Windsor Hills Vacations

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Your Windsor Hills Vacation

Take all the hassle out of planning your next escape with a Windsor Hills vacation package. Take in the sights and sounds of this enticing neighborhood and experience all it has to offer. Eager to sightsee during your trip to Windsor Hills? Be sure to check out nearby attractions like Mystic Dunes Golf Club, Orange Lake Golf and Jack Nicklaus Course. Stop dreaming and start doing. When it's time to book your dream vacation to Windsor Hills, Expedia will help you get there.

Price found within the past 48 hours. Click for updated prices.
  • Restaurant
    Jul 21 - Jul 28

    Westgate Towers Resort + Flight

    Kissimmee
    7 nights
    3.5 star property
    8.6/10 - Excellent (1,013 reviews)
    "Very good place"
    Reviewed May 18, 2026
    Roundtrip • New York (EWR) - Orlando (MCO)
    EWR - MCO • 1 stop MCO - EWR • 1 stop
    Save 100% on your flight
    $937
    $514
    per traveler
    found 8 hours ago
    Westgate Towers Resort
  • Outdoor pool, pool umbrellas
    Jul 2 - Jul 13

    Westgate Palace Hotel / Universal / I-Drive + Flight

    International Drive District
    11 nights
    4.0 star property
    8.8/10 - Excellent (1,253 reviews)
    "Our room was extremely clean and quiet. It was very close to Universal Studios. Highly recommend!"
    Reviewed May 16, 2026
    Roundtrip • New York (EWR) - Orlando (MCO)
    EWR - MCO • 1 stop MCO - EWR • 1 stop
    $2,549
    $1,002
    per traveler
    found 1 day ago
    Westgate Palace Hotel / Universal / I-Drive
  • Water park
    Jul 21 - Jul 28

    Westgate Town Center Resort + Flight

    Kissimmee
    7 nights
    4.0 star property
    8.2/10 - Very Good (1,730 reviews)
    "This family friendly resort offers first class amenities and hospitality at a budget friendly price. The accommodations were clean and had everything we needed already there."
    Reviewed May 18, 2026
    Roundtrip • New York (EWR) - Orlando (MCO)
    EWR - MCO • 1 stop MCO - EWR • 1 stop
    Save 100% on your flight
    $1,036
    $569
    per traveler
    found 1 day ago
    Westgate Town Center Resort
  • Fountain
    Aug 4 - Aug 12

    Westgate Blue Tree Resort in Lake Buena Vista + Flight

    Orlando
    8 nights
    3.5 star property
    8.6/10 - Excellent (1,005 reviews)
    "Very few things to do but our apartment was perfect "
    Reviewed May 18, 2026
    Roundtrip • New York (EWR) - Orlando (MCO)
    EWR - MCO • Nonstop MCO - EWR • Nonstop
    Save 100% on your flight
    $1,096
    $630
    per traveler
    found 1 day ago
    Westgate Blue Tree Resort in Lake Buena Vista
  • Water park
    Jun 26 - Jul 1

    Westgate Lakes Resort & Spa Universal Studios Area + Flight

    Orlando
    5 nights
    4.0 star property
    8.4/10 - Very Good (6,490 reviews)
    "Unfortunately, my stay was disappointing. The room was very outdated and did not look well maintained. Several tiles were cracked, which made the space feel neglected and uncomfortable. Parking was also extremely limited, making it difficult to find a spot during our stay. Overall, the property did not meet expectations for the price paid."
    Reviewed May 19, 2026
    Roundtrip • New York (EWR) - Orlando (MCO)
    EWR - MCO • Nonstop MCO - EWR • Nonstop
    Save 100% on your flight
    $1,176
    $705
    per traveler
    found 2 days ago
    Westgate Lakes Resort & Spa Universal Studios Area

Where to stay in Windsor Hills

Find the best Windsor Hills areas and neighborhoods for the activities you enjoy most. Learn more about Windsor Hills
International Drive District

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

Find hotels in International Drive District

Windsor Hills Hotel Deals

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

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

Kissimmee FL
9.4/10 Exceptional! (260 reviews)
"My family and I truly enjoyed our stay at this property."

Reviewed on Apr 28, 2026

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6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community

Kissimmee FL
9.6/10 Exceptional! (78 reviews)
"The property was just as described, very spacious, clean and fully stocked. Check-in was simple and the Resort’s water park was just what we needed for a fun and enjoyable weekend. There nine people in our group and we had more than enough space to move around. I would definitely recommend this home ..."

Reviewed on Apr 27, 2026

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Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills

Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills

Kissimmee FL
10/10 Exceptional! (200 reviews)
"Great villa and so close to the parks!! Very well equipped for our family.Absolutely excellent and responsive host, helping out quickly with all our resort and other questions.A great place to stay for a family looking to “theme park”!!"

Reviewed on May 17, 2026

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Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
See all 1,815 properties in Windsor Hills
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Windsor Hills

Walt Disney World® Resort

Walt Disney World® Resort

4.5/5(2,451 reviews)

Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.

Walt Disney World® Resort
Universal Studios Florida

Universal Studios Florida

4.5/5(9,415 reviews)

Thrill rides based on your favorite movies create this internationally acclaimed theme park.

Universal Studios Florida
Universal Orlando Resort

Universal Orlando Resort

4.5/5(4,207 reviews)

Make your Florida vacation one to remember with a stay at this hotel and theme park complex.

Universal Orlando Resort

Things to do

Walt Disney World® Resort Disney After Hours

Walt Disney World® Resort Disney After Hours

$191
per adult
100% of travellers recommend
Walt Disney World® Resort Disney After Hours
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

$27
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$39
per traveler
86% of travellers recommend
LEGOLAND® Florida Tickets
See all activities in Orlando

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.