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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
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 64 reviews
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 246 reviews
Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds, 3 bathrooms
9–14 Aug
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds, 4 bathrooms
12–17 Jul
5.0 out of 5 average rating, 20 reviews
Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds, 5.5 bathrooms
17–22 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Sept
5.0 out of 5 average rating, 40 reviews
Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
2–7 Aug
4.9 out of 5 average rating, 51 reviews
Top guest favourite
Apartment in Lowlands
Saint Maarten La Terrasse Maho
2 beds, 1 bathroom
31 Jul – 5 Aug
4.95 out of 5 average rating, 134 reviews
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
3–8 Aug
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Flat in Simpson Bay
Apartment on the beach 2
1 bedroom, 1 queen bed, 1 bathroom
28 Jul – 2 Aug
4.85 out of 5 average rating, 201 reviews
Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 king beds, 2.5 bathrooms
16–21 Oct
4.97 out of 5 average rating, 106 reviews
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 55 reviews
Guest favourite
Apartment in Simpson Bay
1 Bedroom Seafront Flat D3
1 bedroom, 1 bed, 1 bathroom
14–19 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Flat in Simpson Bay
Lilly's Beach
1 bedroom, 1 king bed, 1 bathroom
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, 2 bathrooms
16–21 Jul
4.97 out of 5 average rating, 79 reviews
Guest favourite
Flat in Simpson Bay
Top of the art penthouse
3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Aug
4.95 out of 5 average rating, 111 reviews
Top guest favourite
Apartment in Lowlands
Maho 1 Bed Condo with ocean view & Free Wi-Fi
1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept
4.9 out of 5 average rating, 52 reviews
Flat in Simpson Bay
Paradise by the Sea
2 bedrooms, 2 beds, 2.5 bathrooms
18–23 Jul
5.0 out of 5 average rating, 4 reviews