Windsor at Westside Vacation Rentals

Windsor at Westside - A Luxury Gated Vacation Rental Resort

Windsor at Westside Resort in Kissimmee, Florida is one of the newest vacation rental communities in the Orlando area. In fact, if you watch our video below, you'll see that as of December 2017, it's still being built. So, that may be a consideration if you're planning on staying there. This very impressive resort with its 10,000 sq. ft clubhouse has to be seen to be believed. On top of that, it's less than 15 minutes from Orlando Disney World® and for golfers, there are also a number of golf courses nearby.

The Facilities at Windsor at Westside Resort

Windsor at Westside Resort is a manned gated vacation rental community located 15+ minutes from Disney world and 30 minutes from Universal Studios Orlando. The impressive 10,000 sq. ft clubhouse here houses a large Resort style swimming pool and spa which sits in a large sun deck and the pool area is filled with sun loungers and other pool deck furniture. There's also a waterslide and a lazy river. Nearby there's a beach volleyball course and multipurpose court and a children's playground. Inside, the clubhouse has a large comfortable seating area, a well equipped fitness center, game room and a Tiki bar which connects the inside of the clubhouse to the pool area.

The Homes at Windsor at Westside Resort

The vacation rental homes at Windsor at Westside Resort are a combination of pool homes and two storey townhomes. In terms of bedroom numbers; the townhomes have either 4 or 5 bedrooms, while the pool homes come in a number of different configurations and so these can have 6, 7, 8 And 9 bedrooms. The homes vary in size from 2,100 to 4,400 sq. ft of air conditioned living space. All of the vacation rental homes at Windsor at Westside Resort are fully furnished to a very high standard and have upgraded kitchens with stainless steel appliances, upgraded kitchen cabinets, upgraded floor tile and granite countertops.

The homes also have upgrades elsewhere including paver driveways and walkways. The townhomes come with a splash pool and the pool homes with a full sized screened swimming pool complete with pool furniture.

Windsor at Westside on Youtube

In order to write our Central Disney Area Destination Reports, we visited each of the communities in the Orlando area and in a lot of cases we also recorded a brief video of the community and uploaded it to Youtube. We did this on our visit to Windsor at Westside, which you can see by clicking below. These videos are fairly short and are simply intended to give an impression of the community and provide potential guests with more of a feel for the neighborhood.

 
Windsor at Westside Youtube Video

Journeying from Windsor at Westside Resort to the Attractions

Many visitors come to Florida for the beaches and the year-round sunshine. But the majority come to see a certain talking mouse. Whilst it's common knowledge that the Florida Peninsula has a stunning array of natural resources, it's the man made variety that cause millions of tourists to flock to Florida and in particular, Orlando each year.

Over the past six decades, Orlando has been reinvented so as to become a world leader in mass tourism. The city's theme parks are the primary force behind that unparalleled change of fortune. Theme parks are big business in Central Florida and they're spread geographically across Orlando and south down to Tampa and are all accessible on a day trip from Windsor at Westside. But it's not just about the theme parks and attractions; if you want to take the kids surfing at Cocoa Beach on the Atlantic coast, or just feel like chilling at Clearwater Beach on the Gulf of Mexico, then either of these is achievable on a day out. Both of these beaches are no more than a 90 minute drive away.

The following driving times are approximate, but they give an indication of the convenience of staying in vacation rental home at Windsor at Westside:

Disney World® Parks - 15+ Minutes
SeaWorld - 20 Minutes
Discovery Cove - 20 Minutes
Legoland - 25 Minutes
Universal Studios - 30 Minutes
Adventure Island, Tampa - 75 Minutes
Busch Gardens, Tampa - 75 Minutes
Kennedy Space Center - 75 Minutes
Cocoa Beach - 70 Minutes
Clearwater Beach - 90 Minutes

