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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Villa in Simpson Bay
Waterfront "Bonjour" Beacon Hill St Maarten
4 bedrooms, 4 beds, 4 private bathrooms
9–14 Sept
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4.97 out of 5 average rating, 86 reviews
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
1 bedroom, 1 king bed
1–6 Aug
5.0 out of 5 average rating, 246 reviews
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds
3–8 Aug
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds
20–25 Jul
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds
12–17 Jul
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds
9–14 Aug
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Flat in Simpson Bay
Apartment on the beach 2
1 bedroom, 1 queen bed
11–16 Jul
4.85 out of 5 average rating, 201 reviews
Guest favourite
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
1 bedroom, 1 bed
28 Jul – 2 Aug
4.89 out of 5 average rating, 132 reviews
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds
27 Jul – 1 Aug
5.0 out of 5 average rating, 40 reviews
Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds
17–22 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds
2–7 Aug
4.9 out of 5 average rating, 51 reviews
Top guest favourite
Flat in Simpson Bay
Lilly's Beach
1 bedroom, 1 king bed
21–26 Aug
4.95 out of 5 average rating, 236 reviews
Top guest favourite
Apartment in Simpson Bay
SkyPort Condo
2 bedrooms, 2 beds
16–21 Jul
4.97 out of 5 average rating, 79 reviews
Guest favourite
Apartment in Simpson Bay
1 Bedroom Seafront Flat D3
1 bedroom, 1 bed
14–19 Jul
5.0 out of 5 average rating, 15 reviews
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 55 reviews
Superhost
Hotel in Upper Prince's Quarter
Panorama SXM - 1 BR Ocean View - Luxury Apartment
1 bedroom, 1 king bed
12–17 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 king beds
16–21 Oct
4.97 out of 5 average rating, 106 reviews
Top guest favourite
Guest house in Simpson Bay
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 queen bed
4–9 Aug
4.95 out of 5 average rating, 108 reviews
Top guest favourite
Apartment in Lowlands
Maho 1 Bed Condo with ocean view & Free Wi-Fi
1 bedroom, 2 beds
28 Aug – 2 Sept
4.9 out of 5 average rating, 52 reviews