Holiday Rentals Windward Islands from ฿2,512: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Windward Islands holiday rentals

A hand holding a drink with a straw and umbrella, by a swimming pool with clear blue water and a view of a bridge and greenery in the background.

1. La Heliconia

Calliste

Kerry

฿4,022 total

includes taxes & fees

29 Sept - 30 Sept

A kitchen with a view of the ocean and palm trees.

2. Appart'hôtel DLOKOKO

Le Bourg

Catherine

฿5,065 total

includes taxes & fees

29 Sept - 30 Sept

A wooden deck with a white railing overlooking a beach with clear blue water and a rocky outcrop in the distance.

3. Cabier Ocean Lodge

St. Andrew

mark

฿4,207 total

includes taxes & fees

29 Sept - 30 Sept

A beach with clear blue water, sandy shore, and dense green foliage.

4. Bogles Round House

Hillsborough

Harvey

฿4,006 total

includes taxes & fees

11 Oct - 12 Oct

A view of a coastal town with palm trees and mountains in the background.

5. Samfi Gardens

Soufrière

Timothy

฿6,641 total

includes taxes & fees

29 Sept - 30 Sept

A neatly made bed with a folded towel and a decorative swan towel on a dark blue blanket.

6. Seaview Apartel

Castries

Stefan Winston Lamar

฿3,027 total

includes taxes & fees

29 Sept - 30 Sept

A swimming pool with lounge chairs and a thatched umbrella, surrounded by tropical plants and a clear sky.

7. Hotel Panoramic

Trois-Ilets

Hektor

฿4,881 total

includes taxes & fees

12 Oct - 13 Oct

A pink building with arched windows and a staircase leading to the entrance.

8. Beachcross Villa Apartments

Rodney Bay

Cherise

฿4,219 total

includes taxes & fees

1 Oct - 2 Oct

A beach with a wooden pier extending into the water, lined with beach umbrellas and people relaxing.

9. Hillview Apartments and Vehicle Rental

Grand Anse

Wendon

฿2,512 total

includes taxes & fees

27 Oct - 28 Oct

A modern kitchen with white cabinets, a stainless steel refrigerator, two bar stools, and pendant lights.

10. Tranquility Suites- Feels like home

Choiseul

Ying

฿5,075 total

includes taxes & fees

30 Sept - 1 Oct

A coastal scene with clear water, boats, and a tree with green leaves.

11. Mandela Court Grenada

Lance aux Épines

Janell

฿7,888 total

includes taxes & fees

29 Sept - 30 Sept

An outdoor dining area with a long table set for a formal event, surrounded by lush greenery.

12. Caribbean Dream Vacation Property

Rodney Bay

Charmaine

฿3,261 total

includes taxes & fees

6 Oct - 7 Oct

A beach scene with palm trees, a boat, and a sunset.

13. L'Impératrice Village Résidence Hôtelière

Trois-Ilets

suelyn

฿3,073 total

includes taxes & fees

29 Sept - 30 Sept

A coastal area with a marina, boats, and a beach with palm trees.

14. Vacation Club By Lush

Marigot Bay

Stuart

฿7,605 total

includes taxes & fees

29 Sept - 30 Sept

15. 1-Bdrm Studio Retreat in Rodney Bay w AC

Rodney Bay

฿4,902 total

includes taxes & fees

29 Sept - 30 Sept

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

Rodney Bay

Lester

฿4,002 total

includes taxes & fees

29 Sept - 30 Sept

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

17. Wave Crest Suites

Grand Anse

Ashley

฿2,644 total

includes taxes & fees

29 Sept - 30 Sept

A bed with white pillows and a textured white bedspread.

18. Vee's Country Apartments

Micoud

Chanelle

฿2,973 total

includes taxes & fees

29 Sept - 30 Sept

A spacious indoor area with a seating arrangement, a vehicle, and a reception desk.

19. Vigie Beach Suite 1

Vigie

฿5,706 total

includes taxes & fees

29 Sept - 30 Sept

A balcony with a table set for breakfast, overlooking a coastal view.

20. Kaouanne

Pointe du Bout

Willie

฿4,746 total

includes taxes & fees

29 Oct - 30 Oct

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Top Windward Islands Hotel Reviews

Royalton Grenada, An Autograph Collection All-Inclusive Resort

10/10 Excellent

"Staff was excellent."

