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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
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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
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
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
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
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
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
Apartment in Simpson Bay
SkyPort Condo
2 bedrooms, 2 beds, 2 bathrooms
23–28 Jul
4.97 out of 5 average rating, 79 reviews
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
Superhost
Serviced apartment in Simpson Bay
Unit 7 - Luxury apartment by the sea
1 bedroom, 1 king bed, 1 bathroom
4–9 Aug
4.92 out of 5 average rating, 73 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
Superhost
Serviced apartment in Simpson Bay
Unit 3 - Luxury apartment by the sea
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
4.85 out of 5 average rating, 52 reviews
Top guest favourite
Home in Koolbaai
Pelican key - BEACH FRONT Villa
3 bedrooms, 5 beds, 3.5 bathrooms
11–16 Jul
5.0 out of 5 average rating, 43 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, 133 reviews