Windsor Hills, FL

Orlando

USA, Florida, Celebration, Palm Trees
Orlando, Florida. July 22, 2019 Orlando gold lettering on black background. Vector with travel icons and fireworks. Travel Postcard

Popular places to visit

Walt Disney World® Resort

Walt Disney World® Resort

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

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

Universal Studios Florida
Universal Orlando Resort

Universal Orlando Resort

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

Universal Orlando Resort
Disney Springs™

Disney Springs™

Families have everything they could want in an area where boredom is absent and plenty of shopping and dining experiences are available.

Disney Springs™
Magic Kingdom® Park

Magic Kingdom® Park

One of the most famous theme parks in the world offers a land of fun and fantasy at the foot of a fairytale castle.

Magic Kingdom® Park
Orange County Convention Center

Orange County Convention Center

Florida's principal convention center is a large and stunning glass and metal building that hosts national and international trade shows and public events.

Orange County Convention Center

Things to do

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
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$192
per traveler
80% of travellers recommend
Universal Orlando Resort Express Passes
Andretti Indoor Karting & Games in Orlando

Andretti Indoor Karting & Games in Orlando

$31
per adult
90% of travellers recommend
Andretti Indoor Karting & Games in Orlando
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
Orlando: Chocolate Kingdom Factory Adventure Tour

Orlando: Chocolate Kingdom Factory Adventure Tour

$24
per adult
100% of travellers recommend
Orlando: Chocolate Kingdom Factory Adventure Tour
See all activities in Orlando

Windsor Hills Hotel Deals

Steps from Waterpark/Pool. Next to Disney w/ Frozen, Aladdin, Beauty&Beast theme

Steps from Waterpark/Pool. Next to Disney w/ Frozen, Aladdin, Beauty&Beast theme

Kissimmee FL
$336 nightly
The price is $376 total per night from May 13 to May 14
$376 total
May 13 - May 14
Total with taxes and fees
Book a stay at this family-friendly condo in Kissimmee. Enjoy free WiFi, a fitness center, and laundry facilities. Our guests praise the pool and the helpful ...
10/10 Exceptional! (232 reviews)
Absolutely perfect little vacation home… clean and super cute! Our kids loved their rooms and the decor added a special touch for our Disney trip. The owners were very responsive and helpful with all of our questions… would definitely recommend to others and stay here again!

Reviewed on Mar 17, 2026

Steps from Waterpark/Pool. Next to Disney w/ Frozen, Aladdin, Beauty&Beast theme
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
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy private pools, a fitness center, and a garden. Our guests praise the helpful staff in our ...
9.4/10 Exceptional! (259 reviews)
Accommodation was perfect for our group, pool was great after long days and community is very clean and quiet. Very close to anything you could possibly need for grocery and entertainment. Would recommend and stay in Windsor Hills again.

Reviewed on Apr 19, 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
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a garden. Popular attractions Disney's Animal Kingdom® Theme ...
9.6/10 Exceptional! (77 reviews)
Property was clean and as described. Management company came by one day to change filters and was pleasant to talk to. All messages were quickly responded to. A few notes to make the stay more comfortable: Add more pool towels (only a few were available which was fine because we brought some), Add ...

Reviewed on Apr 6, 2026

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Fun for kids and parents 6BR/4BA with private pool & hot tub in resort community
Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5

Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5

Kissimmee FL
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Disney's Animal Kingdom® ...
10/10 Exceptional! (82 reviews)
The game room was a huge hit for the kids, the pool being heated was helpful (a cold front dipped temperatures right before our stay). Plenty of towels and linens available. Great/fast communication with the host. Easy check out/clean up. Community clubhouse pool area is fun place to hang too.

Reviewed on Mar 22, 2026

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Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear

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

Kissimmee FL
$541 nightly
The price is $605 total per night from May 18 to May 19
$605 total
May 18 - May 19
Total with taxes and fees
Book a stay at this family-friendly vacation home in Kissimmee. Enjoy free WiFi, private pools, and a fitness center. Our guests praise the pool and the helpful ...
10/10 Exceptional! (373 reviews)
Everything was perfect! Host was excellent at providing all the information ahead of time. House had essentials that made our vacation so much easier.

Reviewed on Apr 18, 2026

Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
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
Book a stay at this golf villa in Kissimmee. Enjoy free WiFi, private pools, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
10/10 Exceptional! (195 reviews)
Our family (four adults, 2 & 3.5 year olds) had a fantastic time at this home. This is the second house we’ve rented in the Windsor Hills community and we absolutely love the great playgrounds, the café at the pool and the proximity to Disney property. All communication leading up to our stay was ...

Reviewed on Mar 30, 2026

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Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
See all 1,825 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.

Other neighborhoods around Windsor Hills

Sunset at the Twin Oaks Conservation Area near Kissimmee, Florida.

Orange Lake

While visiting Orange Lake, you might make a stop by sights like Walt Disney World® Resort and Orange Lake Golf.

Orange Lake
Bahama Bay

Bahama Bay

While visiting Bahama Bay, you might make a stop by sights like Northeast Regional Park and Lake Davenport.

Bahama Bay
Reunion

Reunion

The waterparks and pristine golf courses are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

Reunion
Big live oak tree draped in moss, St. Cloud, Florida.

Champions Gate

Abundant dining options and pristine golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.

Champions Gate
A panoramic shot of an egret flying low over a lake in Celebration, Florida, giving the illusion of there being three separate birds.

Highlands Reserve

4/5(22 area reviews)

While Highlands Reserve isn't home to many top sights, Highland Reserve Golf Club and Northeast Regional Park are some notable places to visit nearby.

Highlands Reserve
Kissimmee Florida aerial view

Regal Palms

3.5/5(12 area reviews)

While Regal Palms isn't home to many top sights, Highland Reserve Golf Club and Northeast Regional Park are some notable places to visit nearby.

Regal Palms
See our Where To Stay guide

Windsor Hills, FL

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