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Vacation rentals in Simpson Bay

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Simpson Bay

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

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Superhost
A spacious terrace features a comfortable seating area with plush cushions. Lush greenery surrounds the space, offering a sense of tranquility. A staircase leads to an upper level. In the distance, a view of buildings and the sky is visible, enhancing the outdoor ambiance.
Guesthouse in Simpson Bay
4.87 out of 5 average rating, 121 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.

Guest favorite
A vibrant blue gate opens to reveal a sandy beach and calm waters. Decorative pots with blooming pink flowers frame the entrance, accompanied by lush green leaves. In the distance, sailboats can be seen on the horizon under a cloudy sky.
Apartment in Simpson Bay
4.88 out of 5 average rating, 223 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.

Top guest favorite
A serene beach view is captured, showcasing clear turquoise waters meeting powdery white sands. A picnic table sits on the beach, bordered by vibrant green plants and palm trees. Soft clouds drift above under a bright blue sky, completing the tranquil seaside scene.
Apartment in Simpson Bay
4.96 out of 5 average rating, 203 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.

Top guest favorite
Large glass sliding doors open to a sunny outdoor deck with views of the turquoise ocean. Comfortable lounge chairs and a dining table are visible among tropical palm trees. The living area features a soft gray couch and a wall-mounted TV, creating an inviting indoor space.
Apartment in Simpson Bay
5 out of 5 average rating, 221 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

Guest favorite
Apartment in Simpson Bay
4.93 out of 5 average rating, 135 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

Top guest favorite
A spacious dining area features a wooden table set with a bowl of oranges. Natural light streams through large windows, illuminating the cozy seating area in the background. Green plants add vibrancy to the room, creating a welcoming, serene atmosphere.
Apartment in Lowlands
4.97 out of 5 average rating, 137 reviews

Cupecoy Garden Side 1

Delightful one bedroom appt. Fully furnished with mid century teak furniture. A spacious 70m2 space with large terrace in a mature tropical garden. A brand new fully equipped kitchen was added in October 2022. Located in trendy and safe Cupecoy. CJ1 is a quiet oasis to relax in the luxurious garden, or head for the the renowned beach of Mullet bay within a 3 minute walk. Supermarkets, gym yoga studio very close by. This is the place to be.

Top guest favorite
A spacious terrace is presented with a wooden dining table surrounded by four chairs, complemented by a selection of fresh fruit. Sun loungers are positioned for relaxation, with a view of the turquoise water and sailboats visible in the distance.
Apartment in Simpson Bay
5 out of 5 average rating, 137 reviews

Simpson bay beach, spacious, beautiful views!

Amazing spacious 3 bedroom, 2 bathroom apartment with awesome location in the heart of Simpson Bay. location, location, location in the middle of it all. Right across the 2.5 mile beautiful Simpson Bay Beach. All the beach necessities are there to enjoy, beachchairs, snorkeling gear, fishing rod and even 2 kayaks. You can walk to many nearby restaurants, grocery stores and other shops. Public transportation is also steps away.

Top guest favorite
A private heated pool is featured at the edge of the terrace, offering views of the ocean and nearby islands. The clear blue water contrasts with the light-colored stone surrounding the pool, while lush greenery can be seen in the background against a clear sky.
Apartment in Little Bay
4.99 out of 5 average rating, 159 reviews

Stunning 2 BD Ocean View - Terraces Lt Bay

Treat yourself to the utmost stylish and modern ocean view apartment located in the exclusive Little Bay Hill . This spacious environment, is designed to be enjoyed as a family, has a terrace with stunning sea views, private pool, one master suites ( Japanese king bed and a walking closet), one bedroom suite with two twin size beds ( could be converted to king size bed ) . Welcome to Terraces Little Bay !