Golfing Around Windsor at Westside

As you would expect from a destination that hangs its hat on family fun, Orlando is overflowing with casual, kid and beginner-friendly places to play golf. A golf experience here can be whatever you need it to be. If you're a beginner looking to sharpen your skills, there's a course for you, and if you're a pro looking to test your talent on a wide range of different and challenging layouts, there are several courses for you. Whatever your skillset is, Orlando offers visitors an exclusive golfing experience not found anywhere in the world. You might like to try some of the golf courses below which are near Windsor at Westside:

Ritz-Carlton Golf Club - 25 Minutes
Shingle Creek - 20 Minutes
Disney's Palm Golf Course - 15 Minutes
Lake Nona Golf and Country Club - 25 Minutes
Stoneybrook West - 25 Minutes
Waldorf Astoria - 20 Minutes
Cypresswood Golf and Country Club - 20 Minutes
Oaks National Golf Club - 20 Minutes
Cassleberry Golf Club - 35 Minutes
Hawk's Landing - 20 Minutes

Shopping and Eating near Windsor at Westside Resort

Staying at any of the communities in the Disney area means that you have literally dozens of restaurants and fast food joints on tap. So, if you want to treat the kids to dinner, then we could probably name a restaurant or two that are within a ten to fifteen minute drive of Windsor at Westside. Whilst they are largely chain restaurants, they are incredibly convenient to get to from Windsor at Westside. So, take a look through this list of eateries that are in the area, including Applebee's, Bahama Breeze, Black Angus Steak Restaurant, Bob Evans, Bonefish Grill Buffalo Wild Wings, Carrabba's Italian Grill, Charley's Steak House, Chili's, Chuy's Tex-Mex, Columbia, Cracker Barrel, Denny's, Diromio's Pizza And Grill, Five Guys, Flippers Pizza, Giordano's, Giovanni's Pizza, Golden Corral, IHOP, Joe's Crab Shack, Logan's Roadhouse, Longhorn Steakhouse, Macaroni Grill, Manny's Original Chophouse, Miller's Ale House, Olive Garden, On The Border, Outback Steakhouse, Panera Bread, Perkins, Pollo Tropical, Ponderosa, Red LobsterSizzler, Shoneys, Tarantino's Italian, Texas Roadhouse, TGI Fridays, Thai Thani, The Catfish Place and finally Zaxby's. But this list is by no means exhaustive.

If you don't feel like driving too far and just want to pick up something locally, then there's a whole range of fast food restaurants nearby which include Arby's, Burger King, Checkers, Chick-fil-A, CiCi's Pizza, Cordovano Joe's Pizza , Crown Fried Chicken, Domino's Pizza, DQ Grill and Chill, Dunkin Donuts, KFC, Long John Silver's, McDonalds, Panda Express, Papa John's Pizza, Pizza Hut, Pizzeria Uno Chicago Bar and Grill , Subway, Starbucks, Taco Bell, Upper Crust Pizza and last, but not least, Wendy's.

Supermarkets
If you're thinking of staying of an evening and cooking at home, then you'll want to find a supermarket in which to buy the food. You'll find three large supermarkets (Walmart, Publix and Target) within a five minute drive of Windsor at Westside. So, you'll never be too far away when you need to pick up a few beers and the steaks for the BBQ.

Non-Supermarket Shopping
If you're looking for something beyond supermarkets then you'll have to drive a little further. Twenty minutes down the I-4 in the Tampa direction, you'll find Posner Park where you'll find an IMAX Movie Theater and a whole range of restaurants and stores including, Books-a-Million, JC Penney, Best Buy, Staples, Target, PetSmart, DICK'S Sporting Goods.

Apparel Shopping
So, we all know that visiting the parks and lying by the pool sunbathing all day can be exhausting and so you just have to take a break from the relentless grind. So, how about a bit of retail therapy? Orlando has a wide and varied range of shops on offer that can provide some unusual shopping experiences. So, you'll need to jump in the car and head east towards Orlando. In Orlando you'll find a range of shopping options on offer. Designer brands and the latest in fashion trends are always in style at The Mall Millennia and The Florida Mall where shoppers will find top department stores offering incomparable service. Orlando's designer outlets, including Orlando Premium Outlets on International Drive, Orlando Premium Outlets on Vineland Avenue, and the Lake Buena Vista Outlets, feature a wide selection from the world's top designers at incredible savings. With this many shopping opportunities within 30 minutes driving distance, you had better bring a backup credit card.

