Estia Villas - Vacation Rentals in Windward Cay
Villa
9.8
(
219 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
1750 ft²
-
Private Pool -
Hot Tub -
Fireplace/Heating -
Pool
US $247
/Night
7 Nights - $1,732
Villa
8.0
(
3 Reviews
)
1 Bedroom
1 Bathroom
10 Guests
-
Parking -
Air Conditioner -
Internet -
Child Friendly
US $156
/Night
7 Nights - $1,092
Villa
10.0
(
24 Reviews
)
1 Bedroom
1 Bathroom
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $178
/Night
7 Nights - $1,249
Villa
9.6
(
88 Reviews
)
5 Bedrooms
4 Bathrooms
11 Guests
2902 ft²
-
Private Pool
-
Hot Tub
-
Pool
-
Ocean View
US $334
/Night
7 Nights - $2,341
Villa
9.8
(
51 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1900 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $293
/Night
7 Nights - $2,053
Villa
9.6
(
142 Reviews
)
6 Bedrooms
5 Bathrooms
13 Guests
2827 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $299
/Night
7 Nights - $2,093
Villa
9.4
(
133 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
1600 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $180
/Night
7 Nights - $1,259
Villa
9.0
(
63 Reviews
)
4 Bedrooms
4 Bathrooms
12 Guests
2061 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $264
/Night
7 Nights - $1,851
See More Windward Cay Vacation Rentals
Luxury Places to Stay in Windward Cay
Over 10000+
Luxury Places to Stay in or Near Windward Cay
House
8.8
(
11 Reviews
)
6 Bedrooms
5 Bathrooms
17 Guests
3100 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
Unlock the Best Price
6 Bedrooms
6 Bathrooms
16 Guests
3455.22 ft²
-
Hot Tub
-
Pool
-
Balcony/Terrace
-
Pet Friendly
US $5,900
/Night
7 Nights - $41,300
10 Bedrooms
8 Bathrooms
20 Guests
4273.27 ft²
-
Hot Tub
-
Pool
-
Balcony/Terrace
-
Pet Friendly
US $5,900
/Night
7 Nights - $41,300
House
3 Bedrooms
2 Bathrooms
6 Guests
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
View
US $5,746
/Night
7 Nights - $40,220
House
56 Bedrooms
56 Bathrooms
26228 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $4,792
/Night
7 Nights - $33,545
House
8.8
(
3 Reviews
)
9 Bedrooms
5 Bathrooms
22 Guests
1722 ft²
-
Private Pool
-
Hot Tub
-
Pool
-
Balcony/Terrace
US $4,174
/Night
7 Nights - $29,216
Villa
15 Bedrooms
15 Bathrooms
30 Guests
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $4,104
/Night
7 Nights - $28,725
Villa
15 Bedrooms
15 Bathrooms
32 Guests
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $3,953
/Night
7 Nights - $27,671
See More Windward Cay Luxury Vacation Rentals
Find More Windward Cay Villas, Resorts, & Rentals on BedroomVillas
Top-Rated Vacation Rentals with a Pool in Windward Cay
Over 10000+
Top-Rated Vacation Rentals with a Pool in or Near Windward Cay
House
10.0
(
263 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1797 ft²
-
Fireplace/Heating
-
Pool
-
Ocean View
-
Balcony/Terrace
US $157
/Night
7 Nights - $1,097
Condo
10.0
(
233 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1300 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Ocean View
US $126
/Night
7 Nights - $879
House
10.0
(
189 Reviews
)
4 Bedrooms
3 Bathrooms
9 Guests
2003 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $324
/Night
7 Nights - $2,269
House
10.0
(
135 Reviews
)
5 Bedrooms
5 Bathrooms
12 Guests
33164 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $280
/Night
7 Nights - $1,960
House
10.0
(
134 Reviews
)
5 Bedrooms
5 Bathrooms
12 Guests
33164 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $321
/Night
7 Nights - $2,250
Apartment
10.0
(
115 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
14305 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $208
/Night
7 Nights - $1,459
House
10.0
(
108 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
1914 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $226
/Night
7 Nights - $1,579
House
10.0
(
107 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1450 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $194
/Night
7 Nights - $1,356
Pet-Friendly Vacation Rentals in Windward Cay
Over 2075+
Pet-Friendly Vacation Rentals in or Near Windward Cay
7.0
(
1 Review
)
4 Bedrooms
3 Bathrooms
8 Guests
1636.11 ft²
-
Pool
-
Pet Friendly
-
Parking
-
Air Conditioner
US $216
/Night
7 Nights - $1,512
House
9.6
(
64 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1300 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $188
/Night
7 Nights - $1,318
US $610
/Night
