Oceanfront Rentals in Windsor Hills, FL: Compare 10+ Sites & Save

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1759 Best Oceanfront Rentals in Windsor Hills (Starting from $152)

Olivia's Dream Villa on WindsorHills
Olivia's Dream Villa on WindsorHills
Villa
Orlando, FL, USA
0.0k from Windsor Hills center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

5 Bedrooms10 Guests
9.1

Superb

33 reviews

$278
Average price / night
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Amazing Lakeview Windsor Hills resort, 6BR, 2 massage chairs
Amazing Lakeview Windsor Hills resort, 6BR, 2 massage chairs
Villa
Kissimmee, FL, 34747, United States
0.1k from Windsor Hills center

AC, Arcade, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

6 Bedrooms14 Guests
10.0

Exceptional

58 reviews

$664
Average price / night
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The Pink House at Windsor Hills
The Pink House at Windsor Hills
House
Orlando, FL, USA
0.1k from Windsor Hills center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings

6 Bedrooms12 Guests
9.2

Superb

9 reviews

$275
Average price / night
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Lakefront Windsor Hills - 6 Bed 4 Bath Home with Custom Mickey Mouse Heated Pool
Lakefront Windsor Hills - 6 Bed 4 Bath Home with Custom Mickey Mouse Heated Pool
House
Kissimmee, FL, 34747, United States
0.1k from Windsor Hills center

AC, Arcade, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

6 Bedrooms12 Guests
10.0

Exceptional

29 reviews

$422
Average price / night
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South Facing Dream Pool Home
South Facing Dream Pool Home
House
Orlando, FL, USA
0.1k from Windsor Hills center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay

5 Bedrooms12 Guests
1.0

Review score

1 reviews

$594
Average price / night
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Massive Windsor Hills Private Pool Home! 2638 Daulby- Don't Miss This!
Massive Windsor Hills Private Pool Home! 2638 Daulby- Don't Miss This!
House
Kissimmee, FL, 34747, United States
0.1k from Windsor Hills center

AC, Arcade, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen

6 Bedrooms14 Guests
9.6

Exceptional

19 reviews

$217
Average price / night
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Windsor Hills Resort - Enchanted Crystal Castle
Windsor Hills Resort - Enchanted Crystal Castle
House
Orlando, FL, USA
0.1k from Windsor Hills center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

5 Bedrooms12 Guests
New to Booking
$284
Average price / night
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Free Arcade! All Themed! South Facing Pool & Spa!
Free Arcade! All Themed! South Facing Pool & Spa!
Villa
Kissimmee, FL, 34747, United States
0.2k from Windsor Hills center

AC, Arcade, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

5 Bedrooms10 Guests
New to Booking
$488
Average price / night
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Spacious 6BR Villa Pool Parking Near Disney World
Spacious 6BR Villa Pool Parking Near Disney World
Villa
Orlando, FL, USA
0.1k from Windsor Hills center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Onsen, Lodgings, Vacation rentals

6 Bedrooms14 Guests
5.1

Review score

13 reviews

$331
Average price / night
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Stay in this wonderful home just 3 miles from Disney World!
Stay in this wonderful home just 3 miles from Disney World!
House
Kissimmee, FL, 34747, United States
0.2k from Windsor Hills center

AC, Arcade, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

6 Bedrooms12 Guests
9.8

Exceptional

13 reviews

$463
Average price / night
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WH2618DS Windsor Hills Retreat
WH2618DS Windsor Hills Retreat
House
Orlando, FL, USA
0.1k from Windsor Hills center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

4 Bedrooms9 Guests
New to Booking
$214
Average price / night
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Orlando Villa 6472 - Family Getaway Home
Orlando Villa 6472 - Family Getaway Home
House
Orlando, FL, 34747, United States
0.3k from Windsor Hills center

AC, Arcade, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

6 Bedrooms17 Guests
New to Booking
$531
Average price / night
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Windsor Dream - 6 bedroom resort pool home
Windsor Dream - 6 bedroom resort pool home
House
Orlando, FL, USA
0.1k from Windsor Hills center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

6 Bedrooms12 Guests
7.7

Good

8 reviews

$356
Average price / night
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6/4 Home Pool/Spa Close to Disney,  Free Water Park Use, Game RMThemed, WIFI BBQ
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
House
Kissimmee, FL, 34747, United States
0.3k from Windsor Hills center

AC, Arcade, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Hot Tub

6 Bedrooms14 Guests
9.4

Superb

258 reviews

$316
Average price / night
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Home with Lakeview Close to Disney w Pool
Home with Lakeview Close to Disney w Pool
House
Orlando, FL, USA
0.2k from Windsor Hills center

Parking, Accessibility, Hot Tub, Spa, Sports/Activities, View, Wellness Facilities

