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Search results; Over 1,000 homes in Simpson Bay

Superhost
Apartment in Simpson Bay
Oceanfront w Pool | Maho Beach area
1 bedroom, 2 beds, 1.5 private bathrooms
23–28 Aug
,
4.8 out of 5 average rating, 189 reviews
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
5.0 out of 5 average rating, 248 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
29 Sept – 4 Oct
Top guest favourite
Flat in Simpson Bay
Second Home Beach Apartment
4.99 out of 5 average rating, 102 reviews, 1 bedroom, 1 bed, 1 bathroom
20–25 Sept
Guest favourite
Flat in Simpson Bay
Apartment on the beach
4.88 out of 5 average rating, 243 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Flat in Simpson Bay
Condo Josephine Maho Beacon Hill
4.81 out of 5 average rating, 16 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Apartment in Simpson Bay
Beachfront Caribbean Breeze in Paradise, SXM
5.0 out of 5 average rating, 40 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
1–6 Aug
Guest favourite
Flat in Cole Bay
B243 - Deluxe 1 Bedroom
4.86 out of 5 average rating, 21 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Flat in Simpson Bay
Garden View Simpson Bay -shared pool and Generator
4.9 out of 5 average rating, 49 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Apartment in Lowlands
Maho studio overlooking airport, Free Wi-Fi!
4.84 out of 5 average rating, 99 reviews, 1 bed, 1 bathroom
5–10 Aug
Guest favourite
Flat in Simpson Bay
Private Pool- 5 min DRIVE to Maho Beach & Airport
4.96 out of 5 average rating, 72 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Guest favourite
Flat in Simpson Bay
Lilly's Beach
4.95 out of 5 average rating, 238 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Aug
Guest favourite
Serviced apartment in Simpson Bay
Unit 3 - Luxury apartment by the sea
4.85 out of 5 average rating, 53 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Serviced apartment in Lowlands
Garden Side 2 Large Studio
4.97 out of 5 average rating, 149 reviews, 1 bed, 1 bathroom
1–6 Aug
Superhost
Room in Upper Prince's Quarter
Panorama SXM - 1 BR Ocean View - Luxury Apartment
5.0 out of 5 average rating, 4 reviews, 1 king bed, 1.5 bathrooms
2–7 Aug
Top guest favourite
Flat in Simpson Bay
The Pineapple Suite
4.95 out of 5 average rating, 44 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Apartment in Simpson Bay
SkyPort Condo
4.98 out of 5 average rating, 81 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Sept
Top guest favourite
Flat in Cupecoy
Stunning oceanfront condo
4.97 out of 5 average rating, 36 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
12–17 Sept
Guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
4.96 out of 5 average rating, 107 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
1–6 Oct
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
4.99 out of 5 average rating, 98 reviews, 2 bedrooms, 4 beds, 2 bathrooms
8–13 Sept