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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 beds, 3 private bathrooms
9–14 Aug
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4.92 out of 5 average rating, 24 reviews
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds, 3.5 bathrooms
6–11 Jul
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
31 Jul – 5 Aug
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Villa in Cole Bay
[Sunset Place] 3BR Oceanfront Villa, Private Pool
3 bedrooms, 3 beds, 3 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Villa in Indigo bay, Sint Maarten
Ocean Dream Villa
2 bedrooms, 2 queen beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 64 reviews
Top guest favourite
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
21–26 Sept
4.99 out of 5 average rating, 328 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
Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds, 4 bathrooms
18–23 Aug
5.0 out of 5 average rating, 20 reviews
Flat in Simpson Bay
Luxury Beachfront Condo
2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Jul
Luxe
Home in Lowlands
Brand NEW - Waterfront Villa - Pool
4 bedrooms, 4 double beds, 4 bathrooms
6–11 Jul
5.0 out of 5 average rating, 24 reviews
Guest favourite
Villa in Indigo Bay
Villa Ocean - Indulge Yourself in Paradise
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 77 reviews
Top guest favourite
Home in Koolbaai
Blue Palm Estate Townhouse w/ Ocean View
2 bedrooms, 3 beds, 3 bathrooms
14–19 Jul
4.95 out of 5 average rating, 21 reviews
Top 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
Flat in Simpson Bay
Apartment in Simpson bay
1 bedroom, 2 double beds, 1 bathroom
10–15 Jul
New place to stay
Top guest favourite
Apartment in Simpson Bay
Ocean Breeze at Las Arenas
3 bedrooms, 3 king beds, 3.5 bathrooms
6–11 Jul
4.97 out of 5 average rating, 33 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, 245 reviews
Guest favourite
Flat in Upper Prince's Quarter
Aman_Aria
2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 36 reviews
Guest favourite
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
1 bedroom, 1 bed, 1 bathroom
28 Jul – 2 Aug
4.88 out of 5 average rating, 130 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
16–21 Oct
4.97 out of 5 average rating, 106 reviews