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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Apartment in Simpson Bay
The Beach Condo
2 bedrooms, 2 beds, 2.5 private bathrooms
15–20 Aug
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4.99 out of 5 average rating, 79 reviews
Top guest favourite
Flat in Simpson Bay
Villa Harmony Haven
5.0 out of 5 average rating, 65 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
20–25 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
Top guest favourite
Flat in Simpson Bay
The Beach House Apartment
5.0 out of 5 average rating, 247 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
13–18 Jul
Guest favourite
Hotel room in Simpson Bay
Azure Hotel Bay Suite
4.87 out of 5 average rating, 262 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Aug
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Penthouse - Unit 3
5.0 out of 5 average rating, 40 reviews, 3 bedrooms, 3 beds, 3.5 bathrooms
18–23 Sept
Guest favourite
Flat in Maho Beach
Escapes at the Emerald – Airport & Beach Nearby
4.89 out of 5 average rating, 18 reviews, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Flat in Simpson Bay
Apartment on the beach 2
4.85 out of 5 average rating, 201 reviews, 1 bedroom, 1 bed, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Flat in Simpson Bay
SeaPearl 3Brm Beachfront Penthouse with Generator
4.9 out of 5 average rating, 51 reviews, 3 bedrooms, 3 beds, 3 bathrooms
2–7 Aug
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
5–10 Oct
Top guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
4.97 out of 5 average rating, 106 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
16–21 Oct
Guest favourite
Flat in Simpson Bay
Top of the art penthouse
4.95 out of 5 average rating, 111 reviews, 3 bedrooms, 4 beds, 3.5 bathrooms
1–6 Aug
Guest favourite
Apartment in Simpson Bay
1 Bedroom Seafront Flat D3
5.0 out of 5 average rating, 15 reviews, 1 bedroom, 1 bed, 1 bathroom
14–19 Jul
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
5.0 out of 5 average rating, 55 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Sept
Top guest favourite
Flat in Simpson Bay
Lilly's Beach
4.95 out of 5 average rating, 236 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Aug
Top guest favourite
Apartment in Simpson Bay
SkyPort Condo
4.97 out of 5 average rating, 79 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
16–21 Jul
Flat in Simpson Bay
Paradise by the Sea
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
20–25 Jul
Top guest favourite
Apartment in Lowlands
Maho 1 Bed Condo with ocean view & Free Wi-Fi
4.9 out of 5 average rating, 52 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept