1+ Vacation Rentals Near Windsor Hills |
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Irish Ridge Cabins - Vacation Rentals in Windsor Hills

The Cozy Cabin From US $344
         

New
House
The Cozy Cabin
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  • Balcony/Terrace

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Luxury Places to Stay in Windsor Hills

Over 2272+ Luxury Places to Stay in or Near Windsor Hills
Last Minute Disney! Private Pool, Hot Tub, Game Room & Themed Bedrooms. Book Now! #56591 From US $3,145
         

New
Villa
Last Minute Disney! Private Pool, Hot Tub, Game Room & Themed Bedrooms. Book Now! #56591
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6BR Greenview Pool Getaway Only 2 miles to Disney From US $2,285
         

New
House
6BR Greenview Pool Getaway Only 2 miles to Disney
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  • Pool

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Last Minute Disney! Private Pool, Hot Tub, Game Room & Themed Bedrooms. Book Now! #56517 From US $2,226
         

2.0 (1 Review)
Villa
Last Minute Disney! Private Pool, Hot Tub, Game Room & Themed Bedrooms. Book Now! #56517
  • Air Conditioner
  • Parking
  • Pool

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Windsor Hills 5br Private Pool, Near Disney From US $2,190
         

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New
House
Windsor Hills 5br Private Pool, Near Disney
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Immersive Themed Villa in Resort 4mi to Disney with Game Room and Private Pool From US $1,803
         

New
Villa
Immersive Themed Villa in Resort 4mi to Disney with Game Room and Private Pool
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  • Pet Friendly

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Cozy 6br Home w/Private Pool Spa in Windsor Hills From US $1,658
         

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4.0 (1 Review)
House
Cozy 6br Home w/Private Pool Spa in Windsor Hills
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  • Parking
  • Pool

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CW7650-204 Windsor Hills Resort Vacation Condo From US $1,144
         

New
House
CW7650-204 Windsor Hills Resort Vacation Condo
  • Air Conditioner
  • Accessibility
  • Security/Safety

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Huge 6BR Home in Windsor Hills Resort From US $1,144
         

New
House
Huge 6BR Home in Windsor Hills Resort
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating

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Top-Rated Vacation Rentals with a Pool in Windsor Hills

Over 1961+ Top-Rated Vacation Rentals with a Pool in or Near Windsor Hills
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear From US $564
         

10.0 (364 Reviews)
House
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
  • Air Conditioner
  • Parking
  • Pet Friendly

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Windsor Poolside Escape with Stunning Pool View-Perfect for Families! From US $259
         

10.0 (307 Reviews)
Condo
Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
  • Air Conditioner
  • Parking
  • Pool

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Our DisneyDreamVilla - minutes to DisneyWorld! From US $330
         

10.0 (251 Reviews)
Villa
Our DisneyDreamVilla - minutes to DisneyWorld!
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  • Pool

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Mickeys Magical Villa Disney Five Star Pool Villa Home at Windsor Hills From US $253
         

10.0 (226 Reviews)
Villa
Mickeys Magical Villa Disney Five Star Pool Villa Home at Windsor Hills
  • Air Conditioner
  • Parking
  • Pool

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Steps from Waterpark/Pool. Next to Disney w/Frozen, Aladdin, Beauty&Beast theme From US $251
         

10.0 (226 Reviews)
Condo
Steps from Waterpark/Pool. Next to Disney w/Frozen, Aladdin, Beauty&Beast theme
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  • Pool

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Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills From US $345
         

10.0 (224 Reviews)
House
Villa Sonrisa - 5 Bedroom/5 Bath Luxury, Minutes To Disney In Windsor Hills
  • Air Conditioner
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  • Pool

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Luxury for You, Fun for the Kids! 3BR/3BA 2 Miles from Disney From US $252
         

10.0 (207 Reviews)
House
Luxury for You, Fun for the Kids! 3BR/3BA 2 Miles from Disney
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Wonderful Vacation Villa/Close to Disney, Epcot, Wide World of Sports and Golf From US $308
         

10.0 (194 Reviews)
House
Wonderful Vacation Villa/Close to Disney, Epcot, Wide World of Sports and Golf
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  • Parking
  • Pool

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Pet-Friendly Vacation Rentals in Windsor Hills

Over 100+ Pet-Friendly Vacation Rentals in or Near Windsor Hills
Hot Tub. Little Mermaid and Harry Potter Theme. Closest To Disney Private Pool From US $348
         

9.6 (128 Reviews)
Villa
Hot Tub. Little Mermaid and Harry Potter Theme. Closest To Disney Private Pool
  • Air Conditioner
  • Parking
  • Pet Friendly

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Michael's Windsor Hills Castle From US $661
         

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New
House
Michael's Windsor Hills Castle
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T7676F/Windsor Hills Resort/3Bed/POOL/Pet Friendly From US $139
         

10.0 (21 Reviews)
House
T7676F/Windsor Hills Resort/3Bed/POOL/Pet Friendly
  • Air Conditioner
  • Pet Friendly
  • TV

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Livin the Dream❤️Closest FREE Resort to Disney! 3 Kings From US $451
         