The Climate at Windsor at Westside

The climate of the Sunshine state is influenced by the fact that all parts of the state are in close proximity to the ocean. Lake Okeechobee, in the middle of the state, is also a pivot point for the climate of Florida. Above the lake, which is where Windsor at Westside is located, the climate is classified as humid subtropical, while the areas below the lake, to the south, experience a true tropical climate.

When staying in a vacation rental in Windsor at Westside,Kissimmee, then you should plan for weather ranging from warm and pleasant from October through until May, and extremely hot between June and September. Florida sees a lot of sunshine throughout the year and the temperatures rarely fall near or below freezing (0°C / 32F).

Generally, if you visit the parks outside of the summer months, you should have a dry and comfortable experience. But in summer months, it's going to be hot and humid most days, with temperatures in the peak of summer reaching into the mid 90s F.

The rainy season arrives in May and runs on through until October. So, when leaving for the parks, you'll want to pack an umbrella and a plastic poncho, or similar. If you're a person who enjoys witnessing torrential downpours, then you can almost set your watch by the thunderstorms each afternoon during the summer month. It's also worth mentioning the Hurricane season which runs from July through to November. Fall/Autumn sees the arrival of beautiful balmy days where average temperatures and rainfall start to reduce. The winter months of December, January and February offer the coolest weather with January daytime temperatures averaging around 23°C / 73°F, but these can drop to 9°C / 48°F overnight. The driest months of the year can be found during late Fall, winter into early spring.

Alternative Communities to Consider

Windsor at Westside offers a range of good vacation rental homes and it's a convenient place to stay, but it's always worth looking at other comparable vacation rental home communities and resorts which are located within a few miles of Windsor at Westside and which might also be of interest. It's not a huge disadvantage, but the Davenport and Clermont communities are further away from most of the attractions, but they are often priced better than vacation rental homes in the Kissimmee area. In the Davenport/Clerment areas, you might want to consider Bella Toscana and also Four Corners and also Tuscan Hills which is a fantastic place to stay if you're a golfer. If you're looking to keep costs down, then check out Crescent Lakes . When it comes to vacation rental communities in Kissimmee, you may want to look at vacation rentals in Emerald Island which is close to Disney and Terra Verde , which again is close to the parks.

At roughly the same rental cost as Windsor at Westside Resort, it's worth considering Formosa Gardens, or Windsor Hills and Windsor Palms which are both full resorts and so offer more onsite entertainment.

The quality of all of the vacation rental communities around Kissimmee and Davenport is very good and the general standard of the homes in them can be exceptional. So, we would suggest that before booking any vacation home; determine your requirements including the intended travel dates and the number of adults and children in your party before contacting as many homeowners as possible. This will allow you to identify which vacation rental homes most closely suit your requirements. Whether it be availability dates, price, location, size of the property, facilities of the resort or community, etc, all of these should feature in your decision making process.

Driving Directions to Windsor at Westside

Disney World's Magic Kingdom boasts the highest attendance figures of any theme park on the planet. But Universal Orlando, which has been improving both the quality of its parks and as a consequence, its visitor numbers, is nipping at Disney's heels. So, it's little surprise that all the US domestic, and most international airlines have attempted to capitilize on this success themselves by laying busy flight schedules to Orlando. The city is served by two international airports; Orlando International Airport (MCO) and Orlando-Sanford Airport (SFB) which are 30 minutes and one hour's driving time, respectively from Windsor at Westside.

