Vacation Rentals

Welcome to Windermere Florida Vacation Rentals

Windermere Travel and Vacation Rental Overview

Windermereis a town in Orange County, Florida, in the United States. As of the 2000 census, the town population was 1,897. According to the U.S. Census Bureau's 2006 estimates, the town had a population of 2,019. It is part of the Orlando–Kissimmee Metropolitan Statistical Area.

Windermere was established in 1889 and works hard to retain a small town feel. For instance, many local streets are dirt roads and street name signs are white concrete posts (see photos). Windermere has been the residence of professional golfer Tiger Woods since 1997 as well as other professional sports figures. However, many celebrities such as Woods actually live in the Isleworth gated community/subdivision which is outside the town limits of Windermere, but utilize the Windermere mailing address.

During late 2007, the Town of Windermere filed a proposal to annex Isleworth and Butler Bay, another wealthy subdivision. This was met with extensive debate from town residents and an objection from Orange County, which stood to lose millions of dollars of property tax revenue. After lengthy discussions, and battles with the county, Isleworth remained in the county, but Butler Bay was annexed into Windermere with over 90% of its residents approving annexation via a mail in ballot. Windermere is also home to famous cyclists, the Windermere Roadies, led by Sir Manny Otero of Winter Garden.
 
       
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Windermere Vacation Rental Homes

Houses 
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Villa
Apartment
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Featured Florida Vacation Rentals 4all in Windermere Property
Paradise Cove Key Largo Oceanfront Mansion
Bed: 4 Bath: 4.5 Sleep: 8, Type: House
Kissimmee, Florida, United States
Paradise Cove of Key Largo offers 6 acres, gated, private, tropical lush landscaping with private marina and boat slip. Oceanfront private estate with ... View Details
6 Bed 3 Bath Private Pool Vacation Rental Home
Bed: 6 Bath: 3 Sleep: 12, Type: House
Kissimmee, Florida, United States
Two Storey Brand New villa fully air conditioned. Only 15 minutes to Disney with South facing private pool, Spa and Games Room. Sleeps up to 12 in 6 B ... View Details
Happys Hideaway - A Home Away From Home in Kissimmee Florida
Bed: 5 Bath: 4 Sleep: 12, Type: House
Kissimmee, Florida, United States
Ever wonder why Happy was always smiling as he whistled while he worked? The Happy life begins at home. Happy’s Hideaway is the perfect “home away fro ... View Details
La Isla at Emerald Island Resort
Bed: 6 Bath: 5 Sleep: 12, Type: House
Kissimmee, Florida, United States
Our beautiful luxury 6 bedroom, 5 bath ranch home is charming on the outside and huge on the inside. It has volume and trey ceilings and beautiful a ... View Details
Beautiful House in Reunion Resort in Orlando
Bed: 3 Bath: 2.5 Sleep: 6, Type: House
Kissimmee, Florida, United States
Welcome to our brand new beautiful 3 bedroom, 2.5 bath vacation house located in the luxurious Reunion Resort & Club in Orlando area, Florida and ... View Details
The Bella Villa
Bed: 5 Bath: 3 Sleep: 10, Type: House
Kissimmee, Florida, United States
A beautiful 5 bedroom 3 bath home with a private, wooded back yard, pool, hot tub and game room! ... View Details
Only 2 Miles to Disney
Bed: 5 Bath: 5 Sleep: 10, Type: House
Kissimmee, Florida, United States
Windsor Hills is a 5 star-rated resort community that is located 2 mi. from Disney Theme Parks. This brand new 5 bedroom (2 Masters) 5 bathrooms vil ... View Details
New Five Bedroom, Five Bath Home in Winsor Hills
Bed: 5 Bath: 5 Sleep: 12, Type: House
Kissimmee, Florida, United States
Beautiful new home 2 miles from Walt Disney World located in the \'Reserve\' section of a 24 hour guard gated resort community. Home has fiv ... View Details
7 bedroom Acadia Estates vacation home just 3 miles from Disney!
Bed: 7 Bath: 6.5 Sleep: 16, Type: House
Kissimmee, Florida, United States
This beautiful 7 bedroom estate home offers amazing amenities to add excitement and comfort to your vacation home experience. The air-conditioned game ... View Details
This Acadia Estates home is just 3 miles from Disney, 3354sq.ft
Bed: 7 Bath: 6.5 Sleep: 16, Type: House
Kissimmee, Florida, United States
This luxurious home is ideal for large families with 3400 square feet of living space! There are 7 bedrooms, with 6 1/2 bathrooms, 5 masters, oversize ... View Details
Fantastic 7 bedroom estate home with game room, only 3 miles from Disney
Bed: 7 Bath: 6.5 Sleep: 16, Type: House
Kissimmee, Florida, United States
The home includes a flat screen computer with broadband Internet and nine TVs overall, including one in each bedroom with either a DVD or VCR player. ... View Details
Magnificent 7 bedroom vacation home only 3 miles from Disney
Bed: 7 Bath: 6.5 Sleep: 16, Type: House
Kissimmee, Florida, United States
You’ll find numerous amenities for you and your guests including a dell flat-screen computer with Internet access, a 52” wide screen TV with DVD and V ... View Details
 
 
 
 
 
 

Windermere Attractions and Activities

Geography

Windermere is located at 28°29´48"N 81°32´2"W / 28.49667°N 81.53389°W / 28.49667; -81.53389 (28.496581, -81.533781). According to the United States Census Bureau, the town has a total area of 2.9 km˛ (1.1 mi˛), all land.

