Estia Villas - Vacation Rentals in Windward Cay
Villa
10.0
(
224 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
1750 ft²
-
Private Pool -
Hot Tub -
Parking -
Pool
US $248
/Night
7 Nights - $1,736
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
(
2 Reviews
)
1 Bedroom
1 Bathroom
-
Parking
-
Pool
-
Balcony/Terrace -
View
US $970
/Night
7 Nights - $6,792
Villa
9.6
(
195 Reviews
)
4 Bedrooms
4 Bathrooms
10 Guests
2794 ft²
-
Private Pool
-
Oceanfront -
Hot Tub
-
Parking
US $262
/Night
7 Nights - $1,833
Villa
9.6
(
88 Reviews
)
5 Bedrooms
4 Bathrooms
11 Guests
2902 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $318
/Night
7 Nights - $2,223
Villa
9.8
(
51 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
1900 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $295
/Night
7 Nights - $2,066
Villa
9.6
(
144 Reviews
)
6 Bedrooms
5 Bathrooms
12 Guests
2827 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $352
/Night
7 Nights - $2,467
Villa
9.4
(
138 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
1600 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $232
/Night
7 Nights - $1,626
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Luxury Places to Stay in Windward Cay
Over 10000+
Luxury Places to Stay in or Near Windward Cay
Villa
8.0
(
2 Reviews
)
5 Bedrooms
5 Bathrooms
14 Guests
3000 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
Unlock the Best Price
House
8.8
(
11 Reviews
)
6 Bedrooms
5 Bathrooms
17 Guests
3100 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
Unlock the Best Price
House
1 Bedroom
2 Bathrooms
6 Guests
-
Parking
-
Pool
-
Air Conditioner
-
Internet
US $8,499
/Night
7 Nights - $59,494
House
6 Bedrooms
6 Bathrooms
16 Guests
3455.22 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $5,900
/Night
7 Nights - $41,300
House
10 Bedrooms
8 Bathrooms
20 Guests
4273.27 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $5,900
/Night
7 Nights - $41,300
House
56 Bedrooms
56 Bathrooms
26212 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $5,290
/Night
7 Nights - $37,033
House
56 Bedrooms
56 Bathrooms
26228 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $4,526
/Night
7 Nights - $31,679
House
11 Bedrooms
11 Bathrooms
16 Guests
-
Internet
-
Child Friendly
-
Security/Safety
US $3,857
/Night
7 Nights - $26,997
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
(
273 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1797 ft²
-
Parking
-
Pool
-
Ocean View -
Balcony/Terrace
US $126
/Night
7 Nights - $880
Condo
10.0
(
240 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1300 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $238
/Night
7 Nights - $1,666
House
10.0
(
191 Reviews
)
4 Bedrooms
3 Bathrooms
9 Guests
2003 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $447
/Night
7 Nights - $3,131
House
10.0
(
143 Reviews
)
5 Bedrooms
5 Bathrooms
12 Guests
33164 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $378
/Night
7 Nights - $2,649
House
10.0
(
141 Reviews
)
5 Bedrooms
5 Bathrooms
12 Guests
33164 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $298
/Night
7 Nights - $2,086
House
10.0
(
112 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
1914 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $310
/Night
7 Nights - $2,171
House
10.0
(
110 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $309
/Night
7 Nights - $2,166
Condo
10.0
(
99 Reviews
)
3 Bedrooms
2 Bathrooms
9 Guests
1428 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $257
/Night
7 Nights - $1,797
Pet-Friendly Vacation Rentals in Windward Cay
Over 2128+
Pet-Friendly Vacation Rentals in or Near Windward Cay
House
9.6
(
64 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1300 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $191
/Night
7 Nights - $1,340
House
7.0
(
1 Review
)
4 Bedrooms
3 Bathrooms
8 Guests
1636.11 ft²
-
Parking
-
Pool
-
Air Conditioner
-
Internet
US $216
/Night
7 Nights - $1,512
US $606
/Night
7 Nights - $4,240
House
8.2
(
51 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Private Pool
-
Parking
-
Pool
-
Kitchen
US $282
/Night
7 Nights - $1,976
House
9.4
(
9 Reviews
)
4 Bedrooms
3 Bathrooms
10 Guests
1914 ft²
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $322
/Night
7 Nights - $2,255
House
9.0
(
51 Reviews
)
7 Bedrooms
4 Bathrooms
16 Guests
2800 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $353
/Night
7 Nights - $2,469
House
9.8
(
109 Reviews
)
3 Bedrooms
2 Bathrooms
7 Guests
1500 ft²
-
Private Pool
-
Parking
-
Pool
-
Ocean View
US $260
/Night
7 Nights - $1,823
Villa
9.6
(
82 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Private Pool
-
Parking
-
Pool
-
Kitchen
US $201
/Night
7 Nights - $1,407
See More Pet-Friendly Vacation Rentals in Windward Cay on PetFriendly.io
Large Vacation Homes & Villas in Windward Cay
Over 8938+
Large Vacation Homes & Villas in or Near Windward Cay
House
9.6
(
292 Reviews
)
4 Bedrooms
2 Bathrooms
10 Guests
1700 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $206
/Night
7 Nights - $1,444
House
7.4
(
19 Reviews
)
4 Bedrooms
4 Bathrooms
12 Guests
1001.04 ft²
-
Hot Tub
-
Breakfast -
Parking
-
Pool
US $150
/Night
7 Nights - $1,050
Villa
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
-
Pool
-
Kitchen
-
Internet
-
Child Friendly
US $1,166
/Night
7 Nights - $8,159
House
9.6
(
242 Reviews
)
5 Bedrooms
3 Bathrooms
12 Guests
2632 ft²
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $308