6 Bedrooms14 Guests
4.0

Review score

1 reviews

$382
Average price / night
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Awesome!! 6BR 4BA Luxury , Games-room, DUAL Waterslides, Spa
Awesome!! 6BR 4BA Luxury , Games-room, DUAL Waterslides, Spa
House
Four Corners, FL, 34747, United States
0.3k from Windsor Hills center

AC, Arcade, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

6 Bedrooms12 Guests
9.8

Exceptional

176 reviews

$351
Average price / night
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Immersive Themed Villa in Resort 4mi to Disney with Game Room and Private Pool
Immersive Themed Villa in Resort 4mi to Disney with Game Room and Private Pool
Villa
Orlando, FL, USA
0.2k from Windsor Hills center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

6 Bedrooms14 Guests
New to Booking
$1803
Average price / night
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Wonderful Vacation Villa/Close to Disney, Epcot, Wide World of Sports and Golf
Wonderful Vacation Villa/Close to Disney, Epcot, Wide World of Sports and Golf
House
Kissimmee, FL, 34747, United States
0.3k from Windsor Hills center

AC, Arcade, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

5 Bedrooms10 Guests
10.0

Exceptional

199 reviews

$296
Average price / night
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Free Water Park 4BR wPool Game Room 7739TB
Free Water Park 4BR wPool Game Room 7739TB
House
Orlando, FL, USA
0.2k from Windsor Hills center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay

4 Bedrooms10 Guests
7.0

Good

2 reviews

$232
Average price / night
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☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
☆ Location matters! Private palm paradise view from pool - 1 block to waterpark
Villa
Kissimmee, FL, 34747, United States
0.3k from Windsor Hills center

AC, Arcade, Barbecue, Breakfast Available, Crib, Dryer, Fitness Equipment, Free Parking, Heater

5 Bedrooms10 Guests
10.0

Exceptional

24 reviews

$326
Average price / night
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Disney Daze Villa - 5 bed Windsor Hills pool home
Disney Daze Villa - 5 bed Windsor Hills pool home
House
Orlando, FL, USA
0.2k from Windsor Hills center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs

5 Bedrooms10 Guests
9.2

Superb

5 reviews

$224
Average price / night
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Free Arcade! All Rooms Themed! South Facing Pool!
Free Arcade! All Rooms Themed! South Facing Pool!
Villa
Kissimmee, FL, 34747, United States
0.4k from Windsor Hills center

AC, Arcade, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$595
Average price / night
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Windsor Hills 402B No Resort Fees! New Water-Park! Close to Pool and Lakeview
Windsor Hills 402B No Resort Fees! New Water-Park! Close to Pool and Lakeview
Condo
Kissimmee, FL, 34747, United States
0.4k from Windsor Hills center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking

2 Bedrooms6 Guests
9.0

Fabulous

55 reviews

$152
Average price / night
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2 Miles to Disney - 20 sec Walk to Clubhouse - Private Pool - Free Water Park
2 Miles to Disney - 20 sec Walk to Clubhouse - Private Pool - Free Water Park
House
Kissimmee, FL, 34747, United States
0.4k from Windsor Hills center

AC, Arcade, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms8 Guests
9.6

Exceptional

214 reviews

$231
Average price / night
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Updated Windsor Hills Largest Condo - Family Water Park Fun & Near Disney Parks
Updated Windsor Hills Largest Condo - Family Water Park Fun & Near Disney Parks
Condo
Kissimmee, FL, 34747, United States
0.4k from Windsor Hills center

AC, Arcade, Balcony, Dryer, Elevator, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms7 Guests
9.4

Superb

122 reviews

$187
Average price / night
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Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!
Minutes Away from Theme Parks! 3-Bed Townhome, 6 minutes to Disney World!
House
Kissimmee, FL, 34747, United States
0.4k from Windsor Hills center

AC, Arcade, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms6 Guests
10.0

Exceptional

201 reviews

$238
Average price / night
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Vacation in the Sun! Spacious 3 Bedroom, 6 minutes from Disney World!
Vacation in the Sun! Spacious 3 Bedroom, 6 minutes from Disney World!
House
Kissimmee, FL, 34747, United States
0.4k from Windsor Hills center

AC, Arcade, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
10.0

Exceptional

111 reviews

$254
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Oceanfront Rentals in Windsor Hills.

Stay Near Windsor Hills's Top Attractions

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Windsor Hills Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 1759 verified oceanfront rentals in Windsor Hills. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Windsor Hills vary depending on the property size, exact beachfront location, and season. Rates typically start from around $152 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Windsor Hills offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Windsor Hills welcome pets. Currently, 10 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Windsor Hills often include features designed for a comfortable coastal stay, such as Child Friendly, View, and Wellness Facilities. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.