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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Apartment in Simpson Bay
CasaPisani Tranquil 2Bed condo SimpsonBayYachtClub
2 bedrooms, 2 beds, 2 private bathrooms
11–16 Sept
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4.96 out of 5 average rating, 55 reviews
Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
5–10 Sept
5.0 out of 5 average rating, 69 reviews
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
4–9 Sept
5.0 out of 5 average rating, 82 reviews
Guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds, 4 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 27 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, 29 reviews
Guest favourite
Flat in Simpson Bay
Private Pool- 5 min DRIVE to Maho Beach & Airport
1 bedroom, 1 queen bed, 1 bathroom
17–22 Sept
4.96 out of 5 average rating, 76 reviews
Guest favourite
Apartment in Simpson Bay
SeaViews 2Brm Ocean Front Condo SXM
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.91 out of 5 average rating, 35 reviews
Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
7–12 Sept
4.91 out of 5 average rating, 57 reviews
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 60 reviews
Guest favourite
Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
24–29 Sept
4.87 out of 5 average rating, 272 reviews
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
6–11 Sept
4.99 out of 5 average rating, 104 reviews
Top guest favourite
Serviced apartment in Simpson Bay
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 bathroom
4–9 Sept
4.94 out of 5 average rating, 32 reviews
Guest favourite
Room in Upper Prince's Quarter
1BR Luxury Apartment | Ocean View
1 king bed, 1.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 19 reviews
Guest favourite
Flat in Maho Beach
Escapes at the Emerald – Airport & Beach Nearby
1 queen bed, 1 bathroom
16–21 Nov
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Apartment in Simpson Bay
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 king beds, 3 bathrooms
1–6 Oct
4.92 out of 5 average rating, 26 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
Guest favourite
Villa in Indigo Bay
Villa Ocean - Indulge Yourself in Paradise
3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
4.95 out of 5 average rating, 81 reviews
Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
2 bedrooms, 2 king beds, 2.5 bathrooms
16–21 Oct
4.96 out of 5 average rating, 109 reviews
Top guest favourite
Flat in Cupecoy
Stunning oceanfront condo
2 bedrooms, 2 king beds, 2.5 bathrooms
15–20 Sept
4.98 out of 5 average rating, 40 reviews