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Search results; Over 1,000 homes in Simpson Bay

Guest favourite
Serviced apartment in Simpson Bay
Unit 8 - Luxury apartment by the sea
1 bedroom, 1 bed, 1 private bathroom
31 Aug – 5 Sept
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4.93 out of 5 average rating, 135 reviews
Home in Koolbaai
A waterfront paradise facing the ocean on Saint Martin
4 bedrooms, 6 beds
18–23 Aug
New place to stay
Superhost
Apartment in Upper Prince's Quarter
Serenity Seascape | 2BR Retreat, 270° Oceanviews
2 bedrooms, 2 king beds
24–29 Aug
5.0 out of 5 average rating, 5 reviews
Townhouse in Simpson Bay
Utopia A3 | Beachside Stay @ The Drake Residences
2 bedrooms, 3 beds
18–23 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest house in Simpson Bay
Simpson Bay Beach 1 bed Apt Topdeck. Ocean views
1 bedroom, 1 queen bed
18–23 Aug
4.95 out of 5 average rating, 109 reviews
Top guest favourite
Villa in Sint Maarten
Indigo Oceanfront Condo Middle Floor - Unit 2
3 bedrooms, 3 beds
21–26 Aug
5.0 out of 5 average rating, 36 reviews
Guest favourite
Flat in Upper Prince's Quarter
Aman_Luna
2 bedrooms, 3 beds
1–6 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Villa in Cole Bay
[Sunset Place] 3BR Oceanfront Villa, Private Pool
3 bedrooms, 3 beds
3–8 Oct
5.0 out of 5 average rating, 13 reviews
Guest favourite
Flat in Simpson Bay
SeaBliss 3BR Palm Beach Condo Simpson Bay
3 bedrooms, 3 beds
18–23 Aug
4.98 out of 5 average rating, 40 reviews
Guest favourite
Home in Cole Bay
Spacious 3BR with Private Cozy Pool
3 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 59 reviews
Guest favourite
Flat in Simpson Bay
The Loft at Simpson Bay Yacht Club
2 beds
7–12 Sept
5.0 out of 5 average rating, 81 reviews
Guest favourite
Apartment in Simpson Bay
SeaShores Beach Front 1 Brm Apt With Generator SXM
1 bedroom, 2 beds
31 Aug – 5 Sept
4.95 out of 5 average rating, 57 reviews
Guest favourite
Apartment in Simpson Bay
4 Bedroom Beachfront Condo with Private Pool D2.1
4 bedrooms, 5 beds
6–11 Sept
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Villa in Indigo Bay
AZUR 4BR 4.5BA Walk to Indigo Beach- Sea Side Dr.
4 bedrooms, 4 king beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 15 reviews
Guest favourite
Flat in Maho Beach
Turtle Den YOUR Maho Escape!
1 bedroom, 1 bed
28 Sept – 3 Oct
4.88 out of 5 average rating, 139 reviews
Guest favourite
Apartment in Simpson Bay
SeaViews 2Brm Ocean Front Condo SXM
2 bedrooms, 2 beds
23–28 Aug
4.91 out of 5 average rating, 33 reviews
Home in Koolbaai
Villa Where Dreams Meet the Sea
2 bedrooms, 2 king beds
26–31 Aug
New place to stay
Guest favourite
Hotel room in Simpson Bay
Azure Hotel Bay Suite
1 bedroom, 1 single bed
7–12 Sept
4.87 out of 5 average rating, 268 reviews
Home in Lowlands
#1 Unique luxury villa, pool & stunning sea views
4 bedrooms, 5 beds
20–25 Aug