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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 beds, 2.5 private bathrooms
16–21 Oct
,
4.97 out of 5 average rating, 106 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, 244 reviews
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
3 bedrooms, 3 beds, 3.5 bathrooms
6–11 Jul
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds, 4 bathrooms
9–14 Aug
5.0 out of 5 average rating, 20 reviews
Flat in Lowlands
Luxury Studio| Walk to Maho Beach, Casino, Dinning
1 bedroom, 1 queen bed, 1 bathroom
28 Jul – 2 Aug
New place to stay
Guest favourite
Flat in Simpson Bay
Apartment on the beach
1 bedroom, 1 queen bed, 1 bathroom
23–28 Jul
4.88 out of 5 average rating, 243 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, 25 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
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 64 reviews
Guest favourite
Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
11–16 Aug
4.86 out of 5 average rating, 259 reviews
Top guest favourite
Apartment in Simpson Bay
SkyPort Condo
2 bedrooms, 2 beds, 2 bathrooms
23–28 Jul
4.97 out of 5 average rating, 79 reviews
Hotel in Upper Prince's Quarter
Panorama SXM - 1 BR Ocean View - Luxury Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
4–9 Jul
New place to stay
Top guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Apartment in pelican key
Spacious 2 bedroom in Pelican Key near the beach.
2 bedrooms, 2 beds, 2 bathrooms
7–12 Jul
4.83 out of 5 average rating, 59 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, 50 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
Private Pool- 5 min DRIVE to Maho Beach & Airport
1 bedroom, 1 queen bed, 1 bathroom
4–9 Jul
4.96 out of 5 average rating, 71 reviews
Top guest favourite
Flat in Simpson Bay
Le Papillon -Modern, beachfront, 550sq. ft terrace
2 bedrooms, 2 king beds, 2.5 bathrooms
21–26 Aug
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Simpson Bay
Simpson Bay Beach 3 Bedroom with pool
3 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
4.92 out of 5 average rating, 12 reviews