A coastal town with colorful buildings, a marina with boats, and a mountainous backdrop.

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Check prices for these dates

This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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Our top choices for Leeward hotels

A beach resort with lounge chairs, a gazebo, and a mountain in the background.

1. Le Sereno

Le Sereno
5.0 star property
Grand Cul-de-Sac
9.6 out of 10, Exceptional, (62 reviews)
"Loved our time at this property! The staff was really warm and the location is so unique! "
United States
babi
Le Sereno
A resort pool area with a curved design, lounge chairs, umbrellas, and a building with a light-colored facade.

2. Oyster Bay Beach Resort

Oyster Bay Beach Resort
4.0 star property
Oyster Pond
9.0 out of 10, Wonderful, (1,001 reviews)
"Great place to stay"
United States
Marv
The price is S$270
includes taxes & fees
2 Oct - 3 Oct
Oyster Bay Beach Resort
A pool area with lounge chairs and umbrellas, surrounded by palm trees, and a view of the sea.

3. JW Marriott St. Maarten Beach Resort & Spa

JW Marriott St. Maarten Beach Resort & Spa
5.0 star property
Oyster Pond
8.8 out of 10, Excellent, (410 reviews)
"The property was beautiful and the staff were so friendly and helpful."
United States
Aeryn
The price is S$519
includes taxes & fees
2 Oct - 3 Oct
JW Marriott St. Maarten Beach Resort & Spa
A clear blue pool with a white deck and palm trees, surrounded by a white fence and buildings in the background.

4. Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel
3.5 star property
Oyster Pond
9.2 out of 10, Wonderful, (1,000 reviews)
"The service was amazing and they didn’t miss a beat. The views are also incredible from the rooms."
United States
Jason
The price is S$280
includes taxes & fees
1 Nov - 2 Nov
Princess Heights Luxury Boutique Condo Hotel
A private pool with a view of a marina and buildings.

5. Les Balcons d'Oyster Pond

Les Balcons d'Oyster Pond
Oyster Pond
9.6 out of 10, Exceptional, (154 reviews)
"Beautiful setting, clean room, beautiful view, nice kitchen, nice balcony, easy to drive to Grand Case, Anse Marcel."
Canada
Adrian
Les Balcons d'Oyster Pond
A large swimming pool surrounded by palm trees and lounge chairs, with a hotel building in the background.

6. Dawn Beach Club Resort Sint Maarten

Dawn Beach Club Resort Sint Maarten
4.0 star property
Oyster Pond
8.8 out of 10, Excellent, (33 reviews)
"Large rooms with great ocean views! Helpful staff and good beach access!"
United States
Gavin
The price is S$965
includes taxes & fees
2 Oct - 3 Oct
Dawn Beach Club Resort Sint Maarten
A poolside area with lounge chairs and umbrellas, a person in a white robe, and a view of the sea and hills in the background.

7. Christopher Hotel

Christopher Hotel
5.0 star property
Pointe Milou
9.6 out of 10, Exceptional, (263 reviews)
"Great hotel"
United States
andres felipe
The price is S$1,443
includes taxes & fees
23 Oct - 24 Oct
Christopher Hotel
A resort with a pool, beach, and boats in the water.

8. GYP SEA Saint Barth

GYP SEA Saint Barth
5.0 star property
Colombier
9.8 out of 10, Exceptional, (105 reviews)
"Excellent service!!"
United States
Renee
GYP SEA Saint Barth
An infinity pool with a view of the ocean, outdoor dining area with tables and chairs, and palm trees.

9. Le Toiny Hôtel & Beach Club

Le Toiny Hôtel & Beach Club
5.0 star property
Toiny
9.8 out of 10, Exceptional, (56 reviews)
"Nice place to stay and the staff are very friendly"
United States
Keshia
The price is S$1,453
includes taxes & fees
15 Oct - 16 Oct
Le Toiny Hôtel & Beach Club
An aerial view of a beachfront resort with a swimming pool, beach umbrellas, and palm trees.

10. Pearl Beach Hotel

Pearl Beach Hotel
Saint-Jean
9.4 out of 10, Exceptional, (212 reviews)
"Amazing location, staff … beautiful hotel"
United States
Juan
The price is S$889
includes taxes & fees
2 Oct - 3 Oct
Pearl Beach Hotel
A person relaxing by a pool with a view of the ocean and mountains.

11. Amnios St Barth

Amnios St Barth
Grand Cul-de-Sac
9.6 out of 10, Exceptional, (129 reviews)
"We had a great experience in Saint "
United States
LILIBETH
Amnios St Barth
A poolside area with lounge chairs and a view of the ocean and a hillside with buildings.

