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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 beds, 2.5 private bathrooms
1–6 Oct
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4.96 out of 5 average rating, 107 reviews
Guest favourite
Flat in Simpson Bay
Apartment on the beach
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.88 out of 5 average rating, 243 reviews
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
1 bedroom, 1 king bed, 1.5 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 248 reviews
Top guest favourite
Apartment in Simpson Bay
Beachfront Caribbean Breeze in Paradise, SXM
2 bedrooms, 2 king beds, 2.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 40 reviews
Guest favourite
Flat in Cole Bay
SXM Beachfront Escape
1 bedroom, 1 king bed, 1 bathroom
1–6 Aug
4.93 out of 5 average rating, 15 reviews
Guest favourite
Flat in Cole Bay
B243 - Deluxe 1 Bedroom
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.86 out of 5 average rating, 21 reviews
Guest favourite
Flat in Simpson Bay
Condo Josephine Maho Beacon Hill
2 bedrooms, 2 king beds, 1 bathroom
1–6 Aug
4.81 out of 5 average rating, 16 reviews
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, 238 reviews
Guest favourite
Flat in Simpson Bay
Private Pool- 5 min DRIVE to Maho Beach & Airport
1 bedroom, 1 queen bed, 1 bathroom
10–15 Aug
4.96 out of 5 average rating, 72 reviews
Guest favourite
Serviced apartment in Simpson Bay
Unit 3 - Luxury apartment by the sea
1 bedroom, 2 beds, 1 bathroom
1–6 Aug
4.85 out of 5 average rating, 53 reviews
Guest favourite
Flat in Simpson Bay
Garden View Simpson Bay -shared pool and Generator
1 bedroom, 2 beds, 1 bathroom
1–6 Aug
4.9 out of 5 average rating, 49 reviews
Guest favourite
Flat in Simpson Bay
Le Petit Paradis – Beachfront 1 Bedroom Apartment
1 bedroom, 1 queen bed, 1 bathroom
3–8 Aug
4.93 out of 5 average rating, 151 reviews
Top guest favourite
Flat in Simpson Bay
The Pineapple Suite
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Aug
4.96 out of 5 average rating, 45 reviews
Top guest favourite
Serviced apartment in Lowlands
Garden Side 2 Large Studio
1 queen bed, 1 bathroom
1–6 Aug
4.97 out of 5 average rating, 149 reviews
Guest favourite
Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
11–16 Aug
4.87 out of 5 average rating, 263 reviews
Guest favourite
Apartment in Lowlands
Maho studio overlooking airport, Free Wi-Fi!
1 bed, 1 bathroom
5–10 Aug
4.84 out of 5 average rating, 99 reviews
Guest favourite
Room in Upper Prince's Quarter
Panorama SXM - 1 BR Ocean View - Luxury Apartment
1 king bed, 1.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 5 reviews
Townhouse in Simpson Bay
Nirvana @ The Drake | Beach Just Steps Away
2 bedrooms, 3 beds, 2.5 bathrooms
4–9 Aug
New place to stay
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
8–13 Sept
4.99 out of 5 average rating, 98 reviews