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

Windward Islands Vacation Rentals

Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Windward Islands vacation rentals

Outdoor dining

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.
$105 nightly
The price is $111
Jul 19 - Jul 20
Total with taxes and fees
Anne's Home Away from Home
Apartment, Terrace, Partial Sea View | Living area | 43-inch flat-screen TV with digital channels, Smart TV, Netflix

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
$113 nightly
The price is $133
Aug 13 - Aug 14
Total with taxes and fees
You 4 Ric Piton Suites
Terrace/patio

Seabliss Villa

Seabliss Villa
3.0 star property
Vieux Fort
7.2 out of 10, Good, (5 reviews)
"This place was amazing. Everyone is so nice and very helpful. We didn't know anything in the area and they all was kind enough to tell us different places to visit and see. I recommend this place to everyone. Thank you"
United States
Dincer
$125 nightly
The price is $146
Aug 1 - Aug 2
Total with taxes and fees
Seabliss Villa
On the beach

Bogles Round House

Bogles Round House
2.5 star property
Hillsborough
8.8 out of 10, Excellent, (71 reviews)
"I stay at the Round House whenever I visit Carriacou. I was happy to hear that the Hotel was not too badly damaged after the 2024 hurricane and as usual, had a very enjoyable stay."
United States
Jonathan
$109 nightly
The price is $120
Jul 21 - Jul 22
Total with taxes and fees
Bogles Round House
Family Suite, Sea View | Dining

Appart'hôtel DLOKOKO

Appart'hôtel DLOKOKO
Le Bourg
$219 nightly
The price is $230
Jul 19 - Jul 20
Total with taxes and fees
Appart'hôtel DLOKOKO
Fountain

Village Creole

Village Creole
3.0 star property
Pointe du Bout
8.2 out of 10, Very Good, (139 reviews)
"Great location"
Canada
Abdoul Razack Farid
$91 nightly
The price is $96
Jul 21 - Jul 22
Total with taxes and fees
Village Creole
Terrace/patio

The Island Experience- Melo Newly Listed!!!

The Island Experience- Melo Newly Listed!!!
Choiseul
9.0 out of 10, Wonderful, (32 reviews)
"Good value"
United States
Shannon S.
$107 nightly
The price is $107
Jul 20 - Jul 21
Total with taxes and fees
The Island Experience- Melo Newly Listed!!!
Exterior

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.
$108 nightly
The price is $108
Jul 19 - Jul 20
Total with taxes and fees
La Bwizan Inn -Apartment #2-
Exterior

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
$70 nightly
The price is $70
Jul 26 - Jul 27
Total with taxes and fees
Comfort Suites- Special
Living area

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
$195 nightly
The price is $223
Jul 23 - Jul 24
Total with taxes and fees
the island experience samo
Exterior

Sy Villa

Sy Villa
3.0 star property
Choiseul
$115 nightly
The price is $135
Jul 23 - Jul 24
Total with taxes and fees
Sy Villa
Terrace/patio

The Island Experiences-Samo

The Island Experiences-Samo
Choiseul
8.6 out of 10, Excellent, (19 reviews)
"It was a lovely tropical paradise, yet felt grounded and one with the neighborhood. "
United Kingdom
Frederic W.
$102 nightly
The price is $106
Jul 27 - Jul 28
Total with taxes and fees
The Island Experiences-Samo
Luxury Apartment, 1 Bedroom, Balcony | Balcony

Calliandras Apartment Complex

Calliandras Apartment Complex
3.5 star property
Ratho Mill
7.4 out of 10, Good, (12 reviews)
"The room was very clean and comfortable. Easy to contact staff for directions, extra services etc. Excellent customer service "
United States
Valissa
$90 nightly
The price is $102
Jul 27 - Jul 28
Total with taxes and fees
Calliandras Apartment Complex
Outdoor pool, sun loungers

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, (160 reviews)
"Excellent stay ! Pool Is great! Have some spots around the corner about 7 minutes walk. good communication Highly recommended"
United States
Kaisher
$155 nightly
The price is $161
Jul 19 - Jul 20
Total with taxes and fees
B&B HOME Fort de France Marina
Superior Apartment | Private kitchen | Coffee/tea maker, fridge, microwave, oven

Tranquility Suites- Feels like home

Tranquility Suites- Feels like home
3.5 star property
Choiseul
8.6 out of 10, Excellent, (21 reviews)
"Great stay and definitely recommended."
United States
Ying
$132 nightly
The price is $152
Aug 8 - Aug 9
Total with taxes and fees
Tranquility Suites- Feels like home
Outdoor pool

Hotel Panoramic

Hotel Panoramic
3.0 star property
Trois-Ilets
8.6 out of 10, Excellent, (326 reviews)
"Very near beach and small town. Convenient location to beach hop each day in our rental car. "
Canada
Hektor
$133 nightly
The price is $139
Jul 26 - Jul 27
Total with taxes and fees
Hotel Panoramic
Desk, laptop workspace, iron/ironing board, WiFi (free)

Seaview Apartel

Seaview Apartel
2.5 star property
Castries
8.0 out of 10, Very Good, (38 reviews)
"The close proximity to the city"
United States
Carla
$60 nightly
The price is $76
Jul 23 - Jul 24
Total with taxes and fees
Seaview Apartel
Front of property

Daze Off

Daze Off
3.5 star property
Vieux Fort
9.8 out of 10, Exceptional, (17 reviews)
"The property was very well kept. And the host was amazing."
United States
Mary
$200 nightly
The price is $225
Jul 19 - Jul 20
Total with taxes and fees
Daze Off
Standard Room, 1 Queen Bed, Balcony, Beach View | Beach/ocean view

Cabier Ocean Lodge

Cabier Ocean Lodge
3.0 star property
St. Andrew
8.8 out of 10, Excellent, (66 reviews)
"Lovely quiet retreat. Great food and wonderful staff."
United Kingdom
mark
$100 nightly
The price is $110
Jul 19 - Jul 20
Total with taxes and fees
Cabier Ocean Lodge
Exterior

Union Hilltop Paradise Villas

Union Hilltop Paradise Villas
3.5 star property
Castries
9.0 out of 10, Wonderful, (2 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
$116 nightly
The price is $136
Jul 23 - Jul 24
Total with taxes and fees
Union Hilltop Paradise Villas
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

Zoetry Marigot Bay - All Inclusive

Zoetry Marigot Bay - All Inclusive

10/10 Excellent
"Whenever you see the big boss come and help you to your table or come to the table to ask if everything is ok. Ask how they can improve is a HUGE plus. It says a lot. You see the big boys walking throughout the property is as impressive as can say enough."
Rosine 6-night trip
Posted 15 hours ago
Zoetry Marigot Bay - All Inclusive

Find out more about Windward Islands

Everything you need to know about Windward Islands 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 Windward Islands 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 Windward Islands vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windward Islands vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windward Islands 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 $75 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 Windward Islands rentals

At Expedia, we put the best Windward Islands 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 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 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 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.