12. Tropical Hotel St Barth

Tropical Hotel St Barth
5.0 star property
Saint-Jean
9.8 out of 10, Exceptional, (135 reviews)
"Perfect place and good location"
United States
Steven
Tropical Hotel St Barth
A clear blue pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

13. Le Barthélemy Hotel & Spa

Le Barthélemy Hotel & Spa
5.0 star property
Grand Cul-de-Sac
9.8 out of 10, Exceptional, (91 reviews)
"Everything there was amazing and the staff"
United States
Salvatore
The price is S$2,961
includes taxes & fees
22 Oct - 23 Oct
Le Barthélemy Hotel & Spa
A beach with rows of sun loungers under umbrellas, a rocky cliff in the background, and a clear blue sea.

14. Fouquet's Saint-Barth

Fouquet's Saint-Barth
5.0 star property
Lurin
9.6 out of 10, Exceptional, (38 reviews)
"Amazing hotel with wonderful staff."
United States
Vicente Jose
Fouquet's Saint-Barth
A poolside area with lounge chairs, a dining table with wine glasses, a bottle, and a pineapple.

15. Coral Beach Club Villas & Marina

Coral Beach Club Villas & Marina
4.0 star property
Oyster Pond
9.2 out of 10, Wonderful, (119 reviews)
"The condo and property was clean and well decorated and maintained. We had an awesome stay and will return."
United States
Donna
Coral Beach Club Villas & Marina
A stone staircase surrounded by lush greenery and potted plants.

16. Residence Adam & Eve

Residence Adam & Eve
Orient Bay
9.4 out of 10, Exceptional, (60 reviews)
"I had such a beautiful and relaxing stay! The bedroom was absolutely amazing, and the entire property was thoughtfully laid out and so inviting. The pool and hot tub were wonderfully warm, making it so easy to unwind and enjoy the space. The view was incredible and truly added to the experience. The location was also perfect—close to everything I needed while still feeling peaceful and comfortable. The hosts were wonderful as well. They were extremely responsive, helpful, and went above and...
Canada
Niagara Apex
The price is S$372
includes taxes & fees
15 Oct - 16 Oct
Residence Adam & Eve
A balcony with a sofa, a small table, a towel, and a plant.

17. Reve de Saint Barth

Reve de Saint Barth
Merlette
9.8 out of 10, Exceptional, (70 reviews)
"This place is a hidden gem, our host Ninon was always available to help and answer any questions. I would recommend this place to anyone visiting St Barths."
United States
Albert
Reve de Saint Barth
A balcony with a view of the ocean, two lounge chairs, a table with a bottle and glasses, and a small table with pastries.

18. Lil' Home

Lil' Home
Devet
9.8 out of 10, Exceptional, (18 reviews)
"The most beautiful villa, breathtaking views. The villa was impeccable clean and beautifully designed."
United States
Yoana
Lil' Home
A beachside resort with thatched umbrellas, lounge chairs, and a view of the ocean and distant hills.

19. Hotel Les Ondines Sur La Plage

Hotel Les Ondines Sur La Plage
Grand Cul-de-Sac
10.0 out of 10, Exceptional, (90 reviews)
"This was a wonderful stay, the attentive staff, cleanliness, breakfast and overall experience was just perfect! I would highly recommend this hotel & would gladly return!"
United States
claudia
Hotel Les Ondines Sur La Plage
A poolside view with a clear blue ocean, palm trees, and a mountainous backdrop.

20. Hotel Manapany

Hotel Manapany
5.0 star property
Anse des Cayes
9.4 out of 10, Exceptional, (71 reviews)
"Lovely, “barefoot chic” hotel that is top class in all respects"
United Kingdom
Quintin
Hotel Manapany
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 Leeward Hotel Reviews

Reve de Saint Barth

Reve de Saint Barth

10/10 Excellent
"I would like to thank Ninon for an great experience while visiting the property at Rêve de St. Barth. We appreciated the innovative architectural design and felt like we were special how the staff treated us. Lovely setting in the hills of St.Barth with a view of the ocean from the second floor bedroom. The accommodations can easily serve a family of 4 although we were there as a couples get away. Surprisingly this turned out to be the best vacation stay of the year 2026 for us so far. The island is quietly relaxing at this time of year. If I could make one recommendation for a vacation stay I would easily choose this hotel first and foremost. Thank you Ninon for allowing us to visit your private paradise. 🙏"
Scott 2-night trip
Posted 1 day ago
Reve de Saint Barth
Hotel Manapany

Hotel Manapany

10/10 Excellent
"Lovely, “barefoot chic” hotel that is top class in all respects"
Quintin 5-night trip
Posted 6 months ago
Hotel Manapany