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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 beds, 2.5 private bathrooms
1–6 Oct
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4.96 out of 5 average rating, 108 reviews
Superhost
Apartment in Upper Prince's Quarter, Sint Maarten
Serenity Seascape | 2BR Retreat, 270° Oceanviews
2 bedrooms, 2 king beds
8–13 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Koolbaai, Sint Maarten
Bahia - Villa 1
3 bedrooms, 3 beds
3–8 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds
8–13 Aug
5.0 out of 5 average rating, 78 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, 42 reviews
Top guest favourite
Flat in Grand Cayes, St Martin
Modern Sea View Apartment from Pinel island
1 bedroom, 1 queen bed
13–18 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds
5–10 Aug
5.0 out of 5 average rating, 67 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Ocean Breeze at Las Arenas
3 bedrooms, 3 king beds
1–6 Aug
4.97 out of 5 average rating, 33 reviews
Guest favourite
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and pool access
3 bedrooms, 3 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds
9–14 Aug
4.92 out of 5 average rating, 26 reviews
Townhouse in Simpson Bay, Sint Maarten
The Drake's "Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds
2–7 Aug
New place to stay
Top guest favourite
Home in Koolbaai, Sint Maarten
Pelican key - BEACH FRONT Villa
3 bedrooms, 5 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Upper Prince's Quarter, Sint Maarten
Breathtaking views of St Barth - 8 people
4 bedrooms, 4 beds
1–6 Aug
4.96 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
27 Aug – 1 Sept
5.0 out of 5 average rating, 249 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
Beachfront Caribbean Breeze in Paradise, SXM
2 bedrooms, 2 king beds
1–6 Aug
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Flat in Simpson Bay, Sint Maarten
Le Papillon -Modern, beachfront, 550sq. ft terrace
2 bedrooms, 2 king beds
1–6 Oct
5.0 out of 5 average rating, 52 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds
2–7 Aug
4.91 out of 5 average rating, 53 reviews
Superhost
Flat in Simpson Bay, Sint Maarten
Luxury Beachfront Condo
2 bedrooms, 2 beds
1–6 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Apartment in Simpson Bay, Sint Maarten
1 Bedroom Seafront Flat D3
1 bedroom, 1 bed
1–6 Aug
5.0 out of 5 average rating, 16 reviews