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Search results; Over 1,000 homes in Simpson Bay

Top guest favourite
Guest house in Simpson Bay
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 bed, 1 private bathroom
9–14 Sept
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4.95 out of 5 average rating, 109 reviews
Guest favourite
Flat in Simpson Bay
Villa Harmony Haven
3 bedrooms, 3 king beds, 3.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 69 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
Top guest favourite
Apartment in Simpson Bay
Popular Beachfront Property Barefoot /Simpson bay
2 bedrooms, 2 king beds, 2.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 27 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
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
Top guest favourite
Villa in Cole Bay
[Sunset Place] 3BR Oceanfront Villa, Private Pool
3 bedrooms, 3 beds, 3 bathrooms
3–8 Oct
5.0 out of 5 average rating, 14 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
Home in Koolbaai
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds, 2.5 bathrooms
18–23 Sept
New place to stay
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
Guest favourite
Villa in Cole Bay
Pelican Key*Amazing VIEWS! Private Pool *
5 bedrooms, 5 beds, 4 bathrooms
9–14 Sept
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Villa in Little Bay
Barefoot Villas GreatBay View in Hot Tub & Balcony
2 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
4.99 out of 5 average rating, 105 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, 47 reviews
Guest favourite
Villa in Koolbaai
Villa Livity 6 Bed Luxury Sea view boutique villa
Business host
10–15 Sept
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Home in Cole Bay
Puerta Al Mar - Ocean-Side Villa Tranquility
5 bedrooms, 5 beds, 5.5 bathrooms
12–17 Oct
4.98 out of 5 average rating, 53 reviews
Guest favourite
Apartment in Simpson Bay
Beachfront Paradise with Pool & Stunning Sunsets
2 bedrooms, 3 beds, 2 bathrooms
28 Oct – 4 Nov
4.9 out of 5 average rating, 72 reviews
Top guest favourite
Flat in Simpson Bay
Simpson bay beach, spacious, beautiful views!
3 bedrooms, 3 king beds, 2 bathrooms
10–15 Sept
5.0 out of 5 average rating, 157 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
Top guest favourite
Villa in Simpson Bay
Surfsong Villa- Luxury Water Front Villa for 12
6 bedrooms, 6 king beds, 6 bathrooms
20–25 Sept
4.98 out of 5 average rating, 95 reviews