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Windsor Hills Resort, Kissimmee, Florida, United States of America

Windsor Hills Resort vacation rentals

We found 1,279 vacation rentals — enter your dates for availability

Discover a selection of 1,500 vacation rentals in Windsor Hills Resort that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including private pools and swimming pools. Prices start at $93 per night, and houses and condos are popular options for a stay in Windsor Hills Resort. Either way, you'll find a rental for everyone's needs.
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Houses

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Condos/Apartments

View 258 Condos/Apartments

Villas

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Townhouses

View 238 Townhouses

Studios

View 24 Studios

Find the best place to stay — Windsor Hills Resort

Magical 4 Bedroom Villa with Private Pool Minutes from Disney! Free Pool Heat!

Sleeps 8 · 4 Bedrooms · 4 Bathrooms
$263 avg/night
(20)

🌴WindsorHills*Disney 2.5 miles*3b/3b*5-star Resort *end unit*updated🌴

Sleeps 8 · 3 Bedrooms · 3 Bathrooms
$118 avg/night
(80)

Amazing Villa - Saltwater Pool, ⚡ Fast WiFi, HVAC UV Lights & Game Room

Sleeps 14 · 6 Bedrooms · 4 Bathrooms
$383 avg/night
(175)

*ALL BRAND NEW* SOUTH POOL & Spa w/FREE HEAT-6Bed/4B RESORT-home/2.5Miles-DISNEY

Sleeps 12 · 6 Bedrooms · 4 Bathrooms
$275 avg/night
(31)

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

Sleeps 12 · 6 Bedrooms · 4 Bathrooms
$300 avg/night
(83)

Fully Remodeled~Windsor Hills~2.5 Miles from Disney World Main Entrance

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
$110 avg/night
(50)

Search 1,279 vacation rentals

Top rated rentals — Windsor Hills Resort
Stayed Apr 2021

Perfect Offsite Disney Condo

Run don’t walk to this condo if you are looking for a place to stay while visiting Orlando! This condo is perfect!!!! Spotless and spacious and close to everything you need!!! Not to mention the resort style pool on site! We will be back for sure!!! ...

HALEY W.
HALEY W.
Stayed Apr 2021

Our favorite house on VRBO

We love this house and location of this house to everything, WDW and a Walmart just down the rode . We stayed here in 2016 and will be back again ! This house is always clean and quiet . We have never had a problems at this property and the swimming ...

JIM C.
JIM C.
Stayed Apr 2021

Great Home

We had an amazing stay. The house was everything the pictures portrayed. During the stay there was an issue with the cable and WiFi, we contacted the company and it was addressed the same evening. We loved the convenience of the pool and spa. We spen...

January R.
January R.
Stayed Apr 2021

A perfect vacation spot!

Our family stayed for a little over a week and had a blast! The kids loved the game room so much that they keep asking for one at home now too. Our family of 5 fit comfortably with lots of extra space to spare. The house is clean, comfortable, well d...

Cheryl Z.
Cheryl Z.
Stayed Apr 2021

An amazing property!

We opted to stay here instead of on-site for a short Disney trip and would definitely be back! The house was fully stocked with everything we needed, was very clean and in a great corner lot location. The travel to Disney was quick and traffic was no...

Molly K.
Molly K.
Stayed Apr 2021

Great place for everything

Our experience was genuinely 5-star. The house is exactly as described and then some. The pool is perfect for all ages and kept nicely warm (I'm a wimp and hate cold pools). Great indoor and outdoor spaces for eating, relaxing, and handles multiple f...

Gordy W.
Gordy W.
Stayed Apr 2021

Spacious and clean, perfect for families

My family had a wonderful experience staying at this rental property. The villa was freshly cleaned, well decorated, and larger than I expected based on the photos. My children thoroughly enjoyed the pool and game room, as well as the community ameni...

Christine J.
Christine J.
Stayed Apr 2021

Daughter’s Cheer Competition

Property owner was very friendly even with my chaotic stay. This was my first time using a VRBO and wasn’t very knowledgeable about some of the rules. He was still able to accommodate my family and was very professional. The house was AMAZING, I woul...

Jessica H.
Jessica H.
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How many vacation rentals are available around Windsor Hills Resort?

Our 2021 property listings offer a large selection of 1,279 vacation rentals around Windsor Hills Resort. From 1,021 house rentals to 258 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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