/Night
7 Nights - $2,158
House
9.6
(
166 Reviews
)
5 Bedrooms
5 Bathrooms
14 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $400
/Night
7 Nights - $2,801
House
9.0
(
93 Reviews
)
6 Bedrooms
6 Bathrooms
13 Guests
3051 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Pool
US $387
/Night
7 Nights - $2,706
House
9.6
(
278 Reviews
)
6 Bedrooms
4 Bathrooms
12 Guests
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $202
/Night
7 Nights - $1,414
Villa
9.4
(
121 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Child Friendly
-
Security/Safety
US $413
/Night
7 Nights - $2,891
See More Family Vacation Rentals in Windward Cay on FVR
Wheelchair Accessible Vacation Homes in Windward Cay
Over 1852+
Wheelchair Accessible Vacation Homes in or Near Windward Cay
Condo
9.0
(
72 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1253 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $204
/Night
7 Nights - $1,429
House
8.9
(
13 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1194.79 ft²
-
Parking
-
Pool
-
Air Conditioner
-
Internet
US $122
/Night
7 Nights - $854
Condo
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
-
Parking
-
Pool
-
Kitchen
-
Internet
US $507
/Night
7 Nights - $3,549
New
Condo
8.6
(
15 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $249
/Night
7 Nights - $1,742
Apartment
9.8
(
63 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1329 ft²
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
US $171
/Night
7 Nights - $1,198
Condo
7.2
(
5 Reviews
)
2 Bedrooms
2 Bathrooms
5 Guests
1507 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $244
/Night
7 Nights - $1,707
New
Condo
9.4
(
13 Reviews
)
2 Bedrooms
2 Bathrooms
4 Guests
1238 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $354
/Night
7 Nights - $2,481
Apartment
9.0
(
2 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1196 ft²
-
Parking
-
Pool
-
Kitchen
-
Air Conditioner
US $221
/Night
7 Nights - $1,547
Windward Cay Vacation Rentals and Airbnb Places to Stay Under $200
Over 4179+
Windward Cay Vacation Rentals and Airbnb Places to Stay Under $200
Condo
9.8
(
77 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1503 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $195
/Night
7 Nights - $1,364
House
3 Bedrooms
2 Bathrooms
6 Guests
107.64 ft²
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Internet
US $100
/Night
7 Nights - $700
Apartment
10.0
(
1 Review
)
1 Bedroom
1 Bathroom
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Child Friendly
US $140
/Night
7 Nights - $983
Apartment
9.4
(
45 Reviews
)
2 Bedrooms
2 Bathrooms
7 Guests
1142 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $179
/Night
7 Nights - $1,253
Condo
9.6
(
210 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1200 ft²
-
Hot Tub
-
Parking
-
Pool
-
Ocean View
US $165
/Night
7 Nights - $1,152
House
9.6
(
97 Reviews
)
4 Bedrooms
4 Bathrooms
8 Guests
1852 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $176
/Night
7 Nights - $1,234
House
9.0
(
31 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
1300 ft²
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
US $144
/Night
7 Nights - $1,010
House
8.6
(
115 Reviews
)
3 Bedrooms
2 Bathrooms
6 Guests
-
Parking
-
Pool
-
Kitchen
-
Air Conditioner
US $161
/Night
7 Nights - $1,128
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Instantly Bookable Vacation Homes in Windward Cay
Over 10441+
Instantly Bookable Vacation Homes in or Near Windward Cay
House
9.8
(
163 Reviews
)
4 Bedrooms
2 Bathrooms
8 Guests
-
Private Pool
-
Parking
-
Pool
-
Balcony/Terrace
US $260
/Night
7 Nights - $1,820
Villa
10.0
(
24 Reviews
)
1 Bedroom
1 Bathroom
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $178
/Night
7 Nights - $1,249
House
8.8
(
124 Reviews
)
2 Bedrooms
2 Bathrooms
8 Guests
1150 ft²
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $238
/Night
7 Nights - $1,664
House
8.6
(
78 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
1905 ft²
-
Pool
-
Kitchen
-
Air Conditioner
-
Internet
US $331
/Night
7 Nights - $2,318
House
9.6
(
33 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
US $233
/Night
7 Nights - $1,631
House
9.8
(
114 Reviews
)
3 Bedrooms
2 Bathrooms
8 Guests
1200 ft²
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
US $261
/Night
7 Nights - $1,825
House
9.8
(
80 Reviews
)
4 Bedrooms
3 Bathrooms
8 Guests
2038 ft²
-
Private Pool
-
Oceanfront
-
Hot Tub
-
Parking
US $254
/Night
7 Nights - $1,775
House
9.4
(
225 Reviews
)
2 Bedrooms
2 Bathrooms
6 Guests
1200 ft²
-
Hot Tub
-
Parking
-
Pool
-
Spa
US $212
/Night
7 Nights - $1,485
About Windward Cay Vacation Rentals
With more than 2434 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 1802.83 ft² on average, with prices averaging US $515 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 | 2165 |
| Vacation Homes | 216 |
| 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:
- Delightful modern 4 bed, 3 bath villa with private pool/spa and lake view.
- Private Pool & Spa Only 8 mi to Disney! Gated Community
- Disney at 15 min - lake view villa - private pool - gated Lake Berkley Resort
- 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 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
How many vacation rentals have private pools in Windward Cay?
There are 6863 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 2434 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.
