Beachfront vacation rentals in Simpson Bay
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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
Cottage in Cul-de-Sac, St. Martin
4.98 out of 5 average rating, 101 reviewsVILLA JADE 2: WATERFRONT/ POOL
Oct 29 – Nov 5
Condo in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 56 reviewsBeach front luxury! Huge 2BR that has it all! 😍🤩😍
Oct 28 – Nov 4
Condo in Lowlands
4.94 out of 5 average rating, 88 reviewsSint Maarten La Terrasse Maho
Apr 9 – 16
Apartment in Lowlands, Sint Maarten
4.94 out of 5 average rating, 17 reviewsA Maho Studio
Jun 8 – 15
Condo in Lowlands, Sint Maarten
4.88 out of 5 average rating, 16 reviewsHavya Cozy Stays
May 29 – Jun 5
Apartment in Cupecoy
5.0 out of 5 average rating, 6 reviewsBright Studio by Mullet Beach
Jul 12 – 19
Condo in Simpson Bay, Sint Maarten
5.0 out of 5 average rating, 29 reviewsEncanto -2BR beachfront w/pool & gorgeous sunsets!
Nov 21 – 28
Apartment in Lowlands, Sint Maarten
5.0 out of 5 average rating, 16 reviewsRock Star Gem in Maho
Jun 28 – Jul 5
Beachfront home rentals with a hot tub
Apartment in Cole Bay, Sint Maarten
5.0 out of 5 average rating, 4 reviewsA103 - Incredible Apartment with Garden
Jan 29 – Feb 5
Condo in Simpson Bay, Sint Maarten
4.9 out of 5 average rating, 10 reviewsLovely Lagoon Townhouse SBYC
Oct 2 – 9
Apartment in Simpson Bay, Sint Maarten
4.96 out of 5 average rating, 93 reviewsTop of the art penthouse
Jan 15 – 22
Home in Lowlands, Sint Maarten
4.9 out of 5 average rating, 69 reviewsSapphire Fantasy : Oceanfront paradise
Oct 20 – 27
Home in Cole Bay, Sint Maarten
4.89 out of 5 average rating, 38 reviewsSaint-Tropez With Ocean View - Boat Charter
Sep 27 – Oct 4
Villa in Little Bay, Sint Maarten
5.0 out of 5 average rating, 17 reviewsBarefoot Villas
Aug 6 – 13
Apartment in Lowlands, Sint Maarten
5.0 out of 5 average rating, 5 reviews1 bedroom paradise
Sep 22 – 29
Condo in Lowlands, Sint Maarten
5.0 out of 5 average rating, 27 reviewsThe Cliff in Cupecoy Beach HEAVEN!!!
Oct 22 – 29
Pet-friendly beachfront home rentals
Apartment in Lowlands, Sint Maarten
4.97 out of 5 average rating, 113 reviewsCupecoy Côté Jardin
Nov 7 – 14
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
Sep 27 – Oct 4
Apartment in Pelican Key, Sint Maarten
4.83 out of 5 average rating, 29 reviewsGated Oasis in Pelican Key
Aug 19 – 26
Apartment in Simpson Bay, Sint Maarten
4.89 out of 5 average rating, 46 reviewsSimpson Bay apartment-free parking, great location
Nov 27 – Dec 4
Home in Collectivité de Saint-Martin, St. Martin
4.88 out of 5 average rating, 32 reviewsNew "Salty Beach" 1 bdr beachfront
Sep 7 – 14
Townhouse in Cole Bay, Sint Maarten
5.0 out of 5 average rating, 72 reviewsHillside Beach Townhouse Simpson Bay
Sep 14 – 21
Condo in Collectivity of Saint Martin, St. Martin
4.89 out of 5 average rating, 37 reviewsApartment Canelle
Feb 2 – 9
Home in Simpson Bay
4.89 out of 5 average rating, 9 reviewsCoco's Beach House - Simpson Bay Beach
Jun 29 – Jul 6
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
€ 75 before taxes and fees
Destinations to explore
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- Rentals with a hot tub Simpson Bay
- Rentals with pools Simpson Bay
- Rentals with a washer and dryer Simpson Bay
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