Windsor Hills Vacation Rentals, Windsor Hills Condos, Houses, Townhomes & Villas

Branch out from your usual travel routine and consider staying in one of several Windsor Hills vacation rentals when planning your next Windsor Hills vacation in Florida. Whether you’re looking for a relaxing golf vacation in Windsor Hills or a Disney vacation for the family, you’ll stretch your precious dollar farther in a Windsor Hills rental than you would at a high-priced Disney resort.

Vacation homes in Windsor Hills range from quaint Windsor Hills condos to elegant Windsor Hills villas and can accommodate any sized group. Looking to splurge? Choose a Windsor Hills luxury rental with its own swimming pool and hot tub – perfect after a long day of exploring Disneyworld. Or unwind on one of the golf courses in Windsor Hills; there are many in the Kissimmee area and some are considered the best in the world.

Of course there are several Windsor Hills rentals to fit those strapped for cash, and the best part is Windsor Hills rental homes have their own kitchens so you don’t have to spend money at Windsor Hills tourist traps for every meal! Pack a lunch to bring to the park and save even more money. Windsor Hills vacation rentals offer more bang for your buck, so start planning your Windsor Hills, FL vacation today!

Expand your search for Florida vacation rentals to include Miami vacation rentals and Ft. Lauderdale rentals in South Florida, Destin vacation rentals and Siesta Key rentals on the Gulf Coast, or Orlando vacation home rentals near Disney.


