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 condo rentals in Simpson Bay have self check-in?

Absolutely! We offer over 20 condo rentals with self check-in in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

Do house rentals in Simpson Bay have a bbq area?

Absolutely! We offer over 20 house rentals with a bbq area 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 10 homes with a bbq area, 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 house rentals on Airbnb with pools?

Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Simpson Bay, available on Airbnb. Make a splash and soak up the sun in style!

How much does it cost to stay in villa rentals in Simpson Bay?

Experience the best of Simpson Bay with our villa rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Do serviced apartment rentals in Simpson Bay have wifi?

Absolutely! We offer over 20 serviced apartment rentals with wifi in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

Do apartment rentals in Simpson Bay have a gym?

Absolutely! We offer over 50 apartment rentals with a gym in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

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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Guest favorite

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

4.89 out of 5 average rating, 114 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 cozy living area features a comfortable gray sofa and a wooden coffee table. Two windows offer expansive views of the ocean, with light reflecting off the water. Beams stretch across the ceiling, enhancing the airy feel of the space.

Condo in Simpson Bay

4.8 out of 5 average rating, 171 reviews

Oceanfront w Pool | Maho Beach area

Location , Location Location ! You can not get any closer to the ocean than in this cliff side apartment. The sound of waves crashing below and incredible ocean views from every room. The sunrise is magical everyday and by night the glowing lights of Simpson bay. This cliff side apartment has everything you need for a dream stay away from the crowds. . Just steps from 4 beaches Simpson bay, Mullet bay, burgeux bay and a 5minute walk to the world famous Maho Beach with its famous plane landings

Guest favorite

A white, modern condo complex is set atop a rocky outcrop overlooking a sandy beach. Waves gently lapping at the shore and a clear blue sky serve as a backdrop, creating a serene coastal atmosphere.

Condo in Simpson Bay

4.98 out of 5 average rating, 53 reviews

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!

Top guest favorite

A bright living area features large glass doors that open to a private outdoor space. A comfortable sofa and a coffee table are positioned on a light-toned rug. A TV is mounted on a sleek white cabinet, while wooden accents add warmth to the design.

Apartment in Simpson Bay

5 out of 5 average rating, 49 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.

Guest favorite

A dining area features a modern table with four chairs, positioned near large windows showcasing panoramic views of the turquoise sea and sandy beach. A wall mirror reflects the inviting atmosphere, while lush greenery can be seen outside, enhancing the coastal ambiance.

Apartment

4.96 out of 5 average rating, 201 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.

Guest favorite

A well-lit bedroom features a spacious bed with crisp white linens and various decorative pillows. Matching bedside tables hold stylish lamps. A wall-mounted television is positioned in front of the bed, while light streaming through partially opened shutters adds a bright touch to the room.

Home in Simpson Bay

5 out of 5 average rating, 10 reviews

The beachcomber

Welcome to your perfect island retreat! Located in the heart of Beacon Hill, this cozy unit offers the ideal home base for exploring all that Sint Maarten has to offer. Just steps away from the island’s top attractions, you'll be within walking distance to: Maho Beach, Casinos,Restaurants & Bars. This unit is perfect for couples or solo travelers. Don’t miss out on the best location on the island – book your stay in Beacon Hill today and live like a local just steps from the action!

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, 213 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

Superhost

A spacious swimming pool features clear blue water and is surrounded by palm trees. Lush landscaping adds to the serene environment. The backdrop showcases the resort building and outdoor dining area, all bathed in natural light under a partly cloudy sky.

Apartment in Cole Bay

4.94 out of 5 average rating, 18 reviews

Beachfront Royal Palm 1-BR

This one-bedroom unit is located on the 4th floor of the Royal Palm Hilton Vacation Club in Simpson Bay, St Maarten. This property boasts direct beach access and stunning ocean views! Inside you’ll find a spacious open-plan living area with a pull out sofa, and the modern kitchen is fully equipped. Situated in the heart of it all, close to restaurants, bars & nightlife! Please note: The Royal Palm requires a $250 refundable security deposit at check-in.

Top guest favorite

An outdoor terrace features comfortable white lounge furniture arranged around a coffee table. Sun loungers are positioned beside a private infinity pool, overlooking the ocean and distant boats. The scene is framed by tropical plants and a clear blue sky, enhancing the serene coastal environment.

Loft

4.99 out of 5 average rating, 161 reviews

Sea Loft, Breathtaking View – Private Pool

* 200 m² loft * Exceptional sea view * Private pool * 250 meters from the small beach of Galisbay * Terrace with deckchairs, garden furniture, outdoor table and BBQ * Office space * 100 Mbps WiFi * 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, shops and other stores * 5 min to the pier for Saint-Barth and Anguilla, and the taxi station

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, 153 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 !