7 Nights - $4,272
House
8.2
(
50 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Pet Friendly
US $247
/Night
7 Nights - $1,728
House
9.0
(
51 Reviews
)
7 Bedrooms
4 Bathrooms
16 Guests
2800 ft²
-
Private Pool
-
Hot Tub
-
Spa -
Fireplace/Heating
US $363
/Night
7 Nights - $2,538
House
9.8
(
107 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1500 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Ocean View
US $271
/Night
7 Nights - $1,898
Villa
9.6
(
80 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Pet Friendly
US $212
/Night
7 Nights - $1,482
House
10.0
(
1 Review
)
4 Bedrooms
3 Bathrooms
8 Guests
1914 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $241
/Night
7 Nights - $1,690
See More Pet-Friendly Vacation Rentals in Windward Cay on PetFriendly.io
Large Vacation Homes & Villas in Windward Cay
Over 8885+
Large Vacation Homes & Villas in or Near Windward Cay
7.4
(
19 Reviews
)
4 Bedrooms
4 Bathrooms
12 Guests
1001.04 ft²
-
Hot Tub
-
Pool
-
Balcony/Terrace
-
Breakfast
US $150
/Night
7 Nights - $1,050
House
9.6
(
288 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
1700 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $184
/Night
7 Nights - $1,285
House
10.0
(
4 Reviews
)
5 Bedrooms
5 Bathrooms
11 Guests
3254 ft²
-
Private Pool
-
Hot Tub
-
Pool
-
Kitchen
US $450
/Night
7 Nights - $3,149
House
9.6
(
240 Reviews
)
5 Bedrooms
3 Bathrooms
12 Guests
2632 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $254
/Night
7 Nights - $1,776
House
9.0
(
91 Reviews
)
6 Bedrooms
6 Bathrooms
13 Guests
3051 ft²
-
Private Pool
-
Oceanfront -
Hot Tub
-
Pool
US $352
/Night
7 Nights - $2,462
House
9.6
(
273 Reviews
)
6 Bedrooms
4 Bathrooms
12 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $185
/Night
7 Nights - $1,295
Villa
9.2
(
99 Reviews
)
7 Bedrooms
5 Bathrooms
15 Guests
3000 ft²
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $405
/Night
7 Nights - $2,838
House
8.6
(
17 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
1914 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Kitchen
US $226
/Night
7 Nights - $1,581
See More Family Vacation Rentals in Windward Cay on FVR
Wheelchair Accessible Vacation Homes in Windward Cay
Over 1723+
Wheelchair Accessible Vacation Homes in or Near Windward Cay
8.9
(
13 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1194.79 ft²
-
Pool
-
Parking
-
Air Conditioner
-
Internet
US $122
/Night
7 Nights - $854
House
9.2
(
9 Reviews
)
4 Bedrooms
3 Bathrooms
15 Guests
2110 ft²
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $355
/Night
7 Nights - $2,483
8.4
(
2737 Reviews
)
1 Bathroom
-
Hot Tub
-
Pool
-
Balcony/Terrace
-
Breakfast
US $119
/Night
7 Nights - $832
Condo
9.0
(
72 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1253 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $183
/Night
7 Nights - $1,284
Apartment
9.8
(
63 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1119 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $177
/Night
7 Nights - $1,239
Apartment
9.0
(
2 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1196 ft²
-
Fireplace/Heating
-
Pool
-
Kitchen
-
Parking
US $216
/Night
7 Nights - $1,512
Apartment
8.6
(
16 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1329 ft²
-
Fireplace/Heating
-
Pool
-
Kitchen
-
Parking
US $172
/Night
7 Nights - $1,204
Condo
10.0
(
98 Reviews
)
3 Bedrooms
2 Bathrooms
9 Guests
1428 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $172
/Night
7 Nights - $1,207
Windward Cay Vacation Rentals and Airbnb Places to Stay Under $200
Over 4841+
Windward Cay Vacation Rentals and Airbnb Places to Stay Under $200
3 Bedrooms
2 Bathrooms
6 Guests
107.64 ft²
-
Balcony/Terrace
-
Parking
-
Air Conditioner
-
Internet
US $100
/Night
7 Nights - $700
House
9.8
(
113 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1200 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $165
/Night
7 Nights - $1,152
House
6.8
(
71 Reviews
)
1 Bedroom
1 Bathroom
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Kitchen
US $68
/Night
7 Nights - $477
Apartment
9.4
(
43 Reviews
)
2 Bedrooms
2 Bathrooms
7 Guests
1142 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $170
/Night
7 Nights - $1,187
Condo
9.6
(
207 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1200 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Ocean View
US $136
/Night
7 Nights - $953
House
9.6
(
