Beachfront vacation rentals in Simpson Bay
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Simpson Bay
Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Simpson Bay beachfront rentals
Beachfront home rentals with a pool
Villa in Cul-de-Sac, St. Martin
4.98 out of 5 average rating, 101 reviewsVILLA JADE 2: WATERFRONT/ POOL
Oct 21 – 28
Apartment in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 3 reviewsThe Loft at Simpson Bay Yacht Club
Aug 14 – 21
Condo in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 29 reviewsEncanto -2BR beachfront w/pool & gorgeous sunsets!
Dec 16 – 23
Condo in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 16 reviewsBeachfront Caribbean Breeze in Paradise, SXM
Sep 5 – 12
Condo in Simpson Bay
4.96 out of 5 average rating, 72 reviewsFive Star Luxury Beachfront Condo Private Hot Tub
Oct 17 – 24
Apartment in Lowlands, Sint Maarten
4.94 out of 5 average rating, 17 reviewsA Maho Studio
Jun 8 – 15
Apartment in Lowlands, Sint Maarten
5.0 out of 5 average rating, 17 reviewsRock Star Gem in Maho
Aug 11 – 18
Apartment in Lowlands, Sint Maarten
5.0 out of 5 average rating, 9 reviewsEmerald Apt at Maho Beach
Nov 10 – 17
Beachfront home rentals with a hot tub
Guest suite in Cole Bay
4.94 out of 5 average rating, 160 reviewsIndigo Sweet
Jan 11 – 18
Apartment in Cole Bay, Sint Maarten
5.0 out of 5 average rating, 4 reviewsA103 - Incredible Apartment with Garden
Jul 15 – 22
Condo in Simpson Bay, Sint Maarten
4.9 out of 5 average rating, 10 reviewsLovely Lagoon Townhouse SBYC
Sep 24 – Oct 1
Apartment in Simpson Bay, Sint Maarten
4.96 out of 5 average rating, 93 reviewsTop of the art penthouse
Aug 9 – 16
Home in Lowlands, Sint Maarten
4.9 out of 5 average rating, 69 reviewsSapphire Fantasy : Oceanfront paradise
Mar 9 – 16
Apartment in Lowlands, Sint Maarten
5.0 out of 5 average rating, 5 reviews1 bedroom paradise
May 15 – 22
Condo in Lowlands, Sint Maarten
5.0 out of 5 average rating, 27 reviewsThe Cliff in Cupecoy Beach HEAVEN!!!
Aug 13 – 20
Villa in Little Bay, Sint Maarten
5.0 out of 5 average rating, 17 reviewsBarefoot Villas
Nov 3 – 10
Pet-friendly beachfront home rentals
Apartment in Lowlands, Sint Maarten
4.97 out of 5 average rating, 113 reviewsCupecoy Côté Jardin
Nov 4 – 11
Condo in Saint Martin , St. Martin
4.86 out of 5 average rating, 109 reviews2 Bedroom Duplex up to 5 guests right on the beach
Oct 3 – 10
Apartment in Simpson Bay, Sint Maarten
4.89 out of 5 average rating, 47 reviewsSimpson Bay apartment-free parking, great location
Oct 31 – Nov 7
Townhouse in Cole Bay, Sint Maarten
5.0 out of 5 average rating, 72 reviewsHillside Beach Townhouse Simpson Bay
Sep 8 – 15
Condo in Collectivity of Saint Martin, St. Martin
4.89 out of 5 average rating, 37 reviewsApartment Canelle
May 19 – 26
Apartment in Pelican Key, Sint Maarten
4.84 out of 5 average rating, 31 reviewsGated Oasis in Pelican Key
Nov 3 – 10
Home in Collectivité de Saint-Martin, St. Martin
4.88 out of 5 average rating, 32 reviews"Salty Beach" - Amazing 1 bedroom beachfront
Sep 20 – 27
Condo in Lowlands, Sint Maarten
4.97 out of 5 average rating, 33 reviewsGorgeous Beachfront PENTHOUSE- Sunset Ocean Views!
Jul 10 – 17
Quick stats about beachfront rentals in Simpson Bay
Total rentals
110 properties
Rentals with a pool
80 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
5K reviews
Nightly prices starting at
$80 before taxes and fees
Destinations to explore
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- Rentals with a hot tub Simpson Bay
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- Rentals with pools Simpson Bay
- Villa rentals Simpson Bay
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- Monthly Rentals Simpson Bay
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