At a Glance

At Keene's Pointe, Castle & Cooke has combined the classical architecture styles of the past with the flowing and open interiors of today. The Keene's Pointe community features 14 unique villages, set among the Butler Chain of Lakes and its golf course.

Over 400 acres just south of Keene's Pointe are designated as the Tibet-Butler Preserve, housing a bird sanctuary and several endangered species of animals and plants.

Windermere is located in Orange County, Florida, just a few miles south-west of Orlando with a population of just over 2,000. Walt Disney World and many other exciting attractions are only a few miles away.

History of Windermere

The area surrounding Keene's Pointe and Windermere is rich in history. For over 100 years, the mild climate and the beauty of the lakes have attracted settlers, farmers, tourists and homeowners.

After the end of the Seminole wars in 1858, the federal government - in an effort to bring settlers & farmers to the area, offered homesteaders 160 acres of free land in exchange for cultivating 5 acres and building a cabin. The resulting development brought more and more settlers, tourists, merchants and farmers to the area, first by dirt trails, then by steamboats and finally by railroads.

The city of Windermere was founded in 1887 and continues to grow as a highly desirable vacation destination and as a community of luxury living. Today's Windermere still shows its past in the historic Town Hall (built 1922-24), Cal Palmer’s original office building (built 1911-12), the well-preserved Bumby house (built 1911) and the Armstrong-Beggs-Parramore house (built 1890 or earlier), which served as the town’s first school in the same year.

Community & Activities

Residents of Windermere enjoy the town hall and surrounding area, which includes the Chase Memorial Library, basketball courts, a municipal office building and the Cal Palmer Memorial Building, named after one of its founding residents. The town hall is listed on the National Register of Historic Places. The town is literally set on a small strip of land amongst the Butler Chain of Lakes, offering residents glorious vistas and a retreat from the sometimes-tropical heat.

Windermere Attractions

Everything changes with time but the little town of Windermere has remained pretty much the same. The Town Council has restricted growth and commercialism and Windermere remains the little Florida citrus town plopped down amid a beautiful chain of lakes.

Universal Studios and Islands of Adventure
Pirate’s Dinner Adventure
Universal Studios VIP Tour
Golden Bear Club

Events & Festivals

  • 3rd Annual Windermere Fall Arts Festival, October 24, 2009
  • Michael Jackson's This Is It, November 17, 2009
  • University of Central Florida Football, Nov 21, 2009
  • Pirate's Dinner Adventure, Nov 30, 2009
  • Latest Windermere Vacation Rental News


    Windermere School Students Visit Ellington Senior Center
    Patch.com
    The “Senior Center Super Stars” are a group of approximately 20 students at Windermere School who are part of the Rachel's Challenge club. There are several clubs throughout the fifth and sixth grade classes, and the students give up one recess a week ...



    Chorley Guardian

    Theatre Review - Lady Windermere's Fan, Royal Exchange, Manchester
    Chorley Guardian
    The Wildean wit tends to be tucked away into the folds of Lady Windermere's Fan, particularly amongst the feast of epigrams that flow through the first act. But it is when the play opens out, to reveal the heartbreak of its story, that a full-blooded ...
    Lysette Anthony as Mrs ErlynneWhatsOnStage.com
    Lady Windermere's Fan, Royal Exchange, ManchesterThe Arts Desk

    all 3 news articles »


    Brathay Windermere Marathon - with slideshow and results
    NW Evening Mail
    Cheered on by some of the Ulverston pub's clientele and wife Trudie, Paul Dewar completed the gruelling Brathay Trust Windermere 10 in 10 Marathon challenge. The sixth annual 262-mile endurance event – 10 marathons over 10 consecutive days – ended on ...
    Shaw reclaims Windermere Marathon women's title as Jefferies wins overallThe Westmorland Gazette

    all 3 news articles »


    Lady Windermere's Fan
    Stage
    It was Oscar Wilde's first major theatrical hit, but Lady Windermere's Fan is rather better known these days for its famous one-liners than its content. And “we are all in the gutter, but some of us are looking at the stars” is an apt description for a ...

    and more »


    7 Stocks Rising on Monster Volume
    TheStreet.com
    By Roberto Pedone 05/23/12 - 01:16 PM EDT WINDERMERE, Fla. (Stockpickr) -- Professional traders running mutual funds and hedge funds don't just look at a stock's price moves; they also track big changes in volume activity. Many times when above average ...

    and more »

     

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    Florida is a diverse state with beautiful beaches, grand resorts, exciting theme parks, island getaways, and sophisticated cities. Inland or coastal, indoors or out, for vacation or forever, the Sunshine State has a time and a place for everyone. The mention of beaches and such riches brings to mind only Florida – the sunshine state – where there is no shortage of exquisite sun-kissed beaches or of charming beachfront and oceanfront vacation homes. The beaches of Florida are not limited to just the coastline of the mainland; there are a large number of barrier islands as well. So, vacationers seeking a beach break in Florida can choose from the beachfront vacation homes on the Atlantic coast, on the coast of the Gulf of Mexico, or on the shores fronting the Intracoastal Waterways.