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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 Middle Floor - Unit 2
3 bedrooms, 3 beds, 3.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 31 reviews
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
8–13 Jul
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
19–24 Jul
4.99 out of 5 average rating, 328 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
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
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
Guest favourite
Villa in Indigo bay, Sint Maarten
Ocean Dream Villa
2 bedrooms, 2 queen beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 64 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, 9 reviews
Luxe
Home in Lowlands
Brand NEW - Waterfront Villa - Pool
4 bedrooms, 4 double beds, 4 bathrooms
8–13 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
31 Jul – 5 Aug
5.0 out of 5 average rating, 55 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
Top guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 64 reviews
Guest favourite
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
1 bedroom, 1 bed, 1 bathroom
28 Jul – 2 Aug
4.89 out of 5 average rating, 132 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
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, 37 reviews
Top guest favourite
Apartment in Simpson Bay
SeaShores Beach Front 1 Brm Apt With Generator SXM
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Apartment in Simpson Bay
Ocean Breeze at Las Arenas
3 bedrooms, 3 king beds, 3.5 bathrooms
10–15 Jul
4.97 out of 5 average rating, 33 reviews
Guest favourite
Apartment in Koolbaai
Blue Pelican Luxury Villa - Featured on HGTV!
1 bedroom, 1 bed, 1 bathroom
21–26 Jul
5.0 out of 5 average rating, 10 reviews