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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Guest house in Simpson Bay
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 bed, 1 private bathroom
1–6 Sept
,
4.95 out of 5 average rating, 109 reviews
Guest favourite
Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
7–12 Sept
4.87 out of 5 average rating, 269 reviews
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
2–7 Sept
5.0 out of 5 average rating, 81 reviews
Guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool C2.1
Individual host
6–11 Sept
4.89 out of 5 average rating, 19 reviews
Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 68 reviews
Guest favourite
Flat in Simpson Bay
Unit 7 - Luxury apartment by the sea
1 bedroom, 1 king bed, 1 bathroom
1–6 Sept
4.93 out of 5 average rating, 80 reviews
Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds, 5.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 28 reviews
Guest favourite
Room in Upper Prince's Quarter
1BR Luxury Apartment | Ocean View
1 king bed, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Flat in Simpson Bay
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 bathroom
1–6 Sept
4.94 out of 5 average rating, 32 reviews
Superhost
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.87 out of 5 average rating, 141 reviews
Top guest favourite
Flat in Simpson Bay
Second Home Beach Apartment
Individual host
20–25 Sept
4.99 out of 5 average rating, 106 reviews
Top guest favourite
Apartment in Maho
Maho Love Shack:Unwind by the Rooftop Pool&Hot Tub
1 bedroom, 1 queen bed, 1 bathroom
1–6 Sept
4.91 out of 5 average rating, 255 reviews
Guest favourite
Flat in Simpson Bay
Apartment on the beach
Individual host
5–10 Sept
4.89 out of 5 average rating, 245 reviews
Guest favourite
Flat in Simpson Bay
Unit 3 - Luxury apartment by the sea
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
4.85 out of 5 average rating, 55 reviews
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Middle Floor - Unit 2
3 bedrooms, 3 beds, 3.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
24–29 Sept
5.0 out of 5 average rating, 251 reviews
Top guest favourite
Place to stay in Simpson Bay
Your floating B&B at SXM
Individual host
2–7 Dec
5.0 out of 5 average rating, 29 reviews
Townhouse in Simpson Bay
The Drake's "Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds, 3 bathrooms
1–6 Sept
Guest favourite
Flat in Lowlands
Luxury Studio| Walk to Maho Beach, Casino, Dinning
1 bedroom, 1 queen bed, 1 bathroom
2–7 Sept
5.0 out of 5 average rating, 7 reviews