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Search results; Over 1,000 homes in Simpson Bay

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, 107 reviews
Top guest favourite
Villa in Sint Maarten, Sint Maarten
Indigo Oceanfront Condo Poolside - Unit 1
3 bedrooms, 3 beds
25–30 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Apartment in Simpson Bay, Sint Maarten
SkyPort Condo
2 bedrooms, 2 beds
2–7 Sept
4.98 out of 5 average rating, 81 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
Superhost
Home in Les Terres Basses, St Martin
Tiki Lodge 5mn away from the beach
3 bedrooms, 3 beds
1–6 Aug
Villa in Orient Bay, St Martin
Villa Turquoze - An amazing view on Orient Beach
4 bedrooms, 4 king beds
14–19 Aug
New place to stay
Top guest favourite
Villa in Little Bay, Sint Maarten
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds
8–13 Sept
4.99 out of 5 average rating, 98 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
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
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, 25 reviews
Townhouse in Simpson Bay, Sint Maarten
Nirvana @ The Drake | Beach Just Steps Away
2 bedrooms, 3 beds
4–9 Aug
New place to stay
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
Superhost
Home in Cul-de-Sac, St Martin
Villa ELIOS 2BR SeaView
2 bedrooms, 2 king beds
23–28 Aug
New place to stay
Home in Marigot, St Martin
House with sea view, 3 bedrooms, beach and pool access
3 bedrooms, 3 beds
11–16 Aug
5.0 out of 5 average rating, 5 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
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
Guest favourite
Flat in Cole Bay, Sint Maarten
C354 - Top view with balcony
1 bedroom, 1 king bed
31 Aug – 5 Sept
4.93 out of 5 average rating, 14 reviews
Guest favourite
Flat in Simpson Bay, Sint Maarten
Dolphin - cosy 2BR apt, 50m Simpson Bay beach
2 bedrooms, 3 beds
1–8 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Room in Simpson Bay, Sint Maarten
Book your solo stay close to beaches & hotspots
1 double bed
15–20 Aug
5.0 out of 5 average rating, 8 reviews