Windsor Hills Vacation Packages 2025/2026 from $242

Windsor Hills flight + hotel vacation packages

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

Palazzo Lakeside Hotel

Save 100% on your flight

$242

per person

Dec 8 - Dec 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool, a gym, and a restaurant. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

Vilano Beach

$391

per person

Jan 8 - Jan 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

The private beach and full-service spa are among the highlights at this hotel. Relax with beach cabanas, sun loungers, and beach umbrellas. Enjoy the outdoor pool and free perks like buffet breakfast and WiFi in public areas.

Westgate Cocoa Beach Resort

$1,493

per person

Dec 25 - Jan 1

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 condo resort. 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.

Alhambra Villas

Solivita

Save 100% on your flight

$275

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

This hotel features an outdoor pool and an outdoor tennis court. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. WiFi in public areas is free.

Bryan’s Spanish Cove

Save 100% on your flight

$353

per person

Dec 8 - Dec 15

found 3 hours ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

An outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and concierge services are also on offer.

Top Windsor Hills hotels deals

6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ

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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 families will appreciate the onsite laundry facilities. Enjoy the gym and conveniences like a garden and barbecue grills.

Pool

Hot Tub

2 Bedroom, 2 Bath Condo 2 miles from Disney and 10 miles from Universal studios.

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A water park and an outdoor pool are featured at this smoke-free condo. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A gym, a hot tub, and a garden are also on offer.

Pool

Hot Tub

Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5

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A water park and an outdoor pool are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A gym, a hot tub, and barbecue grills are also on offer.

Pool

Hot Tub

🌴Beautiful home in Windsor Hills Resort -Disney 2.5 miles 🌴

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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 garden is also provided.

Pool

Kitchen

Our DisneyDreamVilla - minutes to DisneyWorld!!!

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A water park and an outdoor pool are featured at this smoke-free villa. 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

Be our Guest - 3 bedroom, sleeps 7 + Condo w/ pool view by Disney and Universal

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A water park and a hot tub are featured at this smoke-free condo. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free WiFi.

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

Walt Disney World® Resort

4.5/5(2,427 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.

Universal Studios Florida

4.5/5(9,273 reviews)

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

Universal Studios Orlando showing street scenes, a city and rides

Universal Orlando Resort

4.5/5(4,155 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 $242. 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.