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

Windward Islands Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Windward Islands vacation rentals

Outdoor pool, sun loungers

1. 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, (166 reviews)
"We loved everything."
United Kingdom
Tabitha
$134 nightly
The price is $140
Sep 6 - Sep 7
Total with taxes and fees
B&B HOME Fort de France Marina
Fountain

2. Village Creole

Village Creole
3.0 star property
Pointe du Bout
8.2 out of 10, Very Good, (143 reviews)
"Great location"
Canada
Abdoul Razack Farid
$100 nightly
The price is $105
Sep 10 - Sep 11
Total with taxes and fees
Village Creole
On the beach

3. 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
$109 nightly
The price is $120
Sep 7 - Sep 8
Total with taxes and fees
Bogles Round House
Apartment, Terrace, Partial Sea View | Living area | 43-inch flat-screen TV with digital channels, Smart TV, Netflix

4. 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
$117 nightly
The price is $137
Sep 13 - Sep 14
Total with taxes and fees
You 4 Ric Piton Suites
Standard Room, Hill View (Escape) | Terrace/patio

5. Samfi Gardens

Samfi Gardens
2.5 star property
Soufrière
9.8 out of 10, Exceptional, (217 reviews)
"This place was absolutely perfect! The location is amazing. The staff are all super friendly, helpful, and greet you with a smile every time they see you. The rooms are well-kept and have a great kitchenette that is fully stocked. I look forward to returning to the island, and when we do, this will be the only place we stay."
United States
Timothy
$176 nightly
The price is $187
Sep 18 - Sep 19
Total with taxes and fees
Samfi Gardens
Superior Apartment | Terrace/patio

6. Kaouanne

Kaouanne
Pointe du Bout
9.2 out of 10, Wonderful, (112 reviews)
"Quiet, peaceful, nice view, good location, helpful staff, good kitchen"
United States
Willie
$120 nightly
The price is $130
Oct 5 - Oct 6
Total with taxes and fees
Kaouanne
Family Suite, Sea View | Dining

7. Appart'hôtel DLOKOKO

Appart'hôtel DLOKOKO
Le Bourg
9.0 out of 10, Wonderful, (2 reviews)
"L’appartement est beau, propre et actuel! Toutes les commodités y sont ! L’emplacement est très bien! La salle de bain est petite, mais c’est correct. Nous avons beaucoup aimé !"
Canada
Catherine
$141 nightly
The price is $147
Sep 27 - Sep 28
Total with taxes and fees
Appart'hôtel DLOKOKO
Outdoor pool, sun loungers

8. La Heliconia

La Heliconia
3.0 star property
Calliste
8.0 out of 10, Very Good, (463 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
$94 nightly
The price is $104
Sep 11 - Sep 12
Total with taxes and fees
La Heliconia
Comfort Apartment, Garden View | 1 bedroom, in-room safe, iron/ironing board, rollaway beds (free)

9. Vee's Country Apartments

Vee's Country Apartments
3.5 star property
Micoud
8.4 out of 10, Very Good, (6 reviews)
"the pictures don’t do it justice with how beautiful this stay is !!! 1000/10, i would definitely re book again"
Canada
Chanelle
$63 nightly
The price is $80
Sep 25 - Sep 26
Total with taxes and fees
Vee's Country Apartments
Terrace/patio

10. 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
$129 nightly
The price is $150
Sep 11 - Sep 12
Total with taxes and fees
Seabliss Villa
Beach nearby, white sand, 4 beach bars

11. Hillview Apartments and Vehicle Rental

Hillview Apartments and Vehicle Rental
3.0 star property
Grand Anse
8.2 out of 10, Very Good, (147 reviews)
"Very accommodating host"
United States
Wendon
$60 nightly
The price is $67
Oct 6 - Oct 7
Total with taxes and fees
Hillview Apartments and Vehicle Rental
Desk, laptop workspace, iron/ironing board, WiFi (free)

