Holiday rentals in Simpson Bay

Guest house in Simpson Bay

4.91 out of 5 average rating, 108 reviews

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.

4.86 out of 5 average rating, 43 reviews

NEW Double S Suite

In the heart of Simpsonbay, close to bars, restaurants, and the beach, you'll find this stylish and newly constructed apartment. Only 4 min from the airport and have double-paned windows to keep out the noise. The apartment has a queen-size bed, free Wi-Fi, and 2 flat-screen TVs; it's also only 2 minutes from Simpson bay beach, known for its clear water. This chic grey and white studio comes with all the amenities necessary for a restful and romantic beach getaway in the middle of St. Maarten.

5 out of 5 average rating, 43 reviews

The Loft at Simpson Bay Yacht Club

Welcome to The Loft at SBYC. Located in the heart of Simpson Bay in walking distance to the beach, great restaurants, grocery stores, shopping, salons/spas and more. In this fully renovated loft-style apartment, you will find high quality amenities throughout including a European kitchen and an amazing rainfall shower. The SBYC property offers 3 swimming pools, a hot tub, tennis courts and plenty of outdoor space for relaxing, all under 24-hour gated security. Free concierge service included.

4.87 out of 5 average rating, 207 reviews

Apartment on the beach

Let this tranquil, centrally located, 1 bedroom apartment become your home away from home. This beachfront property is located on the BEST and WIDEST stretch of Simpson Bay beach with gentle waves and no rocks, which makes it a perfect spot for swimming. Although this property is tucked away, and there are never many people on this part of the beach, it is in a heart of Simposn Bay. Simpson Bay beach offers one of the longest stretches of uninterrupted sandy, white coastline on Sint Maarten.

4.91 out of 5 average rating, 110 reviews

Apartment in Lowlands

Modern Oceanview 2-Bedroom Condo on Mullet Bay

Welcome to Fourteen, one of the most luxurious beachfront residences in St Maarten located directly on the famous Mullet Bay beach and golf course. Located on the 9th floor, You will find this spacious 2 bedroom condo offering beautiful ocean views, great for a group, family, or romantic getaway. Indulge yourself in all of the amenities, outstanding concierge services and dining experience Fourteen has to offer. We aim to make your stay unforgettable. $5 per night resort fee not included

4.96 out of 5 average rating, 197 reviews

Lilly's Beach

This is a very SPECIAL SMAll RESIDENCE known as Ocean Edge . Beach Front located directly on beautiful Simpson Bay Beach! Enjoys one of the best locations on the island . Panoramic sea views with your toes in the sand and balmy Caribbean breezes. A clear turquoise sea dazzles in tropical sun, powdery white sands stretching along one of St. Maarten's longest beaches. Apartment with modern amenities and comforts. A perfect vacation spot ! Back up system installed to insure electricity.

4.92 out of 5 average rating, 62 reviews

Flat in Maho Beach

Turtle Den YOUR Maho Escape!

Welcome to Turtle Den, an enchanting ocean-inspired studio in the heart of Maho, St. Maarten. More than a stay, it's an immersive experience. Dive into a tranquil palette of oceanic hues, playful turtle motifs, and serene vibes. Just steps from Maho Beach, where planes land and take off, it's a front-row seat to breathtaking moments. Immerse in Maho's lively scene, surrounded by clubs and restaurants. Turtle Den is an invitation to savor the ocean's beauty and celebrate a world of whimsy.

5 out of 5 average rating, 205 reviews

The Beach House Apartment

A stylishly modern one bedroom apartment directly located on the beautiful white sand beach of Simpson Bay. Enjoy the crystal clear waters by day and explore the Caribbean charm of our bustling nightlife. Our island getaway provides you with the full relaxation experience complete with beach chairs, umbrellas, outdoor shower, snorkel gear and paddle boards to complete beach side experience Amenities include free WIFI, kitchen, king size bed, beach chairs, umbrella's and much more

4.93 out of 5 average rating, 122 reviews

Le Petit Paradis – Beachfront 1 Bedroom Apartment

"Petit Paradis" (Little Paradise), a genuine Caribbean getaway. A spacious one-bedroom Beachfront apartment right on beautiful Simpson Bay Beach and in the center of all the happenings. Relaxing terrace, five stairs away from the Beach, and within walking distance from great Restaurants, Nightlife, Activities, and Watersports. This modern, fully furnished, and equipped apartment has everything you need for a dream vacation, Hope to invite you soon in our Paradise, Elodie

5 out of 5 average rating, 12 reviews

Condo in Simpson Bay

Location, Location, Location!! This delightful, newly renovated, centrally located Simpson Bay Yacht Club condo is yours to enjoy. A welcoming spacious one bedroom +Queen Sofa bed in living room. Private patio overlooking the lagoon. Two communal swimming pools / two tennis courts . 24-hour security for peace of mind. New A/C. Two designated parking spaces. Short walking distance to the beach, cafe's, supermarket, restaurant, bars and cinema.

