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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Flat in Simpson Bay
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 private bathroom
12–17 Oct
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4.94 out of 5 average rating, 32 reviews
Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
3 bedrooms, 3 queen beds, 3 bathrooms
13–18 Sept
4.91 out of 5 average rating, 58 reviews
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 84 reviews
Guest favourite
Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
13–18 Sept
4.87 out of 5 average rating, 275 reviews
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.99 out of 5 average rating, 105 reviews
Superhost
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.87 out of 5 average rating, 142 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
Top guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
Individual host
13–18 Sept
4.97 out of 5 average rating, 29 reviews
Guest favourite
Villa in Simpson Bay
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds, 5.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Room in Simpson Bay
Sanctuary near Maho: Tropical beach vacation stay!
Individual host
1–6 Oct
5.0 out of 5 average rating, 9 reviews
Guest favourite
Flat in Maho Beach
Escapes at the Emerald – Airport & Beach Nearby
Individual host
16–21 Nov
4.93 out of 5 average rating, 27 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
10–15 Mar
4.96 out of 5 average rating, 109 reviews
Townhouse in Simpson Bay
The Drake’s "Suite Serenity" @ White Sands Villas
3 bedrooms, 6 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Apartment in Simpson Bay
Maho Beach Oceanfront Getaway
1 bedroom, 2 beds, 1 bathroom
28 Sept – 3 Oct
4.67 out of 5 average rating, 230 reviews
Guest favourite
Flat in Cole Bay
C354 - Top view with balcony
1 bedroom, 1 king bed, 1 bathroom
15–20 Oct
4.95 out of 5 average rating, 21 reviews
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 60 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 Lowlands
Luxury Maho Studio|Walk to Beach|5 mins to Airport
1 bedroom, 1 queen bed, 1 bathroom
23–28 Sept
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Flat in Simpson Bay
Stunning Boho-Chic Beach Condo with Rooftop
2 bedrooms, 2 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 16 reviews