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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Guest house in Simpson Bay, Sint Maarten
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 bed, 1 private bathroom
20–25 Aug
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4.95 out of 5 average rating, 109 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds
7–12 Sept
5.0 out of 5 average rating, 81 reviews
Top guest favourite
Loft in Marigot, St Martin
Sea Loft, Breathtaking View – Private Pool
2 bedrooms, 2 beds
14–19 Oct
4.99 out of 5 average rating, 199 reviews
Home in Koolbaai, Sint Maarten
Waterfront paradise facing the ocean SXM
Individual host
1–6 Sept
New place to stay
Top guest favourite
Apartment in Upper Prince's Quarter, Sint Maarten
Serenity Seascape | 2BR Retreat, 270° Oceanviews
2 bedrooms, 2 king beds
24–29 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
Private Pool- 5 min DRIVE to Maho Beach & Airport
1 bedroom, 1 queen bed
30 Aug – 4 Sept
4.96 out of 5 average rating, 75 reviews
Guest favourite
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and swimming pool access
Individual host
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Maho Beach, Sint Maarten
Turtle Den YOUR Maho Escape!
1 bedroom, 1 bed
28 Sept – 3 Oct
4.88 out of 5 average rating, 139 reviews
Guest favourite
Villa in Indigo bay, Sint Maarten, Sint Maarten
Ocean Dream Villa
2 bedrooms, 2 queen beds
12–17 Sept
4.94 out of 5 average rating, 70 reviews
Guest favourite
Flat in Little Bay, Sint Maarten
Stunning 2 BD Ocean View - Terraces Lt Bay
2 bedrooms, 3 beds
8–13 Sept
4.99 out of 5 average rating, 186 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds
7–12 Sept
4.91 out of 5 average rating, 56 reviews
Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Poolside - Unit 1
3 bedrooms, 3 beds
3–8 Oct
4.98 out of 5 average rating, 45 reviews
Top guest favourite
Villa in Cole Bay, Sint Maarten
[Sunset Place] 3BR Oceanfront Villa, Private Pool
3 bedrooms, 3 beds
3–8 Oct
5.0 out of 5 average rating, 13 reviews
Guest favourite
Flat in Grand-Case, St Martin
NEW: Unmatched Oceanfront Living in Grand Case
2 bedrooms, 2 beds
24–29 Aug
4.88 out of 5 average rating, 26 reviews
Top guest favourite
Home in Koolbaai, Sint Maarten
Blue Palm Estate Townhouse w/ Ocean View
2 bedrooms, 3 beds
20–25 Aug
4.95 out of 5 average rating, 22 reviews
Home in Koolbaai, Sint Maarten
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds
26–31 Aug
New place to stay
Guest favourite
Flat in Upper Prince's Quarter, Sint Maarten
Aman_Luna
2 bedrooms, 3 beds
1–6 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Grand Cayes, St Martin
Modern Sea View Apartment from Pinel island
1 bedroom, 1 queen bed
26–31 Aug
5.0 out of 5 average rating, 33 reviews
Townhouse in Simpson Bay, Sint Maarten
Tranquility A2 | Beachside @ The Drake Residences
2 bedrooms, 3 beds
30 Aug – 4 Sept