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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Villa in Simpson Bay
Waterfront "Bonjour" Beacon Hill St Maarten
4 bedrooms, 4 beds, 4 private bathrooms
18–23 Oct
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4.97 out of 5 average rating, 91 reviews
Top guest favourite
Apartment in Simpson Bay
Popular Beachfront Property Barefoot /Simpson bay
2 bedrooms, 2 king beds, 2.5 bathrooms
10–15 Sept
5.0 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
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool C2.1
Individual host
14–19 Sept
4.9 out of 5 average rating, 21 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
Guest favourite
Villa in Cole Bay
Pelican Key*Amazing VIEWS! Private Pool *
5 bedrooms, 5 beds, 4 bathrooms
10–15 Sept
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Apartment in Simpson Bay
The Penthouse at LaSiesta - 3 BD - Luxury Awaits!
3 bedrooms, 3 king beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
4.99 out of 5 average rating, 105 reviews
Home in Koolbaai
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds, 2.5 bathrooms
18–23 Sept
New place to stay
Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 69 reviews
Top guest favourite
Villa in Philipsburg
Villa Dream View Belair Sint Maarten SXM
3 bedrooms, 4 beds, 3 bathrooms
21–26 Nov
4.99 out of 5 average rating, 335 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
Flat in Simpson Bay
Simpson bay beach, spacious, beautiful views!
3 bedrooms, 3 king beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 157 reviews
Top guest favourite
Home in Koolbaai
Pelican key - BEACH FRONT Villa
Individual host
27 Sept – 2 Oct
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Flat in Simpson Bay
Stunning Boho-Chic Beach Condo with Rooftop
2 bedrooms, 2 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 16 reviews
Guest favourite
Villa in Koolbaai
Villa Livity 6 Bed Luxury Sea view boutique villa
Business host
11–16 Sept
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Middle Floor - Unit 2
3 bedrooms, 3 beds, 3.5 bathrooms
11–16 Sept
4.97 out of 5 average rating, 37 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
24–29 Apr
4.96 out of 5 average rating, 109 reviews
Superhost
Flat in Simpson Bay
Beachcomb Escape
1 bedroom, 2 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 10 reviews