A lush green landscape with a prominent mountain peak in the background and a body of water in the foreground.

Windward Islands Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Windward Islands vacation rentals

A kitchen with wooden cabinets, stainless steel appliances, a marble countertop, and a hanging chandelier.

1. Castle Berry Apartments

Brighton

Josel

CA $110 total

includes taxes & fees

Nov 15 - Nov 16

A balcony with a wicker tray holding a wine bottle, a glass, and fruits.

2. Seabliss Villa

Vieux Fort

"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."

Cassandra

CA $185 total

includes taxes & fees

Nov 11 - Nov 12

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

3. You 4 Ric Piton Suites

Soufriere

Stachio

CA $225 total

includes taxes & fees

Nov 23 - Nov 24

A wooden deck with wicker furniture, a pool, and a sign with porch rules.

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

Choiseul

Miss K.

CA $139 total

includes taxes & fees

Nov 11 - Nov 12

A poolside area with a lounge chair, a glass of drink, and a bottle of wine on a metal table.

5. Toraille Waterfall Villas

Soufriere

vanda

CA $221 total

includes taxes & fees

Nov 16 - Nov 17

A pool area with a view of the ocean and mountains, surrounded by greenery and a red-roofed building.

6. Samfi Gardens

Soufrière

Harinarayan

CA $223 total

includes taxes & fees

Nov 11 - Nov 12

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

Choiseul

Sherina

CA $344 total

includes taxes & fees

Nov 11 - Nov 12

A bed with white bedding, a brown pillow, and a small round tray with a red flower.

8. Agape Suites

Soufrière

Michael

CA $229 total

includes taxes & fees

Nov 11 - Nov 12

A modern hotel with a swimming pool, outdoor seating, and a multi-story building with balconies.

9. B&B HOME Fort de France Marina

Fort-de-France

Tabitha

CA $215 total

includes taxes & fees

Dec 2 - Dec 3

A balcony with curtains, a view of a lush landscape, and a building in the background.

10. Dalys Luxury Apartments

Choppins

Remy

CA $435 total

includes taxes & fees

Nov 18 - Nov 19

A modern kitchen with grey cabinets, a stainless steel refrigerator, a built-in oven, and a gas stove.

11. Condo in Gros Islet 10 Mins Drive to Beach

Gros Islet

Uniquea

CA $119 total

includes taxes & fees

Nov 19 - Nov 20

A swimming pool with a white balustrade, a covered outdoor seating area, and a white building with a red roof.

12. Cozy 1-Bdrm Studio in Rodney Bay with AC

Rodney Bay

Jaimie

CA $207 total

includes taxes & fees

Nov 12 - Nov 13

A swimming pool at sunset with a clear sky.

13. Hillview Apartments and Vehicle Rental

Grand Anse

Nerva

CA $109 total

includes taxes & fees

Dec 9 - Dec 10

A swimming pool surrounded by lush greenery and a view of a hilly landscape.

14. Vacation Club By Lush

Marigot Bay

Theresa Anne

CA $342 total

includes taxes & fees

Nov 12 - Nov 13

A compact kitchen with a dining area, a staircase, and a living room.

15. Caribbean Dream Vacation Property

Rodney Bay

Charmaine

CA $116 total

includes taxes & fees

Nov 18 - Nov 19

A neatly made bed with a white comforter and beige blankets, a large abstract painting above the bed, and a woven basket on the floor.

16. Appart'hôtel DLOKOKO

Le Bourg

Catherine

CA $304 total

includes taxes & fees

Nov 22 - Nov 23

A balcony with wicker furniture, a table, and potted plants.

17. Tropical apartment- Charming 1-bedroom apartment overlooking Soufriere town.

Soufriere

Rachel G.

CA $208 total

includes taxes & fees

Nov 25 - Nov 26

A wooden house with a porch, a dining area, and a kitchen visible through the open door.

18. Bogles Round House

Hillsborough

Harvey

CA $169 total

includes taxes & fees

Nov 15 - Nov 16

A tropical resort with a pool, palm trees, and a thatched-roof hut.

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

Castries

matthew p.

CA $144 total

includes taxes & fees

Nov 22 - Nov 23

A modern living room with a sofa, coffee table, and a TV mounted on the wall.

20. Vive mol

Rodney Bay

CA $204 total

includes taxes & fees

Nov 11 - Nov 12

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Find vacation rentals that suit your style

Top Windward Islands Hotel Reviews

A beach view with lounge chairs and a palm tree.

Silversands Beach House Adult only

Grand Anse

10/10 Excellent

Andrew

Samfi Gardens

Soufrière

10/10 Excellent

This was such an amazing property in soufriere! The staff were so sweet including their nighttime security guard Brian. The room was fully stocked and clean and beds super comfy. The view was spectacular and the pool had an amazing view as well. You can use the pool whenever you would like and the overall experience was outstanding. I would highly recommend this over the high end resorts for your overall budget and experience.

Ramanjoth

An aerial view of a coastal resort with clear turquoise waters, a sandy beach, and a pool area surrounded by palm trees.

Bequia Beach Hotel Luxury Resort & Spa

Bequia Island

10/10 Excellent

Beautiful property, beautiful gardens and beach, stunning scenery. A salt water pool and a freshwater pool, beach chairs and pristine beach. Great location for swimming in the sea as well. Delicious breakfast at the Bagatelle restaurant and great bar/lounge area! Every person working at the resort are friendly, welcoming, helpful and really just lovely. Management is amazing! Reception was outstanding as well - always a smile and so helpful. Our room was very well appointed and so comfortable...

