Windward Islands Vacation Rentals from $77: Search Short-Term Rentals

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In two weeks

Nov 6 - Nov 8

In two months

Dec 18 - Dec 20

In three months

Jan 15 - Jan 17

In four months

Feb 12 - Feb 14

Our top choices for Windward Islands vacation rentals

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

1. Agape Suites

Soufrière

Michael

$100 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

2. Bogles Round House

Hillsborough

Harvey

$109 nightly

Oct 28 - Oct 29

Total with taxes and fees

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

3. Toraille Waterfall Villas

Soufriere

vanda

$133 nightly

Nov 25 - Nov 26

Total with taxes and fees

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

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

Castries

matthew p.

$110 nightly

Oct 26 - Oct 27

Total with taxes and fees

A swimming pool with a tiled edge, surrounded by a red fence and potted plants.

5. Comfort Suites- Special

Choiseul

HALEY

$70 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

6. 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

$131 nightly

Oct 29 - Oct 30

Total with taxes and fees

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

7. You 4 Ric Piton Suites

Soufriere

Stachio

$123 nightly

Nov 2 - Nov 3

Total with taxes and fees

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

8. Samfi Gardens

Soufrière

Harinarayan

$139 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

9. Caribbean Dream Vacation Property

Rodney Bay

Charmaine

$65 nightly

Nov 25 - Nov 26

Total with taxes and fees

A multi-story building with a blue exterior, a staircase leading to the upper floors, and a garage door.

10. La Bwizan Inn -Apartment #2-

Laborie

Christina R.

$108 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

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

Choiseul

Miss K.

$107 nightly

Oct 26 - Oct 27

Total with taxes and fees

A wooden deck with lounge chairs, a small table, and a hammock.

12. The Island Experiences-Samo

Choiseul

Ashley s.

$102 nightly

Oct 26 - Oct 27

Total with taxes and fees

A wooden table with a woven ball, a vase with dried plants, and a pair of rings.

13. Seaview Apartel

Castries

Desmond

$65 nightly

Nov 10 - Nov 11

Total with taxes and fees

A swimming pool with a clear blue water surface, surrounded by lush greenery and a covered area with white canopies.

14. Redoute Paradise

Fort-de-France

aneesa

$157 nightly

Oct 26 - Oct 27

Total with taxes and fees

A modern living room with a white sofa, a dining table with chairs, and a kitchen area with a stove, microwave, and refrigerator.

15. the island experience samo

Choiseul

Sherina

$217 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

16. B&B HOME Fort de France Marina

Fort-de-France

Tabitha

$151 nightly

Oct 26 - Oct 27

Total with taxes and fees

A balcony with a view of the ocean and lush greenery.

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

Choiseul

"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). "

Supriya

$134 nightly

Oct 26 - Oct 27

Total with taxes and fees

A bedroom with two beds, a small bedside table, a nightstand, a window with curtains, a door leading to a bathroom, and a geometric rug.

18. Vee's Country Apartments

Micoud

Chanelle

$62 nightly

Oct 27 - Oct 28

Total with taxes and fees

A covered balcony with two white wicker chairs, a tiled floor, and a view of a hillside with buildings.

19. Wave Crest Suites

Grand Anse

Edlyn

$81 nightly

Oct 26 - Oct 27

Total with taxes and fees

A living room with a beige sofa, a TV on a wooden table, and a balcony with a white railing and potted plants.

20. Sandrati Villa

Bequia Island

Brandon

$146 nightly

Oct 29 - Oct 30

Total with taxes and fees

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Top Windward Islands Hotel Reviews

Coconut Bay Beach Resort & Spa All Inclusive

10/10 Excellent

"This place was amazing from the room to the staff and also the food. Want to give a big shoutout to Dillian and Dre at the harmony pool bar"

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

10/10 Excellent

"From the view to the cleanliness to the fun things you can do on the resort, it was all an AMAZING experience 🔥 All the staff was just so nice & everyone seemed happy . Will definitely come back"

True Blue Bay Resort

10/10 Excellent

"We had a great honeymoon they decorated our room for us with Swan towels and flower petals the dodgy dock restaurant was good staff was very nice the beach shuttle at 9am and 12pm was very easy to get to grand anse beach and the umbrella restaurant there was great they make their own ice cream at the resort and have yoga classes"

Royalton Grenada, An Autograph Collection All-Inclusive Resort

8/10 Good

"Beach is beautiful and staff are friendly and helpful. They went out of their way to make accommodations for a friend with disabilities. I was really impressed! The door on the balcony did not lock but I did feel safe as I was on the 3rd floor. One day I put the sign out to have my room cleaned and it was mistaken for a do not disburse sign. If you want service, don't put up a sign. Lots of food options."

Windjammer Landing Resort and Residences

10/10 Excellent

"My husband and I celebrated our 14th wedding anniversary at Windjammer Landing in Saint Lucia, and our stay was beautiful! Our two-bedroom, three-bathroom villa with a private infinity pool was a highlight. The views were breathtaking, and we loved having space to relax and enjoy time together. The beach was gorgeous, with clear water and little fish swimming around us. We also enjoyed a couples massage, which added to the relaxation. Between the villa, the views, and the beach, we had so many moments where we simply stopped and appreciated being there. Windjammer Landing was a beautiful setting for our anniversary and gave us memories we’ll treasure. ❤️"

Ladera Resort - Adults Only

10/10 Excellent

"We had a great stay at Ladera! The view is everything you can imagine and more. The staff was so respectful, kind and on top of everything you need. We didn’t wait more than 5-10 minutes when we called for anything. There were some small complaints but Yvette and her staff went above and beyond to ensure they were resolved… even upgraded our room! The resort tries their best to manage bugs by spraying nightly and as needed but of course, you are in nature so be aware bugs are still in abundance but only at night time. The hotel set us up with any excursions we wanted to do and the food at Dasheene was amazing. Overall, it was a great stay & would definitely recommend."

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 $77 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.

Room 1

Check prices for these dates

Our top choices for Windward Islands vacation rentals

1. Agape Suites

2. Bogles Round House

3. Toraille Waterfall Villas

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

5. Comfort Suites- Special

6. Seabliss Villa

7. You 4 Ric Piton Suites

8. Samfi Gardens

9. Caribbean Dream Vacation Property

10. La Bwizan Inn -Apartment #2-

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

12. The Island Experiences-Samo

13. Seaview Apartel

14. Redoute Paradise

15. the island experience samo

16. B&B HOME Fort de France Marina

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

18. Vee's Country Apartments

19. Wave Crest Suites

20. Sandrati Villa

Find vacation rentals that suit your style

Top Windward Islands Hotel Reviews

Coconut Bay Beach Resort & Spa All Inclusive

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

True Blue Bay Resort

Royalton Grenada, An Autograph Collection All-Inclusive Resort

Harbor Club St. Lucia, Curio Collection by Hilton

Ti Kaye Resort & Spa - Adults Only

Windjammer Landing Resort and Residences

Rabot Hotel from Hotel Chocolat

Ladera Resort - Adults Only

Find out more about Windward Islands