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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Guesthouse in Simpson Bay, Sint Maarten
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 bed, 1 private bath
Aug 14–19
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4.95 out of 5 average rating, 108 reviews
Top guest favourite
Loft in Marigot, St Martin
Sea Loft, Breathtaking View – Private Pool
2 bedrooms, 2 beds, 2 baths
Oct 14–19
4.99 out of 5 average rating, 198 reviews
Superhost
Apartment in Saint Martin, St Martin
Experience a luxurious break by the sea
1 bedroom, 1 king bed, 1 bath
Sep 6–11
New place to stay
Superhost
Condo in Upper Prince's Quarter, Sint Maarten
Serenity Seascape | 2BR Retreat, 270° Oceanviews
2 bedrooms, 2 king beds, 2.5 baths
Sep 4–9
5.0 out of 5 average rating, 4 reviews
Guest favourite
Apartment in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 baths
Sep 7–12
5.0 out of 5 average rating, 80 reviews
Guest favourite
Apartment in Simpson Bay, Sint Maarten
Private Pool- 5 min DRIVE to Maho Beach & Airport
1 bedroom, 1 queen bed, 1 bath
Aug 21–26
4.96 out of 5 average rating, 73 reviews
Top guest favourite
Villa in Philipsburg, Sint Maarten
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 baths
Apr 10–15
4.99 out of 5 average rating, 331 reviews
Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Poolside - Unit 1
3 bedrooms, 3 beds, 3.5 baths
Oct 3–8
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Home in Koolbaai, Sint Maarten
Blue Palm Estate Townhouse w/ Ocean View
2 bedrooms, 3 beds, 3 baths
Aug 12–17
4.95 out of 5 average rating, 22 reviews
Guest favourite
Apartment in Little Bay, Sint Maarten
Stunning 2 BD Ocean View - Terraces Lt Bay
2 bedrooms, 3 beds, 2 baths
Sep 8–13
4.99 out of 5 average rating, 186 reviews
Top guest favourite
Apartment in Grand Cayes, St Martin
Modern Sea View Apartment from Pinel island
1 bedroom, 1 queen bed, 1 bath
Aug 26–31
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Condo in Simpson Bay, Sint Maarten
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds, 3 baths
Aug 13–18
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Condo in Simpson Bay, Sint Maarten
Deep Blue Sea at LaSiesta - Oceanfront Condo
1 bedroom, 3 beds, 1 bath
Aug 12–17
4.91 out of 5 average rating, 11 reviews
Townhouse in Simpson Bay, Sint Maarten
Utopia A3 | Beachside Stay @ The Drake Residences
2 bedrooms, 3 beds, 2.5 baths
Sep 8–13
5.0 out of 5 average rating, 3 reviews
Home in Koolbaai, Sint Maarten
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds, 2.5 baths
Aug 16–21
New place to stay
Guest favourite
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and pool access
3 bedrooms, 3 beds, 3 baths
Sep 14–19
5.0 out of 5 average rating, 5 reviews
Guest favourite
Apartment in Simpson Bay, Sint Maarten
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 baths
Sep 7–12
4.91 out of 5 average rating, 55 reviews
Guest favourite
Condo in Lowlands, Sint Maarten
It’s all about Love...St. Maarten
2 bedrooms, 2 beds, 2 baths
Aug 15–20
4.95 out of 5 average rating, 57 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Condo in Simpson Bay Yacht Club
1 bedroom, 1 king bed, 1 bath
Aug 20–25
4.92 out of 5 average rating, 26 reviews