A large number of flights arrive and depart Orlando International Airport each day, with Sandford far less well served. There are a number of driving routes from Orlando International Airport to Windsor at Westside, but we generally advise on this one because of its simplicity. To reach Windsor at Westside from Orlando International Airport, take FL-417S towards Disney World® and continue until reaching the Celebration Avenue (exit #2). Keep right to take ramp towards US Highway 192 in a westerly direction. Once on Highway 192 W, drive for 6 miles and then turn left towards Westside Boulevard. After just over two miles turn Turn left onto Monaco Boulevard and the Windsor at Westside Resort will be directly ahead.

It's also worth mentioning that Highway 192 is Kissimmee's primary tourist road and so full of restaurants and shops.

Whilst our travel editors make every effort to ensure that the information contained in our Destination Reports is accurate and reliable, we take no responsibility for the validity or accuracy of the information displayed. We strongly recommend that any information shown on Tripelli.com is independently verified.

 
 

Vacation Rental Homes in or near Windsor At Westside

Sleeps 16+

$500 per night

9 Bedrooms/6 Bathrooms, 4 En-sutes 4500 sq ft,  Sleeping 24, Gym, Water park

9 Beds6 Baths4500 Sq. ft

Family Villa

( Owner Manager )

Home:
9 Beds, 6 Baths, 4500 Sq. ft, Sleeps 16+
Location:
Windsor At Westside, Florida
Features:
Air Conditioning, Swimming Pool, Hot Tub, Wifi, Satellite/Cable, Family/Kid Friendly, Games Room, No Smoking, Parks Nearby, Beach Nearby, Golf Course Nearby

Rate Info.

from $500 per night
Details
Sleeps 6

$75 per night

Windsor Hills - Stay at the Treetops - 2 BR

2 Beds2 Baths1100 Sq. ft

Condo

( Owner Manager )

Home:
2 Beds, 2 Baths, 1100 Sq. ft, Sleeps 6
Location:
Windsor Hills Resort, Florida
Features:
Air Conditioning, Swimming Pool, Hot Tub, Wifi, Satellite/Cable, Family/Kid Friendly, Games Room, No Smoking, Parks Nearby, Beach Nearby, Golf Course Nearby

Rate Info.

from $75 per night
Details
Sleeps 5

$90 per night

The Dream Villa  2 Bed

2 Beds2 Baths1583 Sq. ft

Family Villa

( Owner Manager )

Home:
2 Beds, 2 Baths, 1583 Sq. ft, Sleeps 5
Location:
Indian Ridge Oaks, Florida
Features:
Air Conditioning, Swimming Pool, Hot Tub, Wifi, Satellite/Cable, Family/Kid Friendly, Games Room, No Smoking, Parks Nearby, Golf Course Nearby

Rate Info.

from $90 per night
Details
Sleeps 6

$110 per night

3 Bed Town House at Terra Verde Restort

3 Beds3 Baths1286 Sq. ft

Family Home

( Management Company )

Home:
3 Beds, 3 Baths, 1286 Sq. ft, Sleeps 6
Location:
Terra Verde Restort, Florida
Features:
Air Conditioning, Swimming Pool, Hot Tub, Wifi, Satellite/Cable, Family/Kid Friendly, No Smoking, Parks Nearby

Rate Info.

from $110 per night
Details
Sleeps 8

$65 per night

2 Miles to Disney,1600 sqft 3BR/3BA Townhome

3 Beds2 Baths1600 Sq. ft

Family Villa

( Owner Manager )

Home:
3 Beds, 2 Baths, 1600 Sq. ft, Sleeps 8
Location:
Crestwynd Bay Community, Florida
Features:
Air Conditioning, Swimming Pool, Wifi, Satellite/Cable, Family/Kid Friendly, Games Room, No Smoking, Parks Nearby, Golf Course Nearby

Rate Info.

from $65 per night
Details
Sleeps 6

$80 per night

3 Bed Town Home 50ft from Clubhouse with Lake Views

3 Beds2 Baths1286 Sq. ft

Family Home

( Owner Manager )