10.0 (101 Reviews)
House
Livin the Dream❤️Closest FREE Resort to Disney! 3 Kings
  • Air Conditioner
  • Parking
  • Pet Friendly

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❤️FREE Resort, 3 Kings, 4 Parking Spaces, AC Game Rm From US $607
         

10.0 (88 Reviews)
House
❤️FREE Resort, 3 Kings, 4 Parking Spaces, AC Game Rm
  • Air Conditioner
  • Parking
  • Pet Friendly

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South facing pool with no rear neighbors! Free bbq grill and pool & spa heat. From US $299
         

10.0 (65 Reviews)
House
South facing pool with no rear neighbors! Free bbq grill and pool & spa heat.
  • Air Conditioner
  • Parking
  • Pet Friendly

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*NEW*Theater, FREE Resort, 3 Kings, 2 mi WDW From US $626
         

10.0 (59 Reviews)
House
*NEW*Theater, FREE Resort, 3 Kings, 2 mi WDW
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  • Pet Friendly

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❤️Poolside TV, 3 Kings, FREE Waterpark, AC Game Rm From US $451
         

10.0 (48 Reviews)
House
❤️Poolside TV, 3 Kings, FREE Waterpark, AC Game Rm
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Windsor Hills

Over 1080+ Large Vacation Homes & Villas in or Near Windsor Hills
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills From US $397
         

10.0 (190 Reviews)
Villa
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
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Dream Villa From US $231
         

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8.7 (3 Reviews)
House
Dream Villa
  • Air Conditioner
  • Parking
  • Pool

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Windsor Hills by Nova From US $468
         

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6.0 (2 Reviews)
House
Windsor Hills by Nova
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Luxury 5 Stars Home w/Princess & Mickey Themed Rooms, Game Room Private Pool/Spa From US $357
         

10.0 (106 Reviews)
House
Luxury 5 Stars Home w/Princess & Mickey Themed Rooms, Game Room Private Pool/Spa
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  • Parking
  • Pool

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Luxury 5 Star Vacation Villa - Frozen Themed Room From US $252
         

9.8 (90 Reviews)
Villa
Luxury 5 Star Vacation Villa - Frozen Themed Room
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Three miles to Disneys From US $381
         

9.8 (125 Reviews)
Villa
Three miles to Disneys
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  • Parking
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Magical Family Escape in 6 BDRM Home with South Facing Pool close to Disney From US $533
         

9.8 (86 Reviews)
House
Magical Family Escape in 6 BDRM Home with South Facing Pool close to Disney
  • Air Conditioner
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  • Pool

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Luxury 5 Star Vacation Villa- Free WiFi & Long Distance From US $344
         

10.0 (62 Reviews)
Villa
Luxury 5 Star Vacation Villa- Free WiFi & Long Distance
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  • Pool

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Wheelchair Accessible Vacation Homes in Windsor Hills

Over 332+ Wheelchair Accessible Vacation Homes in or Near Windsor Hills
Fantastic Pool & Free Water Park only Minutes to Walt Disney Worlds Front Gate! From US $214
         

9.8 (216 Reviews)
Condo
Fantastic Pool & Free Water Park only Minutes to Walt Disney Worlds Front Gate!
  • Air Conditioner
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Windsor Hills Resort Kissimmee - Disney Area From US $94
         

6.0 (19 Reviews)
Apartment
Windsor Hills Resort Kissimmee - Disney Area
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Mickey s Hideaway Windsor Hills Resort From US $428
         

New
Apartment
Mickey s Hideaway Windsor Hills Resort
  • Pool
  • Wheelchair Accessible
  • Balcony/Terrace

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Palm Tree Paradise! Bright Tropical Fun with “Frozen” Bedroom - 3 mi from WDW From US $192
         

9.8 (24 Reviews)
Condo
Palm Tree Paradise! Bright Tropical Fun with “Frozen” Bedroom - 3 mi from WDW
  • Air Conditioner
  • Parking
  • Pool

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New Water Park! Huge Pool, 5 Minutes to Disney World!🏝 From US $189
         

9.8 (275 Reviews)
Condo
New Water Park! Huge Pool, 5 Minutes to Disney World!🏝
  • Air Conditioner
  • Parking
  • Pool

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Luxurious Mickey Themed Condo - Kids Will Love It! Only 2 Miles to Disney! From US $157
         

9.8 (124 Reviews)
Condo
Luxurious Mickey Themed Condo - Kids Will Love It! Only 2 Miles to Disney!
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WOW! All NEW! Fully Renovated Kitchen and Bathrooms, Luxuriously Finished 405 From US $164
         

9.4 (40 Reviews)
Condo
WOW! All NEW! Fully Renovated Kitchen and Bathrooms, Luxuriously Finished 405
  • Air Conditioner
  • Parking
  • Pool

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Vacation Rental near Disney, Univeral Studios, Epic, w/free parking and Wi-Fi. From US $156
         

9.2 (220 Reviews)
Condo
Vacation Rental near Disney, Univeral Studios, Epic, w/free parking and Wi-Fi.
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Windsor Hills Varoom and Airbnb Places to Stay Under $200

