A coastal landscape with clear blue ocean, green hills, and palm trees.

Windy Hill Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Windy Hill vacation rentals

Exterior

1. Malfranza Apartments

Malfranza Apartments
3.0 star property
Bridgetown
9.0 out of 10, Wonderful, (96 reviews)
"Great host and accomodations but the noise from the highway was a bit too much for me."
United States
Marc Downing
$78 nightly
The price is $93
Sep 22 - Sep 23
Total with taxes and fees
Malfranza Apartments
Cafe

2. The Palms Resort

The Palms Resort
3.0 star property
Holetown
8.6 out of 10, Excellent, (234 reviews)
"The room was extremely clean and comfortable the pictures don’t do it justice it’s so pretty in person I recommend you stay at this resort it’s close to the beach supermarket and a lot of restaurants book your stay here!"
United States
Christine
$111 nightly
The price is $128
Oct 16 - Oct 17
Total with taxes and fees
The Palms Resort
Terrace/patio

3. BEYOND IMAGINATION

BEYOND IMAGINATION
St. Thomas
8.0 out of 10, Very good, (1 review)
"Great communication with the host. Nicole ensured that we will get to the property by offering a taxi service which was very convenient as we flew in after midnight. She checked on us during the stay. The house is licated in a very quiet area. Shirt drive/bus ride to the nearest gas station/store. I recommend it for a short stay. "
United States
Neta
$85 nightly
The price is $85
Sep 28 - Sep 29
Total with taxes and fees
BEYOND IMAGINATION
Outdoor pool, sun loungers

4. All Seasons Resort - Europa

All Seasons Resort - Europa
3.0 star property
Holetown
8.8 out of 10, Excellent, (95 reviews)
"Staff amazing Property amazing Rooms amazingly clean Location location access to everything"
United States
Tessa
$151 nightly
The price is $171
Sep 22 - Sep 23
Total with taxes and fees
All Seasons Resort - Europa
Property entrance

5. Manderley Villas

Manderley Villas
3.0 star property
Mangrove
9.4 out of 10, Exceptional, (105 reviews)
"Host was great, I enjoyed my stay "
United States
STEPHIAN
$79 nightly
The price is $96
Oct 22 - Oct 23
Total with taxes and fees
Manderley Villas
View from property

6. Ocean Spray Apartments

Ocean Spray Apartments
3.0 star property
Inch Marlowe
7.4 out of 10, Good, (545 reviews)
"Very comfortable very efficient and polite staff great value excellent stay"
United States
Gina
$63 nightly
The price is $80
Sep 23 - Sep 24
Total with taxes and fees
Ocean Spray Apartments
Sun loungers, beach towels

7. Breezy Vistas, Terrace – Saint James One‑Bedroom, Sea Breeze, WiFi & Parking

Breezy Vistas, Terrace – Saint James One‑Bedroom, Sea Breeze, WiFi & Parking
Westmoreland St James Barbados
9.0 out of 10, Wonderful, (4 reviews)
"Cozy quiet space Privacy Bedroom blackout ready if you want to sleep in. Kitchen equipment to prepare a meal We enjoyed our stay Thank you"
United States
Peter
$152 nightly
The price is $152
Oct 5 - Oct 6
Total with taxes and fees
Breezy Vistas, Terrace – Saint James One‑Bedroom, Sea Breeze, WiFi & Parking
Outdoor pool, pool umbrellas, sun loungers

8. Sea Symphony Villa

Sea Symphony Villa
3.5 star property
Fryers Well
8.6 out of 10, Excellent, (11 reviews)
"The staff was wonderful, chef made delicious Bajan meals, very accommodating and pleasant stay…will definitely be back- thank you for a relaxing stress free birthday vacation! "
United States
DOMINIQUE
$322 nightly
The price is $358
Oct 21 - Oct 22
Total with taxes and fees
Sea Symphony Villa
Condo, 2 Bedrooms, Balcony, Garden View | Beach | Beach nearby

9. Kingsgate #1 - by Zenbreak

Kingsgate #1 - by Zenbreak
4.0 star property
Gibbes
10.0 out of 10, Exceptional, (2 reviews)
"My only critique is that they need four new beach chairs, preferably the Tommy Bahama chairs. They are light, comfortable, and sturdy. Other than that, it was great and thank you!"
United States
John
$283 nightly
The price is $312
Oct 6 - Oct 7
Total with taxes and fees
Kingsgate #1 - by Zenbreak
Interior

10. Seacruise Villa

Seacruise Villa
3.5 star property
Fryers Well
9.8 out of 10, Exceptional, (9 reviews)
"Everything was up to Par and they were very accommodating to my Birthday Celebration 🎂 🎈 🎉 🎁 I Thank Everyone For there Hospitality"
United States
Lisa
$252 nightly
The price is $277
Oct 20 - Oct 21
Total with taxes and fees
Seacruise Villa
Apartment | 2 bedrooms, iron/ironing board, WiFi (free)

11. The Terraces at Mangrove

The Terraces at Mangrove
2.0 star property
Mangrove
9.8 out of 10, Exceptional, (10 reviews)
"Clean, comfortable and close ro the airport"
Canada
Alison
$81 nightly
The price is $97
Sep 22 - Sep 23
Total with taxes and fees
The Terraces at Mangrove
Smart TV, DVD player