Home:
3 Beds, 2 Baths, 1286 Sq. ft, Sleeps 6
Location:
Terra Verde, Florida
Features:
Air Conditioning, Hot Tub, Wifi, Satellite/Cable, Family/Kid Friendly, No Smoking

Rate Info.

from $80 per night
Details
Sleeps 6

$65 per night

Luxury Windsor Hills 3/2 Condo

3 Beds2 Baths1250 Sq. ft

Condo

( Owner Manager )

Home:
3 Beds, 2 Baths, 1250 Sq. ft, Sleeps 6
Location:
Windsor Hills, Florida
Features:
Air Conditioning, Swimming Pool, Hot Tub, Wifi, Satellite/Cable, Family/Kid Friendly, Games Room, No Smoking, Parks Nearby, Golf Course Nearby

Rate Info.

from $65 per night
Details
Sleeps 6

$110 per night

3 Miles to Disney No Extra Fee Gated & Secure Free WiFi

3 Beds3 Baths1800 Sq. ft

Condo

( Owner Manager )

Home:
3 Beds, 3 Baths, 1800 Sq. ft, Sleeps 6
Location:
Windsor Palms, Florida
Features:
Air Conditioning, Swimming Pool, Hot Tub, Wifi, Satellite/Cable, Family/Kid Friendly, Games Room, No Smoking, Parks Nearby, Beach Nearby, Golf Course Nearby

Rate Info.

from $110 per night
Details
Sleeps 8

$128 per night

Mickey's Ritz @ Veranda Palms

4 Beds3 Baths2356 Sq. ft

Family Villa

( Owner Manager )

Home:
4 Beds, 3 Baths, 2356 Sq. ft, Sleeps 8
Location:
Veranda Palms, Florida
Features:
Air Conditioning, Swimming Pool, Hot Tub, Wifi, Satellite/Cable, Family/Kid Friendly, Games Room, No Smoking, Parks Nearby

Rate Info.

from $128 per night
Details
Sleeps 8

$134 per night

Up-to-date calendar~Quick response~Easy to reserve~Near Disney~Clean~Low cost!

4 Beds3 Baths1970 Sq. ft

Family Home

( Owner Manager )

Home:
4 Beds, 3 Baths, 1970 Sq. ft, Sleeps 8
Location:
Indian Creek Community, Florida
Features:
Air Conditioning, Swimming Pool, Wifi, Satellite/Cable, Family/Kid Friendly, Games Room, No Smoking, Parks Nearby, Golf Course Nearby

Rate Info.

from $134 per night
Details
Sleeps 8

$75 per night

1650 sqft 4BR/3BA condo with lake view,Super close to Disney

4 Beds3 Baths1650 Sq. ft

Apartment

( Owner Manager )

Home:
4 Beds, 3 Baths, 1650 Sq. ft, Sleeps 8
Location:
Sun Lake, Florida
Features:
Air Conditioning, Swimming Pool, Hot Tub, Wifi, Satellite/Cable, Family/Kid Friendly, Games Room, No Smoking, Parks Nearby, Golf Course Nearby

Rate Info.

from $75 per night
Details
Sleeps 8

$125 per night

Close to Disney Sleeps 8

4 Beds3 Baths2384 Sq. ft

Family Home

( Management Company )

Home:
4 Beds, 3 Baths, 2384 Sq. ft, Sleeps 8
Location:
Crescent Lakes, Florida
Features:
Air Conditioning, Swimming Pool, Wifi, Satellite/Cable, Family/Kid Friendly, No Smoking, Parks Nearby

Rate Info.

from $125 per night
Details
Sleeps 8

$135 per night

4 Bedrooms / 3 Bathrooms on Sunset lakes in Kissimmee

4 Beds3 Baths1701 Sq. ft

Family Home

( Management Company )

Home:
4 Beds, 3 Baths, 1701 Sq. ft, Sleeps 8
Location:
Sunset Lakes, Florida
Features:
Air Conditioning, Swimming Pool, Wifi, Satellite/Cable, Family/Kid Friendly, No Smoking, Parks Nearby