Over 425+ Windsor Hills Varoom and Airbnb Places to Stay Under $200
WINNER:TOP VACATION RENTAL , CERTIFICATE OF EXCELLENCE From US $169
         

10.0 (112 Reviews)
House
WINNER:TOP VACATION RENTAL , CERTIFICATE OF EXCELLENCE
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Windsor Hills Resort Poolside Ground Floor 3 Bed Condo From US $200
         

10.0 (4 Reviews)
Apartment
Windsor Hills Resort Poolside Ground Floor 3 Bed Condo
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Beautiful Condo - close to Disney portal ! 205 From US $190
         

New
Apartment
Beautiful Condo - close to Disney portal ! 205
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Windsor Hills Townhome | Across from Clubhouse | Mickey-Themed Room | Sleeps 6 From US $181
         

9.8 (69 Reviews)
House
Windsor Hills Townhome | Across from Clubhouse | Mickey-Themed Room | Sleeps 6
  • Air Conditioner
  • Pool
  • TV

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Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8 From US $178
         

8.8 (88 Reviews)
Condo
Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8
  • Air Conditioner
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Modern condo in resort, 5 min to Disney. WiFi, water slides, pool, arcade! From US $190
         

9.6 (90 Reviews)
Condo
Modern condo in resort, 5 min to Disney. WiFi, water slides, pool, arcade!
  • Air Conditioner
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Windsor Hills - Right at Disney's Doorstep. Universal Studios, SeaWorld. From US $180
         

9.0 (54 Reviews)
Condo
Windsor Hills - Right at Disney's Doorstep. Universal Studios, SeaWorld.
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Comrow Hideout | Second Floor Condo with Kids Bedroom and Upgraded Kitchen From US $158
         

7.8 (13 Reviews)
Condo
Comrow Hideout | Second Floor Condo with Kids Bedroom and Upgraded Kitchen
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Instantly Bookable Vacation Homes in Windsor Hills

Over 1530+ Instantly Bookable Vacation Homes in or Near Windsor Hills
Luxury 5 Star Vacation Villa - Frozen Themed Room From US $336
         

9.8 (70 Reviews)
Villa
Luxury 5 Star Vacation Villa - Frozen Themed Room
  • Air Conditioner
  • Parking
  • Pool

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Free Water Park! 4BR/4BA, Private Pool & Game Room- Windsor Hills (7739TB) From US $572
         

8.0 (49 Reviews)
House
Free Water Park! 4BR/4BA, Private Pool & Game Room- Windsor Hills (7739TB)
  • Air Conditioner
  • Pool
  • Private Pool

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Windsor Hills Resort 5 Bedroom Private Pool+Spa Home From US $517
         

9.2 (27 Reviews)
House
Windsor Hills Resort 5 Bedroom Private Pool+Spa Home
  • Air Conditioner
  • Parking
  • Pool

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🏰 Magical 6-Bed Family Villa ✨[FREE Heated Pool, Spa & BBQ] 5 Mins to Disney 🎢 From US $325
         

9.8 (185 Reviews)
House
🏰 Magical 6-Bed Family Villa ✨[FREE Heated Pool, Spa & BBQ] 5 Mins to Disney 🎢
  • Air Conditioner
  • Parking
  • Pool

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Magical 5 bedroom villa, extended pool deck and movie theatre room near Disney From US $434
         

9.6 (116 Reviews)
House
Magical 5 bedroom villa, extended pool deck and movie theatre room near Disney
  • Air Conditioner
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5/5 Pool home with AC game room & themed rooms in Windsor Hills-5 mins to Disney From US $363
         

9.6 (110 Reviews)
House
5/5 Pool home with AC game room & themed rooms in Windsor Hills-5 mins to Disney
  • Air Conditioner
  • Parking
  • Pool

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Tinkerbell's Hideaway From US $273
         

9.6 (94 Reviews)
Condo
Tinkerbell's Hideaway
  • Air Conditioner
  • Parking
  • Pool

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YOLO HOUSE - WINDSOR HILLS : LUXURY TIKI BAR & BBQ : ALL DAY SUN :NEAR DISNEY From US $504
         

9.4 (126 Reviews)
Villa
YOLO HOUSE - WINDSOR HILLS : LUXURY TIKI BAR & BBQ : ALL DAY SUN :NEAR DISNEY
  • Air Conditioner
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About Windsor Hills Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Irishridgecabins Windsor Hills, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windsor Hills. Places to stay near Windsor Hills with prices averaging $344 a night.

Irishridgecabins makes it easy and safe to find and compare vacation rentals in Windsor Hills with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Windsor Hills

Type Count
Vacation Homes 1

Use these Quick Filters to Find a Vacation Rental in Windsor Hills

★ Pro Tip: Irishridgecabins makes it easy to compare the best listings on Irishridgecabins homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Irishridgecabins homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windsor Hills.

Weather in Windsor Hills

View the weather forecast for Windsor Hills before booking your Windsor Hills Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Complexes around Windsor Hills, FL


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