12. Cozy 1-bedroom apartment in delightful St. George with WiFi

Cozy 1-bedroom apartment in delightful St. George with WiFi
Bridgetown
10.0 out of 10, Exceptional, (5 reviews)
"Nice host and very responsive and the house was clean."
Canada
Wedad
$135 nightly
The price is $135
Sep 22 - Sep 23
Total with taxes and fees
Cozy 1-bedroom apartment in delightful St. George with WiFi
Outdoor pool

13. THE Cottage, Saint Davids, Christ Church, Barbados

THE Cottage, Saint Davids, Christ Church, Barbados
3.0 star property
Oistins
9.4 out of 10, Exceptional, (15 reviews)
"The privacy & seclusion of this guest house & pool is amazing! Its a perfect little spot with all the amenities you need and more! Owner Mark and Property Manager George were fantastic to deal with and very prompt in responses. Location is great ..close to water and especially to Oistins! Would highly recomment checking this place out ..I know I will again."
Canada
Sean
$149 nightly
The price is $180
Sep 24 - Sep 25
Total with taxes and fees
THE Cottage, Saint Davids, Christ Church, Barbados
Beach

14. Little Diamond Jungle Home, Panoramic Ocean Views, 2 Verandas &Tropical Garden

Little Diamond Jungle Home, Panoramic Ocean Views, 2 Verandas &Tropical Garden
Saint Joseph
9.8 out of 10, Exceptional, (8 reviews)
"I cannot recommend this property enough. The view from the patio is beautiful, and Jacob responded to all our questions quickly. We felt very safe, and all the locals were friendly. I would definitely stay here again! "
United States
Ashley B.
$434 nightly
The price is $434
Oct 11 - Oct 12
Total with taxes and fees
Little Diamond Jungle Home, Panoramic Ocean Views, 2 Verandas &Tropical Garden
Apartment, 1 Bedroom (Garnet) | Iron/ironing board, WiFi (free), bed sheets

15. Jem Gems

Jem Gems
2.5 star property
Durants
9.4 out of 10, Exceptional, (25 reviews)
"Th room were spacious and nice "
United States
Laurence
$56 nightly
The price is $67
Oct 22 - Oct 23
Total with taxes and fees
Jem Gems
In-room safe, cribs (free), WiFi (free), bed sheets

16. Blue Haven Holiday Apartments

Blue Haven Holiday Apartments
3.0 star property
St. Lawrence Gap
9.6 out of 10, Exceptional, (336 reviews)
"I definitely recommend here as a good place to stay!!"
United States
Raymond
$101 nightly
The price is $115
Oct 5 - Oct 6
Total with taxes and fees
Blue Haven Holiday Apartments
Studio, Beach View | Beach

17. Ocean View Rockley by BLR

Ocean View Rockley by BLR
3.0 star property
Rockley
8.0 out of 10, Very good, (4 reviews)
"It was okay it was clean and very handy for the beach and the shops, welcome"
United Kingdom
Stacia Roxanne Ward John William
$59 nightly
The price is $71
Oct 21 - Oct 22
Total with taxes and fees
Ocean View Rockley by BLR
Exterior

18. Condo in Bridgetown

Condo in Bridgetown
Bridgetown
$143 nightly
The price is $143
Sep 22 - Sep 23
Total with taxes and fees
Condo in Bridgetown
Beach nearby, white sand, beach towels

19. BLR Villas Dover Beach

BLR Villas Dover Beach
4.0 star property
St. Lawrence Gap
7.6 out of 10, Good, (65 reviews)
"The room was clean and the location convenient for exploring."
United Kingdom
Michelangelo
$57 nightly
The price is $68
Sep 30 - Oct 1
Total with taxes and fees
BLR Villas Dover Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windy Hill Hotel Reviews

Waves Resort & Spa, Barbados, An Autograph Collection® All-Inclusive Resort

Waves Resort & Spa, Barbados, An Autograph Collection® All-Inclusive Resort

10/10 Excellent
"Absolutely loved our stay!! The ocean front view was beautiful to see every morning. I loved every second of our visit we will definitely be staying again! The room was very cleaned, the staff were so helpful and kind. The only thing I would say was getting the 2 twin beds combined into a king was alittle uncomfortable but we made it work :) Overall 10/10"
Eryan 6-night trip
Posted 4 hours ago
Waves Resort & Spa, Barbados, An Autograph Collection® All-Inclusive Resort

Find out more about Windy Hill

Everything you need to know about Windy Hill vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windy Hill vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windy Hill vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windy Hill vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windy Hill. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windy Hill in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $68 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windy Hill rentals

At Expedia, we put the best Windy Hill vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windy Hill rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windy Hill vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windy Hill. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Windy Hill?

Yes, we give you a choice of vacation rentals near the most popular local attractions in Windy Hill, or you can choose a more secluded option if you want a relaxing place to stay. Nature enthusiasts will enjoy the beaches in Windy Hill. Make sure you have time to check out the restaurants while you're in the area.

What's the top vacation rental that Windy Hill has to offer?

The Gem - by Zenbreak: Located near Windy Hill, this vacation home rental comes with free WiFi so you can feel at home during your trip.

What’s there to see and do in Windy Hill?

Explore the area and family-friendly sights such as Oistin's Friday Night Fish Fry, or get out into nature at a spot like Bathsheba Beach. In the larger area, you’ll find Harrison's Cave and Royal Westmoreland Golf Course.

What’s a vacation rental in Windy Hill like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Windy Hill. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family trip.