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Vacation rentals in Simpson Bay

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Top-rated vacation rentals in Simpson Bay

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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
4.86 out of 5 average rating, 129 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.

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, 62 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 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, 228 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 modern two-story apartment structure features a covered balcony with seating for two. The exterior includes colorful accents and is surrounded by lush greenery. The parking area is enclosed by a wooden fence, accommodating multiple vehicles beneath the home.
Guesthouse in Simpson Bay
4.95 out of 5 average rating, 104 reviews

Simpson Bay Beach 1 bed Apt Topdeck. Ocean views

Modern 1 bedroom luxury apartment detached from the main house. Backup power Generator. Marble floors throughout. All stainless appliances in a full size kitchen. Free WIFI inside and on roof deck. Satellite TV. Additional Queen sofa sleeper in living room sleeps 2. Washer/Dryer. 90 steps to the beautiful Simpson Bay Beach. Private roof deck with 360° views. Grill, fridge and sink on deck. Beach chairs, beach towels umbrella, coolers. Parking right outside your gate. Onsite massage available

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, 210 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
Apartment in Simpson Bay
5 out of 5 average rating, 226 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
The image depicts a clear blue swimming pool surrounded by lounge chairs and tropical palm trees. In the background, the ocean can be seen alongside a beach area with a white railing, under a bright sky featuring fluffy clouds.
Apartment in Simpson Bay
5 out of 5 average rating, 8 reviews

Sunny Outlook - 1-bdr condo - Beachfront Residence

✨ Sunny Outlook with IRE Vacations ✨ This amazing 1 bedroom 1.5 bathroom unit is located at Palm Beach Condo’s, directly on Simpson Bay Beach. Palm beach is very convenient located in Simpson Bay, here you will find beach bars, restaurants and supermarkets within walking distance. Only a 10 minute drive from the airport. Palm beach offers you a large common pool and private access to the beach. Enjoy your day on the beach, at the pool or go on an adventure on our beautiful island!

Guest favorite
A light-filled living space features a comfortable beige sofa set, complemented by natural wood accents. Large windows provide a view of the ocean, while a doorway opens to an outdoor space adorned with greenery. Simple decor enhances the tranquil atmosphere of the room.
Condo in Simpson Bay
4.96 out of 5 average rating, 84 reviews

Hamaka condo, a beachfront retreat on Simpson Bay

Escape to the ultimate beachfront retreat at Hamaka, a fully equipped condo recently renovated to offer the perfect private beach escape with easy walking distance access to restaurants, bars, and nightly entertainment in Simpson Bay, Saint-Martin. Experience waking up to the sound of the waves and having your morning drink to the sight of the endless shades of the ocean. At the end of your day, unwind and enjoy the magnificent sunsets that this beautiful island has to offer.

Guest favorite
Apartment in Simpson Bay
4.93 out of 5 average rating, 139 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 bright living area is visible, featuring a comfortable couch and an armchair. The large glass doors showcase stunning ocean views and a spacious balcony, while soft drapes frame the opening, adding to the serene atmosphere.
Apartment in Simpson Bay
4.94 out of 5 average rating, 36 reviews

Premier Oceanfront Maho Beach

Escape to our premier corner suite at Maho Beach House, a true waterfront oasis in Sint Maarten. This chic retreat comfortably fits 2-4 guests and offers breathtaking, unobstructed sunset views over iconic Maho Beach. Watch planes from your private wrap-around balcony. Located in the heart of the action, you're steps from world-class dining and entertainment. Perfect for a memorable island getaway with a dedicated workspace and full kitchen.

Top guest favorite
A living room area features comfortable seating with