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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
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
3–8 Aug
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 246 reviews
Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds, 4 bathrooms
12–17 Jul
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Flat in Simpson Bay
Apartment on the beach 2
1 bedroom, 1 queen bed, 1 bathroom
10–15 Jul
4.85 out of 5 average rating, 201 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
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 64 reviews
Guest favourite
Apartment in Simpson Bay
1 Bedroom Seafront Flat D3
1 bedroom, 1 bed, 1 bathroom
14–19 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 40 reviews
Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds, 5.5 bathrooms
17–22 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
2–7 Aug
4.9 out of 5 average rating, 51 reviews
Top guest favourite
Flat in Simpson Bay
Lilly's Beach
1 bedroom, 1 king bed, 1 bathroom
21–26 Aug
4.95 out of 5 average rating, 236 reviews
Top guest favourite
Apartment in Simpson Bay
SkyPort Condo
2 bedrooms, 2 beds, 2 bathrooms
16–21 Jul
4.97 out of 5 average rating, 79 reviews
Guest favourite
Flat in Simpson Bay
Private Pool- 5 min DRIVE to Maho Beach & Airport
1 bedroom, 1 queen bed, 1 bathroom
20–25 Jul
4.96 out of 5 average rating, 71 reviews
Superhost
Hotel in Upper Prince's Quarter
Panorama SXM - 1 BR Ocean View - Luxury Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 3 reviews
Superhost
Flat in Simpson Bay
Luxury Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Jul
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
Apartment in Simpson Bay
Hamaka condo, a beachfront retreat on Simpson Bay
1 bedroom, 2 beds, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 103 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