Choose from 1,527 vacation rentals located in Windsor Hills, Florida. Top filters in Windsor Hills include Air conditioner, Kitchen / Kitchenette, and Pool. Prices range from $65 to $2,181 per night. Our most popular vacation rental types near Windsor Hills are Hotel and RV.

Top vacation rentals in Windsor Hills

The lanai has a table that seats 8, privacy bushes, 4 lounge chairs & BBQ
5.0
Outstanding(284 Reviews)
House
 in Kissimmee
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
14 guests · 6 bedrooms · 4 baths
Garden · Pool · Pets allowed

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Windsor Hills, at $377 per night for your next great vacation.

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Spectacular pool views from the condo and balcony.  Disney themed throughout
5.0
Outstanding(259 Reviews)
Condo
 in Kissimmee
Poolside: Disney themed with Spectacular Pool & Water park views
8 guests · 3 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

Nestled in Windsor Hills, this Condo is perfect for your next vacation. Enjoy Poolside: Disney themed with Spectacular Pool & Water park views's top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

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Property view
4.5
Excellent(29 Reviews)
Villa
 in Orlando
Olivia's Dream Villa on WindsorHills
Garden · Pool · Kitchen / Kitchenette

This Villa for $171 in Windsor Hills, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Property view
4.7
Outstanding(65 Reviews)
Condo
 in Orlando
DREAM Vacation BY A3G
Pool · Kitchen / Kitchenette · Air conditioner

Looking to create some memories in Windsor Hills? Look no further than our Condo, DREAM Vacation BY A3G. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

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Search by amenity

Vacation rentals with air conditioning in Windsor Hills

Air Conditioned Game Room - Billiards, Pinball, Multi-Arcade, Bubble Hockey
5.0
Outstanding(189 Reviews)
House
 in Kissimmee
Villa Sonrisa - 5 Bedroom\/5 Bath Luxury, Minutes To Disney In Windsor Hills
10 guests · 5 bedrooms · 5 baths
Garden · Pool · Kitchen / Kitchenette

When traveling to Windsor Hills, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $303 per night.

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Living area
4.9
Outstanding(199 Reviews)
Condo
 in Kissimmee
🏝New Water Park!!! Huge Pool, 5 Minutes to Disney World!🏝
5 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen / Kitchenette

Looking to create some memories in Windsor Hills? Look no further than our Condo, 🏝New Water Park!!! Huge Pool, 5 Minutes to Disney World!🏝. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

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Welcome to our beautiful townhome, located just 2 miles from Disney World!
4.9
Outstanding(176 Reviews)
House
 in Kissimmee
⭐⭐⭐⭐⭐Luxury for You, Fun for the Kids! 3BR\/3BA 2 Miles from Disney
8 guests · 3 bedrooms · 3 baths
Pool · Kitchen / Kitchenette · Air conditioner

Experience vacation in Windsor Hills with our House, ⭐⭐⭐⭐⭐Luxury for You, Fun for the Kids! 3BR\/3BA 2 Miles from Disney. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

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Welcome to our Villa Front view from street.
4.8
Outstanding(212 Reviews)
House
 in Kissimmee
10% OFF ⭐⭐⭐⭐⭐ Top Rated Disney Adventure Villa Luxury Home Windsor Hills Resort
14 guests · 6 bedrooms · 4 baths
Garden · Pool · Kitchen / Kitchenette

Indulge in a peaceful retreat at 10% OFF ⭐⭐⭐⭐⭐ Top Rated Disney Adventure Villa Luxury Home Windsor Hills Resort, our elegant House in Windsor Hills. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

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Windsor Hills

Windsor Hills travel guide

Let us help you plan your perfect Windsor Hills vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Windsor Hills, and more.

Frequently asked questions

What are the most popular vacation rental amenities in Windsor Hills?

  • Air conditioner
  • Kitchen / Kitchenette
  • Pool

What are the best neighborhoods to visit in Windsor Hills, FL?

  • Windsor Hills is one of the most popular neighborhoods to visit in the Orlando area.
  • The area is known for its close proximity to Walt Disney World and its beautiful homes.
  • The top neighborhoods to visit in Windsor Hills include:
    • Emerald Island Resort
    • Windsor Palms
    • Windsor Hills Resort
    • Windsor Hills Lakeside

What are the most popular vacation rental amenities in Windsor Hills, FL?