Rate Info.

from $135 per night
Details
Sleeps 8

$125 per night

Floridian Comfort with Space to Relax

4 Beds2 Baths1601 Sq. ft

Apartment

( Management Company )

Home:
4 Beds, 2 Baths, 1601 Sq. ft, Sleeps 8
Location:
Indian Ridge Oaks, Florida
Features:
Air Conditioning, Swimming Pool, Wifi, Satellite/Cable, Family/Kid Friendly, Games Room, No Smoking, Parks Nearby, Golf Course Nearby

Rate Info.

from $125 per night
Details
Sleeps 8

$125 per night

4 Bed Luxury and Close to Disney

4 Beds3 Baths1834 Sq. ft

Family Home

( Management Company )

Home:
4 Beds, 3 Baths, 1834 Sq. ft, Sleeps 8
Location:
Windsor Palms Resort, Florida
Features:
Air Conditioning, Swimming Pool, Hot Tub, Wifi, Satellite/Cable, Family/Kid Friendly, No Smoking, Parks Nearby, Golf Course Nearby

Rate Info.

from $125 per night
Details
Sleeps 8

$75 per night

2 Miles to Disney,1808 sqft 4BR/3BA Townhome GREAT LOCATION

4 Beds2 Baths1808 Sq. ft

Family Villa

( Owner Manager )

Home:
4 Beds, 2 Baths, 1808 Sq. ft, Sleeps 8
Location:
Oakwater Resort, Florida
Features:
Air Conditioning, Swimming Pool, Hot Tub, Wifi, Satellite/Cable, Family/Kid Friendly, Games Room, No Smoking, Parks Nearby, Golf Course Nearby

Rate Info.

from $75 per night
Details
Sleeps 9

$200 per night

Gardenia Villa

4 Beds3 Baths2360 Sq. ft

Family Villa

( Owner Manager )

Home:
4 Beds, 3 Baths, 2360 Sq. ft, Sleeps 9
Location:
Formosa Gardens Estates, Florida
Features:
Air Conditioning, Swimming Pool, Wifi, Satellite/Cable, Family/Kid Friendly, No Smoking

Rate Info.

from $200 per night
Details
Sleeps 8

$175 per night

Florida Luxury and Just a Stone's Throw from Disney

4 Beds3 Baths2449 Sq. ft

Family Home

( Management Company )

Home:
4 Beds, 3 Baths, 2449 Sq. ft, Sleeps 8
Location:
Formosa Gardens, Florida
Features:
Air Conditioning, Swimming Pool, Wifi, Satellite/Cable, Family/Kid Friendly, Games Room, No Smoking

Rate Info.

from $175 per night
Details
Sleeps 8

$75 per night

4br/3ba TownHome With Hot Tub/lake View,Near Disney,Seaworld,Convention Center

4 Beds3 Baths1500 Sq. ft

Family Villa

( Owner Manager )

Home:
4 Beds, 3 Baths, 1500 Sq. ft, Sleeps 8
Location:
Kissimmee, Florida
Features:
Air Conditioning, Swimming Pool, Hot Tub, Wifi, Satellite/Cable, Family/Kid Friendly, Games Room, No Smoking, Parks Nearby, Golf Course Nearby

Rate Info.

from $75 per night
Details
Sleeps 10

$75 per night

4br/3ba TownHome/Hot Tub,Near Disney,Seaworld

4 Beds3 Baths1512 Sq. ft

Family Villa

( Owner Manager )

Home:
4 Beds, 3 Baths, 1512 Sq. ft, Sleeps 10
Location:
Coral Cay Resort, Florida
Features:
Air Conditioning, Swimming Pool, Hot Tub, Wifi, Satellite/Cable, Family/Kid Friendly, No Smoking, Parks Nearby, Golf Course Nearby

Rate Info.

from $75 per night
Details