Estia Villas - Vacation Rentals in Windsor Hills
Villa
10.0
(
205 Reviews
)
6 Bedrooms
4 Bathrooms
12 Guests
2812 ft²
-
Private Pool -
Hot Tub -
Parking -
Pool
US $481
/Night
7 Nights - $3,370
8.7
(
3 Reviews
)
6 Bedrooms
4 Bathrooms
12 Guests
2174.31 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $231
/Night
7 Nights - $1,617
Villa
5 Bedrooms
5 Bathrooms
11 Guests
2342 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $757
/Night
7 Nights - $5,300
Villa
9.6
(
133 Reviews
)
6 Bedrooms
4 Bathrooms
13 Guests
3511 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $369
/Night
7 Nights - $2,580
Villa
9.8
(
126 Reviews
)
7 Bedrooms
4 Bathrooms
14 Guests
3232 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $485
/Night
7 Nights - $3,397
Villa
10.0
(
62 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
1816 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $335
/Night
7 Nights - $2,347
Villa
9.8
(
70 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
1816 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $323
/Night
7 Nights - $2,263
Villa
9.4
(
132 Reviews
)
6 Bedrooms
2 Bathrooms
13 Guests
30268 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $679
/Night
7 Nights - $4,751
See More Windsor Hills Vacation Rentals
Luxury Places to Stay in Windsor Hills
Over 2257+
Luxury Places to Stay in or Near Windsor Hills
5 Bedrooms
5 Bathrooms
12 Guests
2497.23 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $2,190
/Night
7 Nights - $15,330
Villa
6 Bedrooms
4 Bathrooms
14 Guests
2766.32 ft²
-
Oceanfront -
EV Charge Station -
Parking
-
Pool
US $1,803
/Night
7 Nights - $12,621
House
6 Bedrooms
4 Bathrooms
15 Guests
3000 ft²
-
Private Pool
-
Hot Tub
-
Pool
-
Balcony/Terrace
US $1,709
/Night
7 Nights - $11,961
Villa
10.0
(
37 Reviews
)
5 Bedrooms
5 Bathrooms
12 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,384
/Night
7 Nights - $9,685
Villa
4.0
(
1 Review
)
6 Bedrooms
4 Bathrooms
12 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $1,301
/Night
7 Nights - $9,110
House
5 Bedrooms
5 Bathrooms
11 Guests
-
Parking
-
Internet -
Child Friendly -
Security/Safety
US $999
/Night
7 Nights - $6,993
6 Bedrooms
4 Bathrooms
12 Guests
2809.38 ft²
-
Parking
-
Air Conditioner -
Child Friendly
-
Wheelchair Accessible
US $940
/Night
7 Nights - $6,580
Find More Windsor Hills Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Windsor Hills
Over 1967+
Top-Rated Vacation Rentals with a Pool in or Near Windsor Hills
House
10.0
(
382 Reviews
)
6 Bedrooms
4 Bathrooms
14 Guests
3534 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $581
/Night
7 Nights - $4,070
Condo
10.0
(
319 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $282
/Night
7 Nights - $1,971
Condo
10.0
(
236 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1245 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $355
/Night
7 Nights - $2,484
Villa
10.0
(
226 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
2000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $366
/Night
7 Nights - $2,562
House
10.0
(
207 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
1496 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $202
/Night
7 Nights - $1,414
House
10.0
(
198 Reviews
)
5 Bedrooms
5 Bathrooms
12 Guests
2800 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $405
/Night
7 Nights - $2,835
Villa
10.0
(
172 Reviews
)
5 Bedrooms
5 Bathrooms
12 Guests
2800 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $455
/Night
7 Nights - $3,185
House
10.0
(
172 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
2000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $381
/Night
7 Nights - $2,664
Pet-Friendly Vacation Rentals in Windsor Hills
Over 101+
Pet-Friendly Vacation Rentals in or Near Windsor Hills
House
10.0
(
111 Reviews
)
6 Bedrooms
4 Bathrooms
16 Guests
3500 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $676
/Night
7 Nights - $4,734
6 Bedrooms
4 Bathrooms
12 Guests
2809.38 ft²
-
Parking
-
Pool
-
Air Conditioner
-
Internet
US $661
/Night
7 Nights - $4,627
House
10.0
(
21 Reviews
)
1 Bedroom
1 Bathroom
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Pet Friendly
US $139
/Night