Superhost
A cozy sitting area is showcased, featuring a round coffee table surrounded by two comfortable chairs and a small dining table. A decorative mirror reflects light, while a lamp provides additional warmth. Artwork adorns the wall, contributing to the space's aesthetic.
Guest suite in Simpson Bay
4.82 out of 5 average rating, 215 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.

Top guest favorite
An inviting outdoor space features a private pool surrounded by lush greenery and sea views. Comfortable lounge chairs are positioned nearby, providing a serene spot to relax. Sunlight reflects off the water's surface, creating a tranquil atmosphere.
Apartment in Indigo bay
4.95 out of 5 average rating, 110 reviews

Independent apartment at the bottom of the villa – Indigo Bay

The Villa Stella apartment welcomes you in a unique setting with spectacular views of the Caribbean Sea. Located in a 24-hour secure residence, tranquility awaits. You will be just an 8-minute walk to Indigo Bay Beach and close to shops and restaurants in the Dutch side. Composed of 2 bedrooms and 2 bathrooms, you can relax in the pool/jacuzzi overlooking the bay.

Top guest favorite
An infinity pool extends toward the horizon, offering uninterrupted views of the Caribbean sea. The clear blue water reflects the sky, creating a serene atmosphere. Gentle slopes of greenery frame the scene, with a distant island visible on the water's surface.
Villa in Philipsburg
4.99 out of 5 average rating, 298 reviews

Villa Dream View Belair Sint Maarten SXM

Embrace the tranquility in a friendly tropical caribbean modern designed private villa with spacious rooms that are sure to keep you comfortable and feeling at home. Enjoy the sunny day with infinity pool overlooking caribbean sea or enjoy the sea view while watching the sailing huge cruise ships.

Guest favorite
A spacious outdoor lounge area is featured, with white sofas adorned with blue cushions. The view includes vibrant ocean hues and palm trees swaying gently. A dining table is positioned in the background, offering a scenic space for alfresco meals.
Apartment in Simpson Bay
4.95 out of 5 average rating, 107 reviews

Top of the art penthouse

Le Papillon enjoys one of the best locations on St. Martin, with many wonderful restaurants nearby and a beach that is close to private. If you would like to rent this property for less than what is required minimum please contact us and we will try to accommodate you.

Popular amenities for Simpson Bay vacation rentals

When is the best time to visit Simpson Bay?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Simpson Bay?

    Simpson Bay has more than 150 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Simpson Bay have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Villa Rentals in Simpson Bay?

    Enhance your stay in our Villa Rentals with the most popular amenities: over 30 homes with wifi, over 20 homes with a kitchen, over 30 homes with air conditioning, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there pet-friendly vacation rentals in Simpson Bay?

    Four-legged friends are welcome in Simpson Bay. Choose from more than 70 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Simpson Bay?

    Yes! Work meets play with ease at over 150 vacation rentals in Simpson Bay featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Simpson Bay vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 220 vacation homes with pools in Simpson Bay, available on Airbnb. Make a splash and soak up the sun in style!

  • Do serviced apartment rentals in Simpson Bay have a kitchen?

    Absolutely! We offer over 10 serviced apartment rentals with a kitchen in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in serviced apartment rentals in Simpson Bay?

    Experience the best of Simpson Bay with our serviced apartment rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do condo rentals in Simpson Bay have free parking?

    Absolutely! We offer over 60 condo rentals with free parking in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Simpson Bay have wifi?

    Absolutely! We offer over 150 apartment rentals with wifi in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Simpson Bay

  • Total vacation rentals

    Explore 360 vacation rentals in Simpson Bay

  • Nightly prices starting at

    Simpson Bay vacation rentals start at $30 per night before taxes and fees

  • Verified guest reviews

    Over 10,970 verified reviews to help you choose

  • Family-friendly vacation rentals

    150 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Vacation rentals with a pool

    220 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    350 of Simpson Bay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Simpson Bay rentals

  • 4.8 Average rating

    Simpson Bay stays are highly rated by guests—averaging 4.8 out of 5!

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