96 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
1852 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $163
/Night
7 Nights - $1,141
House
9.2
(
115 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1300 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Ocean View
US $152
/Night
7 Nights - $1,064
House
9.0
(
31 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1300 ft²
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
-
Kitchen
US $144
/Night
7 Nights - $1,005
See More Windward Cay Vacation Rental Deals
Instantly Bookable Vacation Homes in Windward Cay
Over 10320+
Instantly Bookable Vacation Homes in or Near Windward Cay
House
9.8
(
158 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Private Pool
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $254
/Night
7 Nights - $1,781
House
10.0
(
3 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
16146 ft²
-
Fireplace/Heating
-
Balcony/Terrace
-
Kitchen
-
Parking
US $317
/Night
7 Nights - $2,216
House
9.0
(
122 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
1150 ft²
-
Hot Tub
-
Spa
-
Fireplace/Heating
-
Pool
US $279
/Night
7 Nights - $1,950
House
8.6
(
78 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
1905 ft²
-
Fireplace/Heating
-
Pool
-
Kitchen
-
Air Conditioner
US $316
/Night
7 Nights - $2,212
House
9.6
(
33 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Private Pool
-
Hot Tub
-
Fireplace/Heating
-
Pool
US $228
/Night
7 Nights - $1,593
House
9.8
(
80 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
2038 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Spa
US $256
/Night
7 Nights - $1,793
Condo
9.8
(
77 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1503 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $204
/Night
7 Nights - $1,431
Condo
9.4
(
47 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1667 ft²
-
Hot Tub
-
Fireplace/Heating
-
Pool
-
Balcony/Terrace
US $220
/Night
7 Nights - $1,539
About Windward Cay Vacation Rentals
With more than 2403 Windward Cay 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 Windward Cay.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Estiavillas Windward Cay, 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 Windward Cay. Places to stay near Windward Cay are 1700.22 ft² on average, with prices averaging US $517 a night.
Estiavillas makes it easy and safe to find and compare vacation rentals in Windward Cay 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 Windward Cay
| Type | Count |
|---|---|
| Villas | 2132 |
| Vacation Homes | 218 |
| Holiday Apartments | 51 |
| Hotels | 1 |
| Resorts | 1 |
Use these Quick Filters to Find a Vacation Rental in Windward Cay
★ 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 Windward Cay.
Weather in Windward Cay
View the weather forecast for Windward Cay before booking your Windward Cay 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
Windward Cay Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Windward Cay?
There are a lot of options in Windward Cay. If you plan on staying in the Windward Cay area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windward Cay:
- Private Pool & Spa Only 8 mi to Disney! Gated Community
- Once Upon A Time@Storey Lake-9 Bedroom Disney Haven w/Game Room & Private Pool!
- 6 Bedroom Themed Villa Near Disney World with private Pool & Spot, Game Room
- South facing pool & spa on water conservation area in gated community
- Spacious Bowling 14BR 14.5BA, Sleeps38, Lake Views
- Luxury Villa Storey Lake, 15min→Disney, private pool + hot tub + No Extra Fees
- Luxury villa with south facing pool; 15 minutes from DisneyWorld
- 'Lakeside Haven' Fantastic South Facing Pool, Spa and Stunning Lakeside Views.
- 10BR Villa Near Disney, Pool and Resort Waterpark
- Incredible 6BR Villa by Disney Private Pool Games
How many vacation rentals have private pools in Windward Cay?
There are 7004 vacation rentals with private pools near Windward Cay. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Windward Cay are best for families?
If you are looking for a family-friendly vacation home in Windward Cay, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windward Cay:
How many vacation rentals are available in Windward Cay?
Currently, the total number of properties listed in 2026 is over 2403 in the Windward Cay area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windward Cay.
