Windward Islands Vacation Rentals

Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Windward Islands vacation rentals

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
$117 nightly
The price is $123
Jun 17 - Jun 18
Total with taxes and fees
Hotel Panoramic
On the beach

Bogles Round House

Bogles Round House
2.5 star property
Hillsborough
8.8 out of 10, Excellent, (69 reviews)
"The attention to detail is incredible the outside kitchen was a blessing, the the restaurant is an architectural masterpiece, the food was delicious so delicious we had to meet the chef, all the staff were welcoming, attentive and personable. Roxanne has your every need in hand it was a pleasure to meet her. We will be back to stay in what I can only describe as a wellness retreat everything was just effortlessly perfect. "
United Kingdom
Lisa
$88 nightly
The price is $97
Jun 13 - Jun 14
Total with taxes and fees
Bogles Round House
Family Suite, Sea View | Dining

Appart'hôtel DLOKOKO

Appart'hôtel DLOKOKO
Le Bourg
$170 nightly
The price is $180
May 31 - Jun 1
Total with taxes and fees
Appart'hôtel DLOKOKO
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, (155 reviews)
"This experience was and will always be an enjoyable experience to remember. The host tried to speak English for us to help us understand. "
United States
Malaika
$143 nightly
The price is $149
May 28 - May 29
Total with taxes and fees
B&B HOME Fort de France Marina
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, (2 reviews)
"Great layout, large rooms, clean and appeared very new. I was concerned when no pictures of the inside in post, but it exceeded expectations. Nice quiet spot."
United States
Deborah
$113 nightly
The price is $133
Jun 18 - Jun 19
Total with taxes and fees
You 4 Ric Piton Suites
Desk, laptop workspace, iron/ironing board, free WiFi

Seaview Apartel

Seaview Apartel
2.5 star property
Castries
8.0 out of 10, Very Good, (36 reviews)
"Great location . Easy access to beach and market. Staff very helpful and kind."
United States
Navedita
$65 nightly
The price is $82
Jun 15 - Jun 16
Total with taxes and fees
Seaview Apartel
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.
$104 nightly
The price is $112
May 26 - May 27
Total with taxes and fees
Anne's Home Away from Home
Fountain

Village Creole

Village Creole
3.0 star property
Pointe du Bout
8.2 out of 10, Very Good, (135 reviews)
"The apartment is very much worn out, pretty different than what it looks like in the pics. Convenient location, nice check in/check out staff."
Italy
Chiara
$89 nightly
The price is $94
May 31 - Jun 1
Total with taxes and fees
Village Creole
Superior Apartment | Terrace/patio

Kaouanne

Kaouanne
Pointe du Bout
9.2 out of 10, Wonderful, (106 reviews)
"very good location. studio was very spatious and clean. excellent value"
Canada
AURELIEN
$123 nightly
The price is $132
Jun 24 - Jun 25
Total with taxes and fees
Kaouanne
Terrace/patio

Sadewa Villa

Sadewa Villa
4.5 star property
Bequia Island
9.6 out of 10, Exceptional, (7 reviews)
"Very unique house with great views. The property could use some repairs and maintenance, but overall a good experience. "
United States
Jeffrey
$268 nightly
The price is $300
May 26 - May 27
Total with taxes and fees
Sadewa Villa
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
Jun 1 - Jun 2
Total with taxes and fees
Seabliss Villa
Beach nearby, white sand, 4 beach bars

Hillview Apartments and Vehicle Rental

Hillview Apartments and Vehicle Rental
3.0 star property
Grand Anse
8.2 out of 10, Very Good, (128 reviews)
"My go too … place to stay every time I’m in Grenada… always very accommodating to my needs .. great pool with a view that’s breathtaking… recommend this place to anyone who wants a at home feel!!!"
United States
Tessa
$49 nightly
The price is $55
Jun 1 - Jun 2
Total with taxes and fees
Hillview Apartments and Vehicle Rental
Exterior

Sy Villa

Sy Villa
3.0 star property
Choiseul
$130 nightly
The price is $151
Jun 5 - Jun 6
Total with taxes and fees
Sy Villa
Beach/ocean view

Le Paradis de l'Anse

Le Paradis de l'Anse
Riviere-Pilote
8.2 out of 10, Very Good, (452 reviews)
"Reception and restaurant on site are often closed which is very deceiving. The beach is not very long and full of plaque of thick rocks."
Canada
Anick
$84 nightly
The price is $89
Jun 2 - Jun 3
Total with taxes and fees
Le Paradis de l'Anse
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
$110 nightly
The price is $131
May 30 - May 31
Total with taxes and fees
Union Hilltop Paradise Villas
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
$95 nightly
The price is $104
May 29 - May 30
Total with taxes and fees
Cabier Ocean Lodge
Villa | Private kitchen | Fridge, microwave, oven, stovetop

Story Villa, 1 Bedroom With Ocean & Mountain View

Story Villa, 1 Bedroom With Ocean & Mountain View
3.0 star property
Canaries
10.0 out of 10, Exceptional, (1 review)
"Villa as described, though there was one thing that was not and we let the owner know. "
United States
Diana
$120 nightly
The price is $120
May 26 - May 27
Total with taxes and fees
Story Villa, 1 Bedroom With Ocean & Mountain View
Outdoor pool, pool umbrellas, sun loungers

Redoute Paradise

Redoute Paradise
Fort-de-France
9.6 out of 10, Exceptional, (48 reviews)
"Excellent service, kind and courteous staff and nice ambiance. Breakfast was amazing."
United States
aneesa
$191 nightly
The price is $196
May 27 - May 28
Total with taxes and fees
Redoute Paradise
Beach nearby, white sand

ClarenceVille Villa Apartments

ClarenceVille Villa Apartments
3.5 star property
St. David
7.6 out of 10, Good, (9 reviews)
"The lady at the property was great an happy birthday to her in advance 80yrs🙏"
United States
Arthur
$297 nightly
The price is $306
May 26 - May 27
Total with taxes and fees
ClarenceVille Villa Apartments
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
$211 nightly
The price is $238
May 26 - May 27
Total with taxes and fees
the island experience samo
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

Royalton Hideaway Saint Lucia, An Autograph Collection All-Inclusive Resort - Adults Only

Royalton Hideaway Saint Lucia, An Autograph Collection All-Inclusive Resort - Adults Only

10/10 Excellent
"Managment of Royalton was great . very professional especially “ Gabriel “ and “Mervin “ they were always ready to provide world class customer service and going above and beyond to make sure their guests are taking care of . But unfortunately the front desk staff in Hideaway lobby wasn’t very helpful and available to address the issues. I called at 6:30 am to arrange for the bellboy to pick my my luggage at 7:00 am from my room for checking out and catching my shuttle to airport the front desk of Royalton confirmed bellboy will be there to help me but until 7:10 am nobody showed up and nobody contacted me about the delay I had to carry all my suitcases by myself to the Hideaway lobby even I had injury as I didn’t want to lose my transportation to airport due to unorganized front desk staff and their delay. I suggest the management should periodically get feedback from the guests when they are on site in hotel to find out about their STAFF /employee behaviour and their customer service SKILLS . I have to thank “ Tashael “the Expedia representative for her support and excellent customer service. She was amazing. Overall Hotel was very clean and beautiful, senior management was excellent and professional and always ready to assist the guests but unfortunately regular staff didn’t provide proper customer service to the guests."
SHAHLA 9-night trip
Posted 2 hours ago
Royalton Hideaway Saint Lucia, An Autograph Collection All-Inclusive Resort - Adults Only

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 $55 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.