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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
,
4.97 out of 5 average rating, 106 reviews
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
6–11 Jul
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
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
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
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
23–28 Jul
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
Hotel room in Simpson Bay
Azure Hotel Bay Suite
4.86 out of 5 average rating, 259 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Aug
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
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
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
4.9 out of 5 average rating, 50 reviews, 3 bedrooms, 3 beds, 3 bathrooms
2–7 Aug
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
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
Guest favourite
Villa in Simpson Bay
Waterfront "Bonjour" Beacon Hill St Maarten
4.97 out of 5 average rating, 86 reviews, 4 bedrooms, 4 beds, 4 bathrooms
7–12 Jul
Top guest favourite
Flat in Simpson Bay
Lilly's Beach
4.95 out of 5 average rating, 234 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Aug
Top guest favourite
Flat in Cole Bay
Beautiful, bright apartment with a lagoon view in Simpson Bay
5.0 out of 5 average rating, 14 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Aug
Top guest favourite
Apartment in Simpson Bay
SkyPort Condo
4.97 out of 5 average rating, 79 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Jul
Top guest favourite
Apartment in Simpson Bay
CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
4.98 out of 5 average rating, 50 reviews, 2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug