Windsor Hills Vacation Packages 2026 from $322

Windsor Hills flight + hotel vacation packages

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

Seasons Florida Resort

$322

per person

Jan 7 - Jan 12

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.

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

$1,003

per person

Jan 15 - Jan 22

found 1 day 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

$503

per person

Jan 7 - Jan 12

found 1 day ago

Roundtrip non-stop 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.

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

$399

per person

Jan 11 - Jan 16

found 16 hours 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.

Disney's Animal Kingdom Lodge

Bay Lake

$1,408

per person

Dec 16 - Dec 20

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.

Top Windsor Hills hotels deals

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

Kissimmee FL

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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

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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. 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

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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 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

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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

Newly Totally Renovated-Video Game Room-Private Pool

Kissimmee FL

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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

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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

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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 $322. 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.