4.99 out of 5 average rating, 81 reviews

SECOND HOME Beach Apartment

Our SECOND HOME beach apartment is truly designed as a second home. A place to where we can escape from the world and reconnect with ourselves. It has all the amenities one needs, like a comfortable living room, high quality mattress and linens, cozy sitting on the terrace to watch the sunset, fully equipped kitchen, and airconditioning in each room. It is located just two houses away from the beautiful white sand beach of Simpson Bay.

Guest suite in Simpson Bay

4.82 out of 5 average rating, 212 reviews

MYRIEL — Perfect Location/Nightlife/Beach

This Duplex 1 Bed apt is all about LOCATION. Nicest/Safest area of St.Maarten. Few steps from Simpson beach, Maho Beach nightlife/restaurants. 5-10mn walk on the beach to Karakter Beach bar and Sunset Beach Café. Very clean. Perfect for single or couple. Sleep up to 3 with sofa bed.. Private entrance, full kitchen, Stove, Microwave, A/C, WIFI, Linens and towels.

Holiday rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Houses

A space that's all yours, with room for everyone

Flats

Convenient locations with everyday essentials

Popular amenities for Simpson Bay holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Simpson Bay

5 out of 5 average rating, 34 reviews

Le Papillon -Modern, beachfront, 550sq. ft terrace

LaurieRating, 5 stars1 month ago

Beachfront. Need I say more? We loved seeing the ocean, hearing the waves crash, and walking the beach every day. This was, by far, the best Airbnb we ever stayed at. It is close to the airport (so you can get your vacation started sooner) and walkable to restaurants and bars. It has secured, dedicated parking. It was organized, clean, well-stocked. The Host, Simona, is responsive, thoughtful, and professional. We highly recommend and will definitely return!

Home in Indigo Bay

4.77 out of 5 average rating, 155 reviews

La Pearle - Luxurious 1 Bedroom Condo By the Beach

MakiahRating, 5 stars5 days ago

This place was absolutely beautiful! It looked exactly like the pictures! I loved how responsive the host was during my stay! I would definitely stay again!

4.84 out of 5 average rating, 75 reviews

Flat in Lowlands

Modern Studio in gated Resort pool & gym.generator

LydiaRating, 5 stars1 month ago

Our stay at Ricardo's was absolutely amazing. The location is unbeatable, just steps away from the famous Maho Beach where you can watch planes land up close ✈️, and also super close to the airport and all the local hotspots, restaurants, shops. The apartment was spotless, beautifully maintained, and smelled amazing the moment we walked in. The bedding was extremely comfortable, the kitchen was well stocked and every detail was thoughtfully arranged for a relaxing and enjoyable stay. Although the standard arrival time was after 4:00 pm, we were generously offered an earlier slot at 1:00 pm. The self check-in process was a breeeze. Everything went smoothly, and departure was just as easy. A lovely bonus was the complimentary bottled water in the fridge, which was much appreciated. Whether you’re looking to explore the island or unwind in a clean, cozy, and well-located home base, this spot is perfect. 👏 We highly recommend this five stars listing! Thanks for hosting us Ricardo! 🙏

5 out of 5 average rating, 13 reviews

Flat in Marigot

Studio Coconut

Esther-JoyRating, 5 stars3 weeks ago

If you’re looking for a quiet place to relax and unwind this place is for you. It’s on a beach but the waters weren’t so calm so I didn’t want to take the chance. Lola is very hospitable & was very responsive and helpful before and after arriving. The studio is just as seen in photos, very clean and has a modern cozy vibe. I’d suggest you rent a car…Lola helped with that before I arrived so I was able to pick up the car at the airport. I think this is a great option for a solo traveler as well.

4.96 out of 5 average rating, 23 reviews

Flat in Lowlands

Villa Spice For Life SXM 2

MauritsRating, 5 stars1 month ago

A hidden gem! Everything was curated with care! From the crisp linens to the warm welcome. Left with great memories!

4.92 out of 5 average rating, 36 reviews

Flat in Cole Bay

Beautiful Spacious Studio with spectacular view

IdaRating, 5 stars1 week ago

Had a wonderful time at Rosyenni, the apartment got everything you needed, Eventually you need to rent a car as the location is a little far by walking distance from the village Pelican Bay, and Simpson Bay, plus the view from the balcony is breath taken, you can chill at night watching the boat traffic, will recommend it 100%🙏😃

Townhouse in Sint Maarten

5 out of 5 average rating, 74 reviews

Indigo Bay Villa Poolside - Ocean 14

WendyRating, 5 stars2 months ago

Wonderful rental the reviews are correct so nice to come home after being at the beach and have your own pool and space to hang out. I think they thought of just about everything thank you Franklin. He was such a Gem Every little thing he would pop right over and take care of even when there were things that we thought were broken or not working but evidently were 🤷‍♀️ lol. Would definitely stay again.