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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 beds, 2.5 private bathrooms
16–21 Oct
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4.97 out of 5 average rating, 106 reviews
Superhost
Home in Koolbaai
Bahia - Villa 1
3 bedrooms, 3 beds, 2.5 bathrooms
14–19 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Simpson Bay
Ocean Breeze at Las Arenas
3 bedrooms, 3 king beds, 3.5 bathrooms
14–19 Jul
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Villa in Beacon Hill
Infinity Ocean Edge - Luxury Oceanfront Penthouse
3 bedrooms, 3 king beds, 3.5 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 24 reviews
Guest favourite
Townhouse in Sint Maarten
Indigo Bay Villa Poolside - Ocean 14
2 bedrooms, 2 king beds, 2.5 bathrooms
2–7 Oct
4.96 out of 5 average rating, 106 reviews
Superhost
Flat in Simpson Bay
Luxury Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
13–18 Jul
Top guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 65 reviews
Guest favourite
Flat in Cole Bay
Luxurious Sunset Lagoon View
2 bedrooms, 2 beds, 2.5 bathrooms
4–9 Aug
5.0 out of 5 average rating, 10 reviews
Guest favourite
Apartment in Simpson Bay
Beachfront Paradise with Pool & Stunning Sunsets
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
4.9 out of 5 average rating, 68 reviews
Top guest favourite
Flat in Simpson Bay
Le Papillon -Modern, beachfront, 550sq. ft terrace
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 51 reviews
Top guest favourite
Home in Simpson Bay
Villa Blue View .. stunning views of endless sea!
4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 92 reviews
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.99 out of 5 average rating, 97 reviews
Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds, 3 bathrooms
9–14 Aug
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Simpson Bay
Apartment on the beach 2
1 bedroom, 1 queen bed, 1 bathroom
28 Jul – 2 Aug
4.85 out of 5 average rating, 201 reviews
Guest favourite
Flat in Simpson Bay
OASIS Penthouse with private garden and Generator
2 bedrooms, 2 king beds, 2.5 bathrooms
13–18 Jul
4.92 out of 5 average rating, 52 reviews
Flat in Simpson Bay
Condo Josephine Maho Beacon Hill
2 bedrooms, 2 king beds, 1 bathroom
15–20 Jul
4.79 out of 5 average rating, 14 reviews
Guest favourite
Flat in Cole Bay
Beautiful, bright apartment with a lagoon view in Simpson Bay
1 bedroom, 2 beds, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Koolbaai
Pelican key - BEACH FRONT Villa
3 bedrooms, 5 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 43 reviews
Guest favourite
Flat in Simpson Bay
Top of the art penthouse
3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Aug
4.95 out of 5 average rating, 111 reviews