Brenda

A modern kitchen with a stone accent wall, a large island with a sink, and a built-in oven.

Stonetrail

Villa

10/10 Excellent

I very much enjoyed staying here. It is still being built up . But That caused no issues for us . As with many parts of the Caribbean you do have some derelict buildings around . So it is not perfect , but it is perfect for me . The staff are fantastic . The units ( we were in a space for 2) are great . There was a resident cat that knew not to come in the apartment but was so happy to greet us . I'd stay here again .

RUNE

A hammock on a balcony with a view of the ocean and palm trees.

Petite Anse Hotel

St. Patrick

10/10 Excellent

We really enjoyed our stay at Petit Anse!!! We enjoyed all of our meals and drinks. We didn’t use the pool very much as we felt comfortable in the sea. The check-in was fast, efficient, and pleasant. Our cottage seemingly came with its own kitty cat. Tommy stayed with us for our entire stay which was by choice. Best outdoor cat ever! Thanks to all the staff - everyone was friendly!!! Thanks Chef for putting up with my food allergies and keeping me full and happy.

Steven J

A wooden deck with lounge chairs and a view of the sea.

BodyHoliday - All inclusive

Cap Estate

10/10 Excellent

Stephen

A balcony with a view of the ocean, a table with chairs, and a basket of fruit.

Villa Beach Cottages

Castries

10/10 Excellent

Could not have had a lovelier stay at Villa Beach Cottages- what a perfect home base for exploring the island! Check in was super quick and easy- i was offered a welcome drink and was in my room within minutes. Speaking of the room (21), my jaw hit the floor when i saw the view. It will literally take your breath away. Bedroom was large and spacious and tastefully furnished. The kitchen is fully equipped, should you wish to cook for yourself, but there are so many dining options in...

Brian

A beach with a lounge chair and a thatched umbrella.

Spice Island Beach Resort

Grand Anse

10/10 Excellent

Anonymous traveller

A modern hotel lobby with a pool view, wooden slats, and black wireframe chairs.

Silversands Grand Anse

Grand Anse

10/10 Excellent

Anonymous traveller

A balcony with a view of the sea, three sailboats, and outdoor seating.

Hotel Ti' Pelican

Saint-Pierre

10/10 Excellent

Un séjour de rêve! Superbe hôtel dans la plus belle ville de la Martinique, St-Pierre. L'hôtel est situé en bordure de la promenade piétonnière et de la mer. Un personnel des plus attachant et amical. Le propriétaire à pris le temps de passer en revue toutes les activités incontournables de l'île lors de notre arrivée. La ville est moins touristique qu'au sud mais nous avons été accueilli par les locaux avec gentillesse et bienveillance. Les amoureux de nature sauront apprécier les...

Rémi

A covered outdoor patio with a fountain, palm trees, and a view of the sea.

Grenadine House

Kingstown

10/10 Excellent

Kathy

A resort with a pool, lounge chairs, umbrellas, and a mountain view.

Sugar Beach, A Viceroy Resort

Soufrière

10/10 Excellent

they need to make aware to the guests that there is a dinner only on Tuesday nights on the Terrace. We were not informed of this nor was it advertised anywhere and we just stumbled on it after dinner that night. The entertainment needs to improve as well, as there should be something different every night. Also need a gift shop to purchase a few souvenirs that have Sugar Beach on it. As we were there just 2 weeks before Christmas, it would have been nice to at least have a Christmas tree near...

Don

A spa area with a hot tub, seating, and large windows offering a view of the sea.

Ti Kaye Resort & Spa - Adults Only

Canaries

10/10 Excellent

Stayed here on our honeymoon from Oct 15-19, 2017. Loved almost everything about Ti Kaye. Definitely secluded (1hr drive or more to any of the sights) but you could probably spend your entire trip on the resort if you aren't interested in traveling too far. Pros: Location, private beach, excellent staff, roomy cottages Cons: Food maybe a bit overpriced ( but comparable to the rest of St Lucia) and we weren't blown away by the dinners we had there, except: Don't miss: The Wednesday...

Trevor

A wooden pathway leading to a staircase surrounded by lush greenery and tropical plants.

Hotel French Coco

La Trinité

10/10 Excellent

Marie Soleil

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windward Islands vacation rentals we have selected for you start as low as CA $70 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 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.

Windward Islands Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windward Islands vacation rentals

1. Castle Berry Apartments

2. Seabliss Villa

3. You 4 Ric Piton Suites

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

5. Toraille Waterfall Villas

6. Samfi Gardens

7. the island experience samo

8. Agape Suites

9. B&B HOME Fort de France Marina

10. Dalys Luxury Apartments

11. Condo in Gros Islet 10 Mins Drive to Beach

12. Cozy 1-Bdrm Studio in Rodney Bay with AC

13. Hillview Apartments and Vehicle Rental

14. Vacation Club By Lush

15. Caribbean Dream Vacation Property

16. Appart'hôtel DLOKOKO

17. Tropical apartment- Charming 1-bedroom apartment overlooking Soufriere town.

18. Bogles Round House

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

20. Vive mol

Find vacation rentals that suit your style

Top Windward Islands Hotel Reviews

Silversands Beach House Adult only

10/10 Excellent

Find out more about Windward Islands

Windward Islands vacation rentals: An excellent choice for every season

How to find incredible deals on Windward Islands rentals