12. Seaview Apartel

Seaview Apartel
2.5 star property
Castries
8.0 out of 10, Very Good, (44 reviews)
"Property was very good and accomendating. Really hope to come back sooner, its very close to main city."
United States
Stefan Winston Lamar
$65 nightly
The price is $82
Sep 6 - Sep 7
Total with taxes and fees
Seaview Apartel
Living area

13. 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
$217 nightly
The price is $244
Sep 6 - Sep 7
Total with taxes and fees
the island experience samo
Superior Apartment | Private kitchen | Coffee/tea maker, fridge, microwave, oven

14. 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
Sep 7 - Sep 8
Total with taxes and fees
Tranquility Suites- Feels like home
Villa | Living area

15. WindBlow Villa

WindBlow Villa
3.0 star property
Belmont
3.0 out of 10, (2 reviews)
"My stay at windblow was very disappointing. I was booked from Feb 22 to 3/1 and left on Feb 23. The studio apartment had no draws, no nightstand, the sink in the bathroom was so tiny we ended up washing our faces in the kitchen sink because we would bump our heads trying to use bathroom sink. The Villa advertised as “quiet time” at night but had a dog that wasn’t disclosed,on site that howled for long periods of time.The shower caddy was so nasty it looked like something was growing out of it...
United States
Lisa
$91 nightly
The price is $103
Sep 12 - Sep 13
Total with taxes and fees
WindBlow Villa
Apartment, Mountain View | Balcony view

16. Agape Suites

Agape Suites
3.0 star property
Soufrière
10.0 out of 10, Exceptional, (18 reviews)
"It was like home away from home "
United States
Karl
$124 nightly
The price is $145
Oct 6 - Oct 7
Total with taxes and fees
Agape Suites
Standard Room, 1 Queen Bed, Balcony, Beach View | Beach/ocean view

17. Cabier Ocean Lodge

Cabier Ocean Lodge
3.0 star property
St. Andrew
8.8 out of 10, Excellent, (69 reviews)
"Lovely quiet retreat. Great food and wonderful staff."
United Kingdom
mark
$94 nightly
The price is $104
Sep 6 - Sep 7
Total with taxes and fees
Cabier Ocean Lodge
Front of property

18. Daze Off

Daze Off
3.5 star property
Vieux Fort
10.0 out of 10, Exceptional, (21 reviews)
"This was a wonderful property with a modern design and attention to detail. It was very convenient by car to the local restaurants. While minimalist , it offered everything we needed."
United States
Ian
$257 nightly
The price is $286
Sep 6 - Sep 7
Total with taxes and fees
Daze Off
Exterior

19. Union Hilltop Paradise Villas

Union Hilltop Paradise Villas
3.5 star property
Castries
9.0 out of 10, Wonderful, (4 reviews)
"This place was great, I almost didn't want to leave a good review because I want to keep this gem to myself! The staff was friendly and very personable. The property also isnt too far from anything. I had one small issue with my room and it was rectified within minutes. All in all I had a great stay."
United States
Danique
$118 nightly
The price is $138
Sep 6 - Sep 7
Total with taxes and fees
Union Hilltop Paradise Villas
Villa | Private kitchen | Fridge, microwave, oven, stovetop

20. 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
$115 nightly
The price is $115
Sep 11 - Sep 12
Total with taxes and fees
Story Villa, 1 Bedroom With Ocean & Mountain View
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windward Islands Hotel Reviews

Radisson Grenada Beach Resort

Radisson Grenada Beach Resort

8/10 Good
"I really enjoyed my stay at the Radisson Hotel. The staff were friendly and helpful, the room was clean and comfortable, and the overall atmosphere was great. The location was also convenient, and I had a pleasant experience overall. My only issue was the Wi-Fi. The connection in my room was quite poor and kept dropping, which was frustrating, especially when I needed to use the internet. Hopefully, this can be improved. Aside from the Wi-Fi issue, I had a great stay and would definitely consider staying here again."
Janelle 3-night trip
Posted 7 hours ago
Radisson Grenada Beach Resort

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 $67 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.