New
Cottage
2 Bedrooms
4 Guests
Private Pool
Pool
Ocean View
Balcony/Terrace
US $398/Night
7 Nights - US $2,786
Windward Side Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Windward Side
US $126/Night
7 Nights - US $882
US $95/Night
7 Nights - US $665
Villa
10.0(7 Reviews)
3 Bedrooms
6 Guests
- Private Pool
Breakfast
Parking- Pool
US $1,011/Night
7 Nights - US $7,076
US $143/Night
7 Nights - US $1,001
Villa
10.0(4 Reviews)
2 Bedrooms
6 Guests
- Private Pool
Oceanfront- Parking
- Pool
US $770/Night
7 Nights - US $5,390
House
10.0(4 Reviews)
2 Bedrooms
4 Guests
- Balcony/Terrace
Kitchen
Air Conditioner
Internet
US $339/Night
7 Nights - US $2,371
Villa
5.0(2 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $428/Night
7 Nights - US $2,996
House
5.0(2 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $247/Night
7 Nights - US $1,729
Luxury Holiday Rentals in Windward Side
Over 15+ Luxury Holiday Rentals in or Near Windward Side
US $416/Night
7 Nights - US $2,911
US $1,012/Night
7 Nights - US $7,087
US $685/Night
7 Nights - US $4,795
Villa
5.0(1 Review)
3 Bedrooms
6 Guests
Pet Friendly
Child Friendly
US $443/Night
7 Nights - US $3,102
Villa
4.9(59 Reviews)
3 Bedrooms
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $401/Night
7 Nights - US $2,807
Villa
4.9(9 Reviews)
5 Bedrooms
12 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $380/Night
7 Nights - US $2,660
House
4.7(3 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Pool
- Kitchen
Bedding/Linens
US $375/Night
7 Nights - US $2,625
US $360/Night
7 Nights - US $2,520
US $255/Night
7 Nights - US $1,788
Top-Rated Holiday Rentals with a Pool in Windward Side
Over 2+ The Best Private Villas and Holiday Rentals in Windward Side with a Pool
US $129/Night
7 Nights - US $903
Cottage
4.8(27 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $210/Night
7 Nights - US $1,470
Pet-Friendly Holiday Rentals in Windward Side
Over 1+ Pet-Friendly Holiday Rentals in or Near Windward Side
Cottage
1 Bedroom
2 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Pet Friendly
US $146/Night
7 Nights - US $1,022
Windward Side Private Villas and Holiday Homes Under $200
Over 3+ Windward Side Private Villas and Holiday Homes Under $200
Cottage
5.0(2 Reviews)
2 Bedrooms
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $189/Night
7 Nights - US $1,323
Bed & Breakfast
4.7(72 Reviews)
1 Bedroom
- Balcony/Terrace
- Child Friendly
Laundry
US $105/Night
7 Nights - US $733
Cottage
1 Bedroom
2 Guests
- Air Conditioner
- Child Friendly
- Laundry
- Bedding/Linens
US $165/Night
7 Nights - US $1,155
Book a Last Minute Place to Stay in Windward Side
About Casai's Private Villas and Holiday Rentals in Windward Side
Discover more than 24 vacation rentals available in Windward Side. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windward Side.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windward Side, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windward Side. On average, places to stay near Windward Side offer 350.93 ft², with nightly prices averaging US $368.
With Casai, finding and comparing holiday rentals in Windward Side is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Windward Side, BQ
There are 24 Windward Side, BQ Holiday Rentals
- Prices for a holiday home in Windward Side start at US $126
- Top rated vacation home in Windward Side is El Momo Cottages
- Most popular short term in Windward Side is El Momo Cottages
- Cheapest place to stay in Windward Side is El Momo Cottages
- Most expensive holiday rental in Windward Side is Scenery Hotel Saba
Recently Booked Holiday Rentals in Windward Side
Frequently Asked Questions About Windward Side?
What are the top holiday rentals in Windward Side?
With numerous options available in Windward Side, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Windward Side:
- El Momo Cottages
- Saba Arawak Hotel
- Scenery Hotel Saba
- Compass Cottage: Breathtaking Views on Saba, the Caribbean’s “Unspoiled Queen”
- Haiku House, an amazing wooden villa situated in a tropical forest
- Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
- Beautiful Traditional Saba Cottage With all the Modern Amenities
- El Momo Cottages
- Saba Arawak Hotel
- Queen’s hotel, bar & kitchen
How many Casai.nz holiday rentals are available in Windward Side?
As of 2026, Casai boasts over 24 properties listed in the Windward Side area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windward Side.