Bel Jou Hotel – Adults Only – All Inclusive

10/10 Excellent

"Huge shoutout to the incredible staff at Bel Jou—Dana ( my name sake)Jemima, Brendan, Princess, the chefs, and everyone else who made my stay world-class! The hospitality is impeccable, and as a Bajan living in the US, I was so proud to experience that signature Caribbean warmth. The property is impeccably maintained, and I especially appreciated the top-notch security, including their attentive check-outs when I left in a private taxi. From taking advantage of all the amenities to using the Bel Jou taxi shuttle, everything was seamless. Great views, great people, and great vibes—I couldn't have asked for a better stay"

Radisson Grenada Beach Resort

10/10 Excellent

"I had a pleasant stay at the Radisson Grenada Beach Resort. The staff were very friendly, welcoming, and helpful, which really made the experience enjoyable. The location is beautiful, and the overall atmosphere was relaxing. One small issue I noticed was with the complimentary water in the room. There were three guests staying in the room, but only two complimentary bottles of water were provided. It would have been nice to have one bottle per guest, especially since the room was booked for three people. Overall, I enjoyed my stay and appreciated the friendly service. With a few small improvements to the room amenities, the experience could be even better"

Zoetry Marigot Bay - All Inclusive

8/10 Good

"Overall, we enjoyed our stay at Zoëtry. However, the stairs were difficult to navigate. I generally had a positive experience with the staff, except on our final day when the resort lost power. We requested assistance with our luggage but ultimately had to struggle carrying it down the stairs and up to the lobby. I understand that the staff had no control over the power outage, but the situation should have been handled differently. If the resort has experienced outages before, there should be a backup plan to assist guests who are checking out, especially since most travelers have tight schedules and need to get to the airport. It was especially disappointing to feel as though the staff ignored us while we were visibly struggling. My advice to management is to develop and implement a clear plan for assisting guests during power outages. We paid the same rate as every other guest and should not have been overlooked. Unfortunately, this experience cast a dark cloud over what was otherwise an enjoyable vacation."

Ti Kaye Resort & Spa - Adults Only

10/10 Excellent

"This place was a dream.... If you're looking for relaxation this was a wonderful option. The views are perfect. The rooms and facilities were always clean. The staff we're always friendly and accommodating. The spa and staff there were wonderful. Breakfast was great, but dinner was a bit salty once or twice, but they had options that was great. Also, Their beach is way better than sugar beach in my opinion."

Find out more about Windward Islands

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windward Islands holiday rentals

1. La Heliconia

2. Appart'hôtel DLOKOKO

3. Cabier Ocean Lodge

4. Bogles Round House

5. Samfi Gardens

6. Seaview Apartel

7. Hotel Panoramic

8. Beachcross Villa Apartments

9. Hillview Apartments and Vehicle Rental

10. Tranquility Suites- Feels like home

11. Mandela Court Grenada

12. Caribbean Dream Vacation Property

13. L'Impératrice Village Résidence Hôtelière

14. Vacation Club By Lush

15. 1-Bdrm Studio Retreat in Rodney Bay w AC

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

17. Wave Crest Suites

18. Vee's Country Apartments

19. Vigie Beach Suite 1

20. Kaouanne

Find holiday rentals that suit your style

Top Windward Islands Hotel Reviews

Royalton Grenada, An Autograph Collection All-Inclusive Resort

Bel Jou Hotel – Adults Only – All Inclusive

Windjammer Landing Resort and Residences

Bay Gardens Hotel

Radisson Grenada Beach Resort

Zoetry Marigot Bay - All Inclusive

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

Ti Kaye Resort & Spa - Adults Only

Jade Mountain Resort

Find out more about Windward Islands

Go further with the Expedia app

Search Holiday Rentals in Windward Islands

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windward Islands holiday rentals

1. La Heliconia

2. Appart'hôtel DLOKOKO

3. Cabier Ocean Lodge

4. Bogles Round House

5. Samfi Gardens

6. Seaview Apartel

7. Hotel Panoramic

8. Beachcross Villa Apartments

9. Hillview Apartments and Vehicle Rental

10. Tranquility Suites- Feels like home

11. Mandela Court Grenada

12. Caribbean Dream Vacation Property

13. L'Impératrice Village Résidence Hôtelière

14. Vacation Club By Lush

15. 1-Bdrm Studio Retreat in Rodney Bay w AC

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

17. Wave Crest Suites

18. Vee's Country Apartments

19. Vigie Beach Suite 1

20. Kaouanne

Find holiday rentals that suit your style

Top Windward Islands Hotel Reviews

Royalton Grenada, An Autograph Collection All-Inclusive Resort

Find out more about Windward Islands

Go further with the Expedia app