Windsor Hills, FL is one of the most popular vacation rental destinations in the US. The area is known for its warm weather, beautiful beaches, and fun attractions. Here are some of the most popular amenities that vacationers can find in Windsor Hills:

  • Swimming pool - Many vacation rentals come with a private swimming pool, allowing visitors to enjoy some fun in the sun.
  • Fitness center - Amenities like a fitness center or gym can help vacationers stay active during their stay.
  • Game room - Game rooms are a great amenity for families looking for some fun, indoors or outdoors.
  • Air conditioning - Last, but certainly not least, having access to air conditioning is a must for any vacation rental in Florida.

What are the must-visit tourist attractions in Windsor Hills, FL?

Windsor Hills, FL is a great destination for tourists looking to experience the beauty of Florida. Here are some of the must-visit attractions in the area:

  • Disney’s Animal Kingdom
  • Walt Disney World Resort
  • Universal Studios Florida
  • SeaWorld Orlando

These attractions offer a variety of activities for people of all ages. From thrilling roller coasters and animal encounters to interactive shows and educational experiences, there is something for everyone to enjoy in Windsor Hills, FL.

How can I get around in Windsor Hills, FL?

You can get around Windsor Hills, FL in a variety of ways:

  • By car or public transportation
  • By bike or on foot
  • Through carpooling or ride-sharing services

Where can I find affordable accommodation in Windsor Hills, FL?

Windsor Hills, Florida offers a variety of affordable accommodations to suit any budget. From cozy bed and breakfasts to extended stay hotels, guests can find the perfect place to stay in this vibrant area. Here are a few of the top options:

  • Paradise Palms Resort: A luxurious resort with modern amenities, perfect for families or larger groups.
  • Vista Cay Resort: A 4-star resort offering one- and two-bedroom suites and a host of amenities.
  • Rosen Inn: An affordable hotel located close to Orlando attractions, ideal for budget-conscious travelers.
  • Hawthorn Suites: A comfortable extended stay hotel with fully-equipped kitchens and other amenities.

What is the culture like in Windsor Hills, FL?

Windsor Hills, FL is a vibrant community with a unique culture that is both inviting and engaging. Residents of the area enjoy a variety of activities and events that bring them together throughout the year. Here are 5 elements of the culture in Windsor Hills, FL:

  • Community events such as the annual Christmas parade and the monthly food truck nights.
  • A strong sense of community pride, with residents coming together to help their neighbors in times of need.
  • A commitment to preserving the local environment, with many residents participating in local clean-up days.
  • A supportive small business culture, with many local businesses hosting events and contributing to the community.
  • An inclusive atmosphere, with residents of all backgrounds celebrating their differences and coming together as one.

Is Windsor Hills, FL safe to travel to?

Windsor Hills, FL is a safe place to travel to. Here are a few reasons why:

  • Low crime rate
  • Friendly locals
  • Plenty of activities to do

You'll be sure to have a great time in Windsor Hills, FL!

What are the popular shopping destinations in Windsor Hills, FL?

Windsor Hills, FL is a popular shopping destination with many stores to choose from. Here are some of the most popular places to shop:

  • Walmart Supercenter
  • Target
  • Publix Super Market
  • Kohl's

Where is Windsor Hills, FL?

Windsor Hills, FL is a census-designated place located in Osceola County, Florida. It is located just south of the Walt Disney World Resort and is a popular destination for tourists and vacationers. Windsor Hills is home to many attractions, including a community pool, a fitness center, and a movie theater.

What are the top things to do in Windsor Hills, FL?

Windsor Hills, FL is a great place to visit, with plenty of fun activities for everyone. Here are the top things to do in Windsor Hills:

  • Visit the Disney World Resort
  • Explore the Universal Studios Theme Park
  • Go on a shopping spree at the Florida Mall
  • Take a relaxing stroll through the Harry P. Leu Gardens
Whether you're looking for a fun day out with the family or a relaxing day to yourself, Windsor Hills has something for everyone.

What do I need to know before visiting Windsor Hills, FL?

Before visiting Windsor Hills, FL, it is important to know the following:

  • The area is a popular destination for tourists
  • The climate is generally warm and humid
  • The area is home to a variety of outdoor activities, including golfing, swimming, and fishing

It is also important to be aware of local laws and regulations, as well as any potential safety concerns. Additionally, visitors should be prepared for the cost of living in the area, as prices may be higher than in other parts of the state.

What is the price range for rentals in Windsor Hills?

Vacation rentals in Windsor Hills have a price range between $65-$2,181. The average price for rentals in Windsor Hills is $199 per night.

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