Holiday rentals in Simpson Bay

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Top-rated holiday rentals in Simpson Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Guest house in Simpson Bay, Sint Maarten
White Sands Beach Studio
This is the studio apartment you want. In a prime location in a safe neighborhood, with everything need to enjoy a perfect vacation. You have supermarkets, car rentals, restaurants, and bars within walking distance. A 30-second walk from Simpson Bay beach &6 min to Maho Beach, our world-famous airport beach. Public transportation is also available there. The apartment is recently renovated and equipped with AC, Netflix, a cozy kitchen, a magnificent garden, and a terrace overlooking the airport.
15–22 Jul
$126 SGD per night
4.93 out of 5 average rating, 54 reviews
Guest favourite
Apartment in Simpson Bay
Beach front luxury! Huge 2BR that has it all! 😍🤩😍
5 star hotel luxury is yours in this modern beach home! 2 guest rooms with en-suite bathrooms and deck access. Enjoy cooking your own meals and dine inside or on the deck (or beach!). Largest deck on Simpson Bay beach has it all: huge daybed, loungers, living and dining areas for your comfort and pleasure. Unwind in the den and enjoy the big screen there or in either bedroom. Your neighbor is a boutique hotel and will gladly serve you meals and drinks right to your deck! Much more info available
20–27 Jan
$940 SGD per night
5.0 out of 5 average rating, 53 reviews
Guest favourite
Apartment in Simpson Bay
OCEAN FRONT Steps From BEACH!
Step into our oceanfront paradise on Simpson Bay beach. Just steps away from the sandy coast! Cherish sunrise serenity and late-night tranquility. Relax on the patio, absorb vistas, let waves weave their soothing symphony – a cherished moment! : ) Great location too! Close to Sunset Beach Bar—grab an ice-cold Heineken, watch planes land above. Famous Maho is also a quick stroll (5min from Sunset Bar). food, shops, nightlife, casinos its all there. A perfect location to properly discover SXM!
20–27 Oct
$323 SGD per night
5.0 out of 5 average rating, 26 reviews

Popular amenities for Simpson Bay holiday rentals

Stay near Simpson Bay's top sights

Simpson Bay Yacht Club6 locals recommend
Mary's Boon Beach Resort & Spa8 locals recommend
Kim Sha Beach10 locals recommend
Casino Royale15 locals recommend
Sunset Bar and Grill29 locals recommend
Sonesta Maho Beach Resort, Casino & Spa6 locals recommend

Other great holiday rentals in Simpson Bay

Guest favourite
Villa in Simpson Bay, Sint Maarten
Waterfront "BONJOUR" Beacon Hill St Maarten
8–15 Jun
$1,017 SGD per night
4.98 out of 5 average rating, 40 reviews
Guest favourite
Apartment in Simpson Bay
Beachside Escape
6–13 Sep
$468 SGD per night
5.0 out of 5 average rating, 15 reviews
Guest favourite
Flat in Simpson Bay
Vista Blue-Newly Renovated
3–10 Oct
$542 SGD per night
5.0 out of 5 average rating, 11 reviews
Guest favourite
Apartment in Simpson Bay, Sint Maarten
Beachfront 2 BDR modern condo
11–18 Jul
$368 SGD per night
5.0 out of 5 average rating, 20 reviews
Guest favourite
Apartment in Simpson Bay
Five Star Luxury Beachfront Condo Private Hot Tub
20–27 Sep
$544 SGD per night
4.96 out of 5 average rating, 71 reviews
Guest favourite
Flat in Simpson Bay
HARMONY HAVEN on Simpson Bay Beach Beacon Hill
7–14 Feb
$1,144 SGD per night
5.0 out of 5 average rating, 45 reviews
Guest favourite
Apartment in Simpson Bay
Beachfront Caribbean Breeze in Paradise, SXM
2–9 Nov
$431 SGD per night
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Simpson Bay
NEW Double S Suite
6–13 Nov
$137 SGD per night
4.84 out of 5 average rating, 19 reviews
Guest favourite
Apartment in Simpson Bay, Sint Maarten
Encanto -2BR beachfront w/pool & gorgeous sunsets!
7–14 Nov
$414 SGD per night
5.0 out of 5 average rating, 27 reviews
Guest favourite
Serviced apartment in Simpson Bay
CocoVaa Boutique Beach Hotel - Diamond Suite
8–15 Oct
$368 SGD per night
4.92 out of 5 average rating, 12 reviews
Guest favourite
Guest house in Simpson Bay
Simpson Bay Beach Apartment. Topdeck. Ocean View
24–31 Jan
$227 SGD per night
4.96 out of 5 average rating, 96 reviews
Guest favourite
Apartment in Simpson Bay, Sint Maarten
Hamaka condo, a beachfront retreat on Simpson Bay
26 Jan – 2 Feb
$379 SGD per night
4.97 out of 5 average rating, 33 reviews

Quick stats about holiday rentals in Simpson Bay

Total rentals

330 properties

Rentals with a pool

210 properties have a pool

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

140 properties are a good fit for families

Total number of reviews

7.5K reviews

Nightly prices starting at

$40 SGD before taxes and fees

Destinations to explore