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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Villa in Simpson Bay, Sint Maarten
Waterfront "Bonjour" Beacon Hill St Maarten
4 bedrooms, 4 beds, 4 private bathrooms
7–12 Jul
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4.97 out of 5 average rating, 86 reviews
Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds
6–11 Jul
5.0 out of 5 average rating, 39 reviews
Guest favourite
Home in Cole Bay, Sint Maarten
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds
27 Jul – 1 Aug
5.0 out of 5 average rating, 55 reviews
Top guest favourite
Villa in Cole Bay, Sint Maarten
[Sunset Place] 3BR Oceanfront Villa, Private Pool
3 bedrooms, 3 beds
27 Jul – 1 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds
31 Jul – 5 Aug
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Villa in Philipsburg, Sint Maarten
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds
21–26 Sept
4.99 out of 5 average rating, 328 reviews
Guest favourite
Villa in Indigo bay, Sint Maarten, Sint Maarten
Ocean Dream Villa
2 bedrooms, 2 queen beds
13–18 Sept
4.95 out of 5 average rating, 64 reviews
Guest favourite
Townhouse in Sint Maarten, Sint Maarten
Indigo Bay Villa Poolside - Ocean 14
2 bedrooms, 2 king beds
2–7 Oct
4.96 out of 5 average rating, 106 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds
18–23 Aug
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Koolbaai, Sint Maarten
Blue Palm Estate Townhouse w/ Ocean View
2 bedrooms, 3 beds
14–19 Jul
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Flat in St Martin, St Martin
07 yellow cliff
2 bedrooms, 2 queen beds
5–10 Jul
5.0 out of 5 average rating, 23 reviews
Guest favourite
Villa in Indigo Bay, Sint Maarten
Villa Ocean - Indulge Yourself in Paradise
3 bedrooms, 4 beds
7–12 Sept
4.95 out of 5 average rating, 77 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Ocean Breeze at Las Arenas
3 bedrooms, 3 king beds
7–12 Jul
4.97 out of 5 average rating, 33 reviews
Luxe
Home in Lowlands, Sint Maarten
Brand NEW - Waterfront Villa - Pool
4 bedrooms, 4 double beds
6–11 Jul
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 king beds
16–21 Oct
4.97 out of 5 average rating, 106 reviews
Top guest favourite
Flat in Cole Bay, Sint Maarten
Beautiful, bright apartment with a lagoon view in Simpson Bay
1 bedroom, 2 beds
19–24 Aug
5.0 out of 5 average rating, 14 reviews
Flat in Simpson Bay, Sint Maarten
Apartment in Simpson bay
1 bedroom, 2 double beds
10–15 Jul
New place to stay
Superhost
Flat in Cole Bay, Sint Maarten
Sunny Marina Residence
3 bedrooms, 4 beds
19–24 Jul
4.83 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
The Beach House Apartment
1 bedroom, 1 king bed
1–6 Aug
5.0 out of 5 average rating, 245 reviews