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Search results; Over 1,000 homes in Simpson Bay

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Top guest favourite
Apartment in Simpson Bay, Sint Maarten
On the Sea - Beachfront 3 bedroom on Simpson Bay
3 bedrooms, 3 beds, 3 private bathrooms
1–6 Oct
,
4.92 out of 5 average rating, 26 reviews
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Guest favourite
Apartment in Simpson Bay, Sint Maarten
Hamaka condo, a beachfront retreat on Simpson Bay
Business host
25–30 Sept
4.95 out of 5 average rating, 106 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
The Loft at Simpson Bay Yacht Club
2 beds, 1.5 bathrooms
8–13 Dec
5.0 out of 5 average rating, 84 reviews
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Top guest favourite
Room in Simpson Bay, Sint Maarten
Sanctuary near Maho: Tropical beach vacation stay!
Individual host
1–6 Oct
5.0 out of 5 average rating, 9 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 69 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
Unit 1 - Apartment by the sea
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.94 out of 5 average rating, 32 reviews
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Top guest favourite
Villa in Simpson Bay, Sint Maarten
Surfsong Villa- Luxury Water Front Villa for 12
Business host
20–25 Sept
4.98 out of 5 average rating, 95 reviews
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Top guest favourite
Apartment in Simpson Bay, Sint Maarten
4 Bedroom Beachfront Condo with Private Pool D2.1
Individual host
20–25 Sept
4.97 out of 5 average rating, 29 reviews
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Top guest favourite
Loft in Marigot, St Martin
Sea Loft, Breathtaking View – Private Pool
2 bedrooms, 2 beds, 2 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 202 reviews
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Top guest favourite
Apartment in Simpson Bay, Sint Maarten
The Beach Condo
2 bedrooms, 2 king beds, 2.5 bathrooms
19–24 Sept
4.99 out of 5 average rating, 83 reviews
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Guest favourite
Villa in Simpson Bay, Sint Maarten
Beachfront 5BR Villa Impala w/ pool, Saint Maarten
5 bedrooms, 5 beds, 5.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 29 reviews
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Top guest favourite
Flat in Simpson Bay, Sint Maarten
TropiCasa - Watch sunsets surf the waves, 1BR
1 bedroom, 1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 16 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
Unit 7 - Luxury apartment by the sea
1 bedroom, 1 king bed, 1 bathroom
19–24 Sept
4.93 out of 5 average rating, 80 reviews
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Top guest favourite
Flat in Simpson Bay, Sint Maarten
Apartment on the beach 2
Individual host
30 Sept – 5 Oct
4.86 out of 5 average rating, 208 reviews
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Guest favourite
Flat in Simpson Bay, Sint Maarten
2BR Escape - Walk to Maho and Simpson Bay Beach
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
4.9 out of 5 average rating, 31 reviews
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Guest favourite
Flat in Lowlands, Sint Maarten
Luxury Maho Studio|Walk to Beach|5 mins to Airport
1 bedroom, 1 queen bed, 1 bathroom
23–28 Sept
4.92 out of 5 average rating, 12 reviews
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Guest favourite
Hotel room in Simpson Bay, Sint Maarten
Azure Hotel Bay Suite
1 bedroom, 1 single bed, 1 bathroom
31 Oct – 5 Nov
4.87 out of 5 average rating, 275 reviews
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Top guest favourite
Hotel in Upper Prince's Quarter, Sint Maarten
1BR Luxury Apartment | Ocean View
1 bedroom, 1 king bed, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Cole Bay, Sint Maarten
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 61 reviews