A tropical beach with palm trees, clear blue water, and rocky outcrops.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Windward Islands holiday rentals

Two wooden Adirondack chairs facing a table with a bottle and glass, on a balcony with stone flooring and a view of a mountain.

1. You 4 Ric Piton Suites

You 4 Ric Piton Suites
4.0 star property
Soufriere
10.0 out of 10, Exceptional, (4 reviews)
"This property is simply amazing! If you're looking for a nice quiet, peaceful and restful vacation this is place to be. Excellent views, natural environment and located close to beautiful beaches and restaurants in the town of Soufrier. I fully endorse this place and if it was possible I would give it 10 stars"
United States
Stachio
The price is £114
includes taxes & fees
6 Oct - 7 Oct
You 4 Ric Piton Suites
A tropical resort with a pool, palm trees, and a thatched-roof hut.

2. Vista Del Piton - Your Tropical Escape with Stunning Piton Views !

Vista Del Piton - Your Tropical Escape with Stunning Piton Views !
Castries
9.8 out of 10, Exceptional, (7 reviews)
"Eloi was the best host my wife and I could have asked for! Very caring and helpful guy, drove us to restaurants and excursions around the area which was very helpful! When we arrived, he had fruit and flowers he picked on the table for us! I recommend this place highly!"
United States
matthew p.
The price is £86
includes taxes & fees
6 Oct - 7 Oct
Vista Del Piton - Your Tropical Escape with Stunning Piton Views !
A modern hotel with a swimming pool, outdoor seating, and a multi-story building with balconies.

3. B&B HOME Fort de France Marina

B&B HOME Fort de France Marina
4.0 star property
Fort-de-France
9.0 out of 10, Wonderful, (172 reviews)
"We loved everything."
United Kingdom
Tabitha
The price is £102
includes taxes & fees
6 Oct - 7 Oct
B&B HOME Fort de France Marina
A balcony with a wicker tray holding a wine bottle, a glass, and fruits.

4. Seabliss Villa

Seabliss Villa
3.0 star property
Vieux Fort
8.0 out of 10, Very good, (7 reviews)
"The Seabliss Villa on the South Coast in St Lucia, was the perfect choice and place for us to have spend our vacation this year. The breathtaking scenery, the peaceful and quiet community added to the thorough enjoyment of that place. Each room of that Villa had a story to tell, and I liked that. The place is so warm, cozy, relaxing and welcoming. Thank you Seabliss host, you did an excellent job. I will come again and again."
United States
Cassandra
The price is £115
includes taxes & fees
6 Oct - 7 Oct
Seabliss Villa
A beach with clear blue water, sandy shore, and dense green foliage.

5. Bogles Round House

Bogles Round House
2.5 star property
Hillsborough
8.8 out of 10, Excellent, (74 reviews)
"Perfect for our one night stay and to visit Carriacou. Everything was clean and tidy and access to the property was easy."
United Kingdom
Harvey
The price is £91
includes taxes & fees
8 Oct - 9 Oct
Bogles Round House
A wooden deck with lounge chairs, a small table, and a hammock.

6. The Island Experiences-Samo

The Island Experiences-Samo
Choiseul
8.4 out of 10, Very good, (20 reviews)
"Beautiful place, we thoroughly enjoyed our night there."
United States
Ashley s.
The price is £83
includes taxes & fees
6 Oct - 7 Oct
The Island Experiences-Samo
A modern living room with a white sofa, a dining table with chairs, and a kitchen area with a stove, microwave, and refrigerator.

7. the island experience samo

the island experience samo
3.0 star property
Choiseul
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at this villa in St. Lucia. The host was absolutely amazing—very responsive, kind, and genuinely cared about making sure we had everything we needed throughout our stay. The villa itself is beautiful, modern, and thoughtfully designed. Everything felt clean, well-maintained, and comfortable, with a great balance of style and relaxation. It was the perfect place to unwind and enjoy the island. Overall, it was a fantastic experience, and we would definitely love to come...
United States
Nadezhda
The price is £184
includes taxes & fees
6 Oct - 7 Oct
the island experience samo
A large, two-story building with a red roof and white walls, surrounded by lush greenery and mountains in the background.

8. Comfort Suites- Special

Comfort Suites- Special
Choiseul
9.4 out of 10, Exceptional, (12 reviews)
"The room was exactly as expected and the service provided by the hosts was exceptional"
Canada
HALEY
The price is £56
includes taxes & fees
6 Oct - 7 Oct
Comfort Suites- Special
A view of a coastal town with palm trees and mountains in the background.

9. Samfi Gardens

Samfi Gardens
2.5 star property
Soufrière
9.8 out of 10, Exceptional, (218 reviews)
"It was a awesome place to stay at with a great view. The room was spotless and the staff was great. I highly recommend staying here"
United States
Preston
The price is £124
includes taxes & fees
6 Oct - 7 Oct
Samfi Gardens
A balcony with a table set for breakfast, overlooking a coastal view.

10. Kaouanne

Kaouanne
Pointe du Bout
9.2 out of 10, Wonderful, (115 reviews)
"Great location and friendly staff. Close to beach and restaurants"
United States
Jodiann
The price is £104
includes taxes & fees
11 Oct - 12 Oct
Kaouanne
A balcony with a view of a residential area, a metal railing, and a bench.

11. Agape Suites

Agape Suites
3.0 star property
Soufrière
10.0 out of 10, Exceptional, (19 reviews)
"Amazing boutique apartment, very clean."
Canada
Michael
The price is £100
includes taxes & fees
13 Oct - 14 Oct
Agape Suites
A multi-story building with a blue exterior, a staircase leading to the upper floors, and a garage door.

