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
5.0 out of 5 average rating, 244 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
1–6 Aug
Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
5.0 out of 5 average rating, 20 reviews, 4 bedrooms, 5 beds, 4 bathrooms
9–14 Aug
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
5.0 out of 5 average rating, 39 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Jul
Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5.0 out of 5 average rating, 25 reviews, 5 bedrooms, 5 beds, 5.5 bathrooms
17–22 Jul
Hotel in Upper Prince's Quarter
Panorama SXM - 1 BR Ocean View - Luxury Apartment
New place to stay, 1 bedroom, 1 bed, 1.5 bathrooms
5–10 Jul
Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
4.92 out of 5 average rating, 24 reviews, 3 bedrooms, 3 beds, 3 bathrooms
9–14 Aug
Guest favourite
Apartment in Simpson Bay
1 Bedroom Seafront Flat D3
5.0 out of 5 average rating, 15 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Jul
Top guest favourite
Flat in Simpson Bay
Villa Harmony Haven
5.0 out of 5 average rating, 64 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
28 Jul – 2 Aug
Top guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
5.0 out of 5 average rating, 76 reviews, 2 beds, 1.5 bathrooms
1–6 Sept
Guest favourite
Flat in Simpson Bay
Apartment on the beach
4.88 out of 5 average rating, 242 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Jul
Superhost
Serviced apartment in Simpson Bay
Unit 3 - Luxury apartment by the sea
4.84 out of 5 average rating, 51 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Top guest favourite
Flat in Simpson Bay
Simpson Bay Beach 3 Bedroom with pool
4.92 out of 5 average rating, 12 reviews, 3 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
Top guest favourite
Home in Koolbaai
Pelican key - BEACH FRONT Villa
5.0 out of 5 average rating, 42 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
11–16 Jul
Guest favourite
Townhouse in Koolbaai
Quiet Family 3BR Villa, Private Pool · Pelican Key
4.85 out of 5 average rating, 55 reviews, 3 bedrooms, 5 beds, 3 bathrooms
19–24 Jul
Flat in Lowlands
Luxury Studio| Walk to Maho Beach, Casino, Dinning
New place to stay, 1 bedroom, 1 bed, 1 bathroom
8–13 Jul
Superhost
Serviced apartment in Simpson Bay
Unit 7 - Luxury apartment by the sea
4.92 out of 5 average rating, 73 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Aug
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
5.0 out of 5 average rating, 55 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
2–7 Aug
Guest favourite
Flat in Cole Bay
Luxurious Sunset Lagoon View
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
17–22 Aug