multiple spires and a central tower.

Walt Disney World® Resort

4.5/5(2,451 reviews)

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.

A globe with the word "UNIVERSAL" and a theme park in the background.

Universal Studios Florida

4.5/5(9,415 reviews)

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

A colorful street with various shops and a Ferris wheel.

Universal Orlando Resort

4.5/5(4,207 reviews)

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 $457. 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.