Windsor Hills Vacation Packages 2026 from $408

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

$408

per person

Jul 19 - Jul 25

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.

Westgate Cocoa Beach Resort

$929

per person

Aug 22 - Aug 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Free water park access and an outdoor pool are featured at this smoke-free aparthotel. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site.

Westgate Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

$517

per person

Sep 1 - Sep 8

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.

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

Save 100% on your flight

$499

per person

Jul 20 - Jul 24

found 1 day ago

Roundtrip flight included

Boston (BOS) 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.

The Bear's Den Resort Orlando

Reunion

Save 100% on your flight

$1,839

per person

Aug 27 - Sep 2

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Orlando (MCO)

This smoke-free vacation home features a golf course, free water park access, and a restaurant. Enjoy the outdoor pool and perks like free self parking and free WiFi. You'll appreciate the gym, bar/lounge, and coffee shop.

Top Windsor Hills hotels deals

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.

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

Kissimmee FL

$543 nightly

$607 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.

To Disney, Universal & Resort fun w/ FREE water park, for adult & Children

Kissimmee FL

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

2 Miles to Disney • Walk to Clubhouse • SOUTH-FACING Pool • Free Water Park

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

Luxury Themed 6BR • Poolside Theater • Game Room

Kissimmee FL

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A water park and a hot tub are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A garden, a picnic area, and laundry facilities are also on offer.

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

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. Enjoy the hot tub and perks like free WiFi.

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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 $408. 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.