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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Villa in Simpson Bay
Waterfront "Bonjour" Beacon Hill St Maarten
4 bedrooms, 4 beds, 4 private bathrooms
22–27 Oct
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4.97 out of 5 average rating, 91 reviews
Guest favourite
Flat in Simpson Bay
Private Pool- 5 min DRIVE to Maho Beach & Airport
1 bedroom, 1 queen bed, 1 bathroom
17–22 Sept
4.96 out of 5 average rating, 76 reviews
Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
7–12 Sept
4.91 out of 5 average rating, 57 reviews
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 83 reviews
Guest favourite
Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
24–29 Sept
4.87 out of 5 average rating, 273 reviews
Superhost
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.87 out of 5 average rating, 142 reviews
Guest favourite
Flat in Simpson Bay
Apartment on the beach
Individual host
5–10 Sept
4.89 out of 5 average rating, 246 reviews
Guest favourite
Flat in Simpson Bay
Unit 7 - Luxury apartment by the sea
1 bedroom, 1 king bed, 1 bathroom
16–21 Sept
4.93 out of 5 average rating, 80 reviews
Top guest favourite
Flat in Lowlands
Stunning Gem in Prime Location
1 bedroom, 2 beds, 2 bathrooms
7–12 Sept
4.92 out of 5 average rating, 51 reviews
Guest favourite
Flat in Simpson Bay
Royal Palm Hilton SXM
2 bedrooms, 3 beds, 2 bathrooms
7–14 Sept
4.92 out of 5 average rating, 66 reviews
Guest favourite
Room in Upper Prince's Quarter
1BR Luxury Apartment | Ocean View
1 king bed, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.99 out of 5 average rating, 104 reviews
Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 king beds, 2.5 bathrooms
24–29 Apr
4.96 out of 5 average rating, 109 reviews
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
24–29 Sept
5.0 out of 5 average rating, 252 reviews
Townhouse in Simpson Bay
The Drake’s "Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds, 3 bathrooms
6–11 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
Individual host
27 Sept – 2 Oct
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
11–16 Sept
4.99 out of 5 average rating, 335 reviews
Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds, 3 bathrooms
1–6 Oct
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Simpson Bay
Second Home Beach Apartment
Individual host
20–25 Sept
4.99 out of 5 average rating, 106 reviews