7 Nights - $975
House
10.0
(
96 Reviews
)
6 Bedrooms
4 Bathrooms
16 Guests
3500 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $635
/Night
7 Nights - $4,445
House
10.0
(
66 Reviews
)
6 Bedrooms
4 Bathrooms
15 Guests
3500 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $689
/Night
7 Nights - $4,826
House
10.0
(
64 Reviews
)
6 Bedrooms
5 Bathrooms
15 Guests
2800 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $478
/Night
7 Nights - $3,348
House
10.0
(
58 Reviews
)
6 Bedrooms
4 Bathrooms
16 Guests
3500 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $622
/Night
7 Nights - $4,353
House
10.0
(
42 Reviews
)
3 Bedrooms
3 Bathrooms
8 Guests
1440 ft²
-
Private Pool
-
Parking
-
Pool
-
Kitchen
US $402
/Night
7 Nights - $2,811
See More Pet-Friendly Vacation Rentals in Windsor Hills on PetFriendly.io
Large Vacation Homes & Villas in Windsor Hills
Over 1068+
Large Vacation Homes & Villas in or Near Windsor Hills
House
10.0
(
110 Reviews
)
5 Bedrooms
5 Bathrooms
10 Guests
3000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $451
/Night
7 Nights - $3,160
5 Bedrooms
5 Bathrooms
10 Guests
2378.82 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $244
/Night
7 Nights - $1,708
House
9.0
(
8 Reviews
)
6 Bedrooms
4 Bathrooms
14 Guests
2812 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $723
/Night
7 Nights - $5,060
House
10.0
(
102 Reviews
)
6 Bedrooms
3 Bathrooms
12 Guests
2860 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $641
/Night
7 Nights - $4,488
House
9.4
(
128 Reviews
)
6 Bedrooms
4 Bathrooms
14 Guests
2812 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $396
/Night
7 Nights - $2,772
House
9.2
(
29 Reviews
)
5 Bedrooms
5 Bathrooms
10 Guests
2382 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $365
/Night
7 Nights - $2,552
![🏰 Magical 6-Bed Family Villa ✨[FREE Heated Pool, Spa & BBQ] 5 Mins to Disney 🎢](https://imgservice.123presto.com/640x287/magical-6-bed-family-v-us-kissimmee-ha-121192202-0.jpg)
New
House
9.8
(
194 Reviews
)
6 Bedrooms
4 Bathrooms
13 Guests
2812 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $360
/Night
7 Nights - $2,521
House
9.6
(
120 Reviews
)
5 Bedrooms
5 Bathrooms
12 Guests
2400 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $524
/Night
7 Nights - $3,666
See More Family Vacation Rentals in Windsor Hills on FVR
Wheelchair Accessible Vacation Homes in Windsor Hills
Over 341+
Wheelchair Accessible Vacation Homes in or Near Windsor Hills
Apartment
6.0
(
19 Reviews
)
3 Bedrooms
1 Bathroom
8 Guests
1250.01 ft²
-
Hot Tub
-
Breakfast -
Parking
-
Pool
US $94
/Night
7 Nights - $658
Apartment
1 Bedroom
1 Bathroom
-
Pool
-
Balcony/Terrace
-
Internet
-
Child Friendly
US $435
/Night
7 Nights - $3,048
Condo
9.8
(
218 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1450 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $209
/Night
7 Nights - $1,465
Condo
9.8
(
25 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1400 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $221
/Night
7 Nights - $1,547
Condo
9.8
(
293 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1100 ft²
-
Oceanfront
-
Hot Tub
-
Parking
-
Pool
US $164
/Night
7 Nights - $1,145
Condo
9.8
(
132 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1100 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $169
/Night
7 Nights - $1,181
Condo
9.2
(
232 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1547 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $193
/Night
7 Nights - $1,349
Condo
9.4
(
185 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1250 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $275
/Night
7 Nights - $1,922
Windsor Hills Vacation Rentals and Airbnb Places to Stay Under $200
Over 390+
Windsor Hills Vacation Rentals and Airbnb Places to Stay Under $200
Apartment
10.0
(
4 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1442.36 ft²
-
Oceanfront
-
Parking
-
Pool
-
Ocean View
US $200
/Night
7 Nights - $1,400
Apartment
1 Bedroom
1 Bathroom
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $190
/Night
7 Nights - $1,331
Condo
9.0
(
58 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1450 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $193