12. La Bwizan Inn -Apartment #2-

La Bwizan Inn -Apartment #2-
Laborie
9.4 out of 10, Exceptional, (8 reviews)
"This is a beautiful unit & the walkability of the town is amazing. The units kitchen is great for cooking or heating up the leftovers from local eateries. Hosts are delightful and very pleasant."
United States
Christina R.
The price is £85
includes taxes & fees
6 Oct - 7 Oct
La Bwizan Inn -Apartment #2-
A wooden deck with wicker furniture, a pool, and a sign with porch rules.

13. The Island Experience- Melo Newly Listed!!!

The Island Experience- Melo Newly Listed!!!
Choiseul
9.0 out of 10, Wonderful, (34 reviews)
"Great place overall. I loved the fact that this place had a private pool."
United States
Miss K.
The price is £83
includes taxes & fees
6 Oct - 7 Oct
The Island Experience- Melo Newly Listed!!!
A swimming pool with lounge chairs and a thatched umbrella, surrounded by tropical plants and a clear sky.

14. Hotel Panoramic

Hotel Panoramic
3.0 star property
Trois-Ilets
8.6 out of 10, Excellent, (328 reviews)
"Very near beach and small town. Convenient location to beach hop each day in our rental car. "
Canada
Hektor
The price is £89
includes taxes & fees
12 Oct - 13 Oct
Hotel Panoramic
A poolside area with a lounge chair, a glass of drink, and a bottle of wine on a metal table.

15. Toraille Waterfall Villas

Toraille Waterfall Villas
3.5 star property
Soufriere
7.8 out of 10, Good, (7 reviews)
"I would surely visit again . Excellent security, cleanliness, communication was good . We enjoy our one week stay . And it is just next door to the Toraille water falls"
United States
vanda
The price is £124
includes taxes & fees
6 Oct - 7 Oct
Toraille Waterfall Villas
A balcony with a table and chairs, a potted plant, and a view of a hill with trees.

16. Anne's Home Away from Home

Anne's Home Away from Home
Banse
10.0 out of 10, Exceptional, (6 reviews)
"Host was excellent they go out of their way to make guests feel comfortable and welcome."
United States
Keith S.
The price is £87
includes taxes & fees
6 Oct - 7 Oct
Anne's Home Away from Home
A hotel with a swimming pool, outdoor seating area, and a staircase leading to the upper floors.

17. Union Hilltop Paradise Villas

Union Hilltop Paradise Villas
3.5 star property
Castries
9.0 out of 10, Wonderful, (4 reviews)
"The room was very soacious, very clean and the views to die for. Beautiful mornings and evening views of the Caribbean Sea and the property had a hit tub and pool to boost."
United Kingdom
Ayesha Cyrus
The price is £97
includes taxes & fees
11 Oct - 12 Oct
Union Hilltop Paradise Villas
A living room with a beige sofa, a TV on a wooden table, and a balcony with a white railing and potted plants.

18. Sandrati Villa

Sandrati Villa
4.0 star property
Bequia Island
8.8 out of 10, Excellent, (3 reviews)
"Ocean was visible at a distance. Only suitable for older children who can be separate from adult supervision as the rooms are separated and require having to go outside stairs to access each other. Friendly and helpful staff. Location can loud with passing vans, dogs barking. Slight bug problem on ground floor. "
United States
Brandon
The price is £109
includes taxes & fees
15 Oct - 16 Oct
Sandrati Villa
A beach with clear blue water, rocky shoreline, and dense green foliage.

19. Majestic views of Pitons, Caribbean sea, amazing sunsets right from your room

Majestic views of Pitons, Caribbean sea, amazing sunsets right from your room
Choiseul
10.0 out of 10, Exceptional, (3 reviews)
"Our stay at Majestic Views was WONDERFUL!!! Shelba and Mr. Davidson helped us with everything - from Pre Arrival planning to airport transfers, even a birthday celebration execution. They were so warm, kind and attentive to our needs. They made us feel safe and well taken care of! I encourage anyone who wants a home away from home in St. Lucia, to choose Majestic Views. 5 stars ⭐⭐⭐⭐⭐ (By the way, the view of the Pitons is exceptional). "
United States
Supriya
The price is £104
includes taxes & fees
6 Oct - 7 Oct
Majestic views of Pitons, Caribbean sea, amazing sunsets right from your room
A hand holding a drink with a straw and umbrella, by a swimming pool with clear blue water and a view of a bridge and greenery in the background.

20. La Heliconia

La Heliconia
3.0 star property
Calliste
8.0 out of 10, Very good, (467 reviews)
"The place was just perfect. Walking distance from the airport so ideal for solo Travellers and really safe. Rooms were great and pool was nice to chill in. Check in was smooth and straight forward. Host was very accommodating."
United States
Kerry
The price is £84
includes taxes & fees
11 Oct - 12 Oct
La Heliconia
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 Windward Islands Hotel Reviews

Bay Gardens Hotel

Bay Gardens Hotel

10/10 Excellent
"Great people with great customer service they go above and beyond to make sure your taken care of and all your needs are met"
Tyson 1-night trip
Posted 3 hours ago
Bay Gardens Hotel

Find out more about Windward Islands

Everything you need to know about Windward Islands holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windward Islands holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Windward Islands holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windward Islands holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windward Islands. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windward Islands holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windward Islands holiday rentals we have selected for you start as low as £53 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windward Islands rentals

At Expedia, we put the best Windward Islands holiday 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 Windward Islands 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 Windward Islands holiday.

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