Guest favorite

A spacious balcony offers views of a marina filled with yachts and sailboats. A comfortable chair is positioned to enjoy the scenery, with distant green hills and a blue sky enhancing the tranquil waterscape.

Condo in Simpson Bay

4.97 out of 5 average rating, 58 reviews

SkyPort Condo

- Keyless Entry - Wifi - Air Conditioning - Elevator - Lagoon View - Yachts and Marina View - Street/Village View - 65 Inch Smart TV - Internet TV Services - Soundbar with Subwoofer - Full Kitchen - Laundry/Social Bathroom - Great Location in Simpson Bay to Explore the Area - Walking distance to Restaurants, Bars, Grocery Stores, Pharmacy, ATMs, Casino, Gas Station, Car Rentals, Beach

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, 103 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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Popular amenities for Simpson Bay vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Simpson Bay

Superhost

A balcony offers a stunning lagoon view, framed by sliding glass doors. Two armchairs are positioned around a small table, providing a cozy seating area. The landscape features rolling hills and a sparkling waterway, visible in clear daylight.

Condo in Cole Bay

4.83 out of 5 average rating, 12 reviews

B256 - Amazing Top Floor Apartment With Balcony

Top guest favorite

A spacious outdoor terrace features a stunning infinity pool overlooking the sea, complemented by comfortable sun loungers. A shaded dining area with a stylish table set for gatherings is visible, showcasing panoramic views of the coastline and vibrant blue ocean.

Home in Upper Prince's Quarter

5 out of 5 average rating, 15 reviews

Breathtaking view of St Barth – 8 people

Guest favorite

A spacious living area features large floor-to-ceiling windows, offering captivating views of the turquoise Caribbean sea and blue skies. A modern coffee table is set with a bowl of fruit and two glasses, complemented by soft drapes that frame the scenic backdrop.

Apartment in Cupecoy Beach

4.89 out of 5 average rating, 75 reviews

A-1001 1 bedroom with incredible view

Top guest favorite

A bright living area features large windows that allow natural light to fill the space, offering views of the outdoors. A comfortable gray sofa is positioned near a round dining table with four chairs. Decorative elements, including a small centerpiece and a television, complete the inviting setting.

Apartment in Lowlands

5 out of 5 average rating, 19 reviews

Stunning Gem in Prime Location

Guest favorite

A stunning view of the turquoise ocean is showcased under a bright blue sky with fluffy clouds. Palm trees frame a peaceful swimming pool located within the complex, enhancing the tropical atmosphere.

Apartment in Simpson Bay

5 out of 5 average rating, 6 reviews

*New* SeaBliss 3BR Palm Beach Condo. Simpson Bay

Guest favorite

A spacious bedroom is showcased with a large bed featuring neutral-toned linens. A panoramic window offers stunning views of the ocean and coastline, framed by soft drapes. A bedside table holds a lamp, and a television is positioned across the room, enhancing the modern decor.

Home in Upper Prince's Quarter

5 out of 5 average rating, 62 reviews

Endless Views @ Acqua Bleu

Top guest favorite

A spacious living area is shown with large open doors leading to a private terrace. Light-colored furniture is arranged comfortably, with a dining table ready for meals. The ocean view is visible in the background, providing a serene backdrop to the inviting space.

Apartment in Grand Case

5 out of 5 average rating, 6 reviews

1 bd Grand-Case beach

Top guest favorite

A panoramic view of turquoise waters showcases numerous boats anchored in the distance, framed by lush palm trees. A rainbow appears across the sky, adding a colorful touch to the serene coastal landscape.

Townhouse in Cole Bay

5 out of 5 average rating, 99 reviews

Hillside Beach Townhouse Simpson Bay

Show all

Quick stats about vacation rentals in Simpson Bay

Total rentals
360 properties
Nightly prices starting at
€ 26 before taxes and fees
Total number of reviews
11K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
240 properties have a pool

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 condo rentals in Simpson Bay have self check-in?
Absolutely! We offer over 20 condo rentals with self check-in in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Simpson Bay have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area 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 10 homes with a bbq area, 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 house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Simpson Bay, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in villa rentals in Simpson Bay?
Experience the best of Simpson Bay with our villa rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do serviced apartment rentals in Simpson Bay have wifi?
Absolutely! We offer over 20 serviced apartment rentals with wifi in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Simpson Bay have a gym?
Absolutely! We offer over 50 apartment rentals with a gym in Simpson Bay. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Simpson Bay

Top-rated vacation rentals in Simpson Bay

Vacation rentals for every style

Popular amenities for Simpson Bay vacation rentals

Other great vacation rentals in Simpson Bay

Quick stats about vacation rentals in Simpson Bay

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with a pool

Frequently Asked Questions

Destinations to explore