/Night
7 Nights - $1,354
Condo
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $194
/Night
7 Nights - $1,356
Condo
9.0
(
20 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1300 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $183
/Night
7 Nights - $1,281
Condo
7.8
(
16 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1300 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $184
/Night
7 Nights - $1,290
Condo
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1400 ft²
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
US $193
/Night
7 Nights - $1,348
Condo
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1399 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $184
/Night
7 Nights - $1,289
See More Windsor Hills Vacation Rental Deals
Instantly Bookable Vacation Homes in Windsor Hills
Over 1539+
Instantly Bookable Vacation Homes in or Near Windsor Hills
House
8.0
(
49 Reviews
)
1 Bedroom
1 Bathroom
-
Private Pool
-
Pool
-
Balcony/Terrace
-
Kitchen
US $572
/Night
7 Nights - $4,004
House
10.0
(
121 Reviews
)
3 Bedrooms
3 Bathrooms
6 Guests
1487 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $202
/Night
7 Nights - $1,417
Condo
9.6
(
95 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1081 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $257
/Night
7 Nights - $1,801
House
9.4
(
214 Reviews
)
6 Bedrooms
4 Bathrooms
15 Guests
3750 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $323
/Night
7 Nights - $2,261
Condo
8.8
(
94 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1450 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $219
/Night
7 Nights - $1,536
House
9.6
(
161 Reviews
)
6 Bedrooms
3 Bathrooms
14 Guests
3000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $439
/Night
7 Nights - $3,073
House
9.4
(
268 Reviews
)
6 Bedrooms
4 Bathrooms
14 Guests
3400 ft²
-
Child Friendly
US $324
/Night
7 Nights - $2,269
Condo
9.4
(
78 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1246 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $201
/Night
7 Nights - $1,408
About Windsor Hills Vacation Rentals
With more than 417 Windsor Hills vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Estiavillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windsor Hills.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas 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 are 2182.89 ft² on average, with prices averaging US $415 a night.
Estiavillas 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.
Use these Quick Filters to Find a Vacation Rental in Windsor Hills
★ Pro Tip: Estiavillas makes it easy to compare the best listings on Estiavillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Estiavillas 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
Windsor Hills Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Windsor Hills?
There are a lot of options in Windsor Hills. If you plan on staying in the Windsor Hills area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor Hills:
- Mickeys Magical Villa Disney Five Star Pool Villa Home at Windsor Hills
- Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
- Welcome to The Windsor Dream!
- Welcome to The Windsor Fantasy!
- Windsor Hills Premium MDM 5/5 Lake View Home w/South Pool - 2 mi from Disney
- 6 bed South Facing Pool/Spa Home Free Heat, Disney
- Cinderella Pool Villa - 10 minutes from Disney
- Windsor Hills Premium MDM 4/4 Lake View Home w/South-Facing Pool-Near Disney
- 6 Bedroom Resort Home, private pool/spa, FREE Heat
- Harry Potter Villa - 10 Mins to Disney
How many vacation rentals have private pools in Windsor Hills?
There are 1181 vacation rentals with private pools near Windsor Hills. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Windsor Hills are best for families?
If you are looking for a family-friendly vacation home in Windsor Hills, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windsor Hills:
How many vacation rentals are available in Windsor Hills?
Currently, the total number of properties listed in 2026 is over 417 in the Windsor Hills area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windsor Hills.
