Holiday rentals in Simpson Bay

Guest house in Simpson Bay

4.9 out of 5 average rating, 109 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.

4.9 out of 5 average rating, 67 reviews

Apartment in Lowlands

Havya Cozy Stays

Keep it simple at this peaceful, well located studio unit at The Emerald at Maho with a common pool and gym. Just 5 minutes away from the International Airport, and walking distance from beaches with one being St. Maarten's famous end of the runway beach. Nowhere else in the world are you able to witness take-off and landing of Jumbo-jets as closely as here, all while sipping on a cocktail. Many shops stay open until 11pm, many bars, restaurants, nightclubs are all within easy walking distance.

4.86 out of 5 average rating, 44 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, 44 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.

4.91 out of 5 average rating, 111 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, 63 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, 206 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, 123 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

4.9 out of 5 average rating, 204 reviews

Apartment in Maho

Serene Oasis: Unwind by the Rooftop Pool & Hot Tub

This charming, cozy, and tranquil tropical nest is located where all the action is! The golf course, iconic bars, the unprecedented landing strip, the popular Maho and Mullet bay beaches, Maho market with daily fresh take away breakfast/lunch buffets and a divine selection of exotic restaurants are all in walking distance! If you wish to just lounge and relax by the pool, jacuzzi, and private gazebo bar or enjoy the nightlife; it’s all readily available, at your fingertips!

4.99 out of 5 average rating, 156 reviews

Loft in Marigot

Sea Loft, Breathtaking View – Private Pool

* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with lounge chairs, garden furniture, outdoor table and BBQ * Office area * 100 Mbps Wi-Fi * TV with thousands of channels from around the world * 250 m walk to Fort Louis de Marigot Marina * 5 min walk to Marigot city center with its restaurants, boutiques and other shops * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

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.

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Popular amenities for Simpson Bay holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Simpson Bay

Home in Indigo Bay

4.77 out of 5 average rating, 156 reviews

La Pearle - Luxurious 1 Bedroom Condo By the Beach

ShandraRating, 5 stars5 days ago

Le Pearle, is an amazing place to stay while in paradise. The location is private, the views are incredible, and you have the luxury of a beach at your disposable. The condo itself is very beautiful, the bed is comfortable, my boyfriend and I felt right at home and would highly recommend staying here.

5 out of 5 average rating, 14 reviews

Flat in Marigot

Studio Coconut

Esther-JoyRating, 5 stars1 month 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.

4.9 out of 5 average rating, 48 reviews

Apartment in Simpson Bay

Encanto -2BR Beachfront w/Pool & Gorgeous Sunsets!

TinaRating, 5 stars3 weeks ago

We enjoyed our stay at Encanto. Rakhi was a very informative and she responded quickly to any questions we had. Gordon, the property manager, gave us instructions on the unit when we arrived. Rakhi provided recommendations which were helpful. The condo was very spacious and the balcony was large with a beautiful view. Our favorite restaurant was Palapa which was within walking distance (we ate there twice). The breakfast at the Yellow Sub in Orient Beach was delicious - best croissants. Carrefour was a great place to get provisions for the week and were reasonably priced. Every place took American dollars but only a few took American Express. We highly recommend spending a day at Pinel Island - Karibuni has chairs, umbrellas and cold beer!! The UnderSXM snorkel tour was really interesting. We rented a car to explore the island and the drivers are crazy so be careful - lol.

4.75 out of 5 average rating, 60 reviews

Sunshine, Sea & Sand - Apt 3

NicolleRating, 5 stars5 months ago

The apartment and location far exceeded my expectations! Very close to shopping and restaurants as well as the beautiful beach! I will definitely stay here again!! 🌺

5 out of 5 average rating, 18 reviews

Apartment in Marigot

New studio with superb view of the Caribbean Sea

AbdoulayeRating, 5 stars1 week ago

Georgi was an amazing host, she was very communicative, helpful, and very accommodating . Her place was clean, modern, and has a great view of the beach. I would highly recommend booking her for your trips to the island.

5 out of 5 average rating, 28 reviews

Apartment in Simpson Bay

Beachfront Caribbean Breeze in Paradise, SXM

JasonRating, 5 stars1 month ago

all i can say is wow! what a great stay from helpful communication,to the location all of this was what we were looking for and we found that and more at Sylvia's wonderful place,thanks for having g us,and look forward to staying there again

5 out of 5 average rating, 7 reviews

Spacious Studio just minutes to the Beach

BrenyannaRating, 5 stars2 weeks ago

The place looked just the photos! It was a beautiful stay and the space looks larger in person compared to the photos. My husband and I stayed 8 days in the unit. The kitchen was packed with everything we needed, there were extra chargers and cables around the house which was helpful since we lost our charger at the airport. Beach chairs, towel, and umbrellas were all provided. A rental car place was within walking distance. They provided excellent recommendations for food and activities for places all around the island. 10/10 would absolutely recommend.