Windsor Hills Vacation Rentals

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Windsor Hills townhome rental - heated lagoon style pool
3 Bedrooms, Sleeps 8
  • Townhome
  • 3 Bathrooms
  • resort
  • accept credit card
Rates per property (USD)
$85 - $119/night
$595 - $833/week
Windsor Hills condo rental - Lagoon Style Pool
2 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • resort
  • accept credit card
Rates per property (USD)
$85 - $125/night
Windsor Hills condo rental
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • resort
  • accept credit card
Rates per property (USD)
$75/night
Windsor Hills townhome rental - Luxurious Master Bedroom
3 Bedrooms, Sleeps 6
  • Townhome
  • 3 Bathrooms
  • resort, rural
  • accept credit card
Rates per property (USD)
$99 - $149/night
$650 - $900/week
Windsor Hills condo rental - Spacious Family Room. 42 in LCD TV/DVD/CD
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • resort
  • accept credit card
Rates per property (USD)
$105 - $145/night
$735 - $1,015/week
Windsor Hills condo rental - Beautiful Resort Pool
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • lake
  • accept credit card
Rates per property (USD)
$693 - $1,020/week
Windsor Hills house rental - Living Room Opening to Large Lanai/ Pool/ Spa
5 Bedrooms, Sleeps 10
  • House
  • 5 Bathrooms
  • lake, resort
  • accept credit card
Rates per property (USD)
$190 - $290/night
$1,330 - $2,030/week
Windsor Hills villa rental - Magical Disney Villa
6 Bedrooms, Sleeps 14
  • Villa
  • 4 Bathrooms
  • resort
  • air-conditioning
Rates per property (USD)
$199 - $315/night
$1,390 - $2,205/week
Windsor Hills house rental - Our beautiful villa
6 Bedrooms, Sleeps 12
  • House
  • 4 Bathrooms
  • swimming pool
  • air-conditioning
Windsor Hills house rental - GAMES ROOM
4 Bedrooms, Sleeps 10
  • House
  • 4 Bathrooms
  • town
  • swimming pool
Windsor Hills townhome rental - Open Floorplan with Pool Right Outside!
3 Bedrooms, Sleeps 6
  • Townhome
  • 3 Bathrooms
  • resort
  • accept credit card
Windsor Hills townhome rental - Our Townhome
3 Bedrooms, Sleeps 8
  • Townhome
  • 3 Bathrooms
  • resort
  • accept credit card
Windsor Hills condo rental - Dining & Living Room
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • resort
  • accept credit card
Rates per property (USD)
$90 - $135/night
$630 - $945/week
Windsor Hills house rental - Front view
5 Bedrooms, Sleeps 12
  • House
  • 5 Bathrooms
  • resort, town
  • accept credit card
Rates per property (USD)
$1,599 - $1,999/week
Windsor Hills house rental - Front of the house
6 Bedrooms, Sleeps 16
  • House
  • 4 Bathrooms
  • resort
  • swimming pool
Windsor Hills villa rental - Lounge
6 Bedrooms, Sleeps 14
  • Villa
  • 4 Bathrooms
  • resort
  • accept credit card
Windsor Hills townhome rental - Our unit
3 Bedrooms, Sleeps 6
  • Townhome
  • 3 Bathrooms
  • swimming pool
  • air-conditioning
SPECIAL OFFER! Save 10% + FREE Pool heating (December 21 - August 29)
Windsor Hills townhome rental - Private Pool (heating optional)
3 Bedrooms, Sleeps 8
  • Townhome
  • 3 Bathrooms
  • resort
  • accept credit card
Rates per property (USD)
$99 - $165/night
Special Offer
Windsor Hills condo rental - Living and Dining Area
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • resort
  • accept credit card
SPECIAL OFFER! Spectacular Last Minute Deals!!! Dec-Feb (December 1 - February 28)
Windsor Hills villa rental - Private south-facing pool on over-sized corner lot
4 Bedrooms, Sleeps 11
  • Villa
  • 4 Bathrooms
  • resort
  • swimming pool
Rates per property (USD)
$140 - $225/night
$980 - $1,575/week
Special Offer
Windsor Hills townhome rental - Relax and unwind in this tropical retreat!
3 Bedrooms, Sleeps 7
  • Townhome
  • 3 Bathrooms
  • resort
  • accept credit card
Rates per property (USD)
$105 - $118/night
$735/week
Windsor Hills villa rental - Front of House
6 Bedrooms, Sleeps 14
  • Villa
  • 4 Bathrooms
  • resort, town
  • accept credit card
Rates per property (USD)
$147 - $325/night
$1,024 - $2,275/week
Windsor Hills townhome rental - Great Room
3 Bedrooms, Sleeps 8
  • Townhome
  • 3 Bathrooms
  • resort
  • accept credit card
Rates per property (USD)
$105 - $130/night
Windsor Hills condo rental - Living Room
3 Bedrooms, Sleeps 8
  • Condo
Rates per property (USD)
$85/night
$595/week
Windsor Hills condo rental - Living Room
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • resort
  • accept credit card
Rates per property (USD)
$79 - $139/night
$553 - $973/week
Windsor Hills house rental - Brand New Executive Home!  3 Miles from Disney
6 Bedrooms, Sleeps 14
  • House
  • 4 Bathrooms
  • resort
  • accept credit card
SPECIAL OFFER! Save 10% + FREE pool heating (December 15 - June 27)
Windsor Hills villa rental - Pool View
5 Bedrooms, Sleeps 12
  • Villa
  • 5 Bathrooms
  • resort
  • accept credit card
Rates per property (USD)
$180 - $280/night
Special Offer
SPECIAL OFFER! 5-Star Luxury starting at $195 per night (November 1 - December 31)
Windsor Hills house rental - Spacious Formal Living Room
6 Bedrooms, Sleeps 14
  • House
  • 4 Bathrooms
  • near the ocean, resort
  • accept credit card
Rates per property (USD)
$195 - $340/night
$1,365 - $2,380/week
Special Offer
SPECIAL OFFER! JANUARY SPECIAL $200 + FREE POOL HEAT (November 9 - February 28)
Windsor Hills villa rental - Disney themed Bedroom at www.mickeyatwindsorhills
6 Bedrooms, Sleeps 13
  • Villa
  • 4 Bathrooms
  • resort
  • accept credit card
Special Offer
SPECIAL OFFER! $10 Off Per Night!! (November 5 - December 5)
Windsor Hills condo rental - Lounge
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • lake, resort
  • accept credit card
Rates per property (USD)
$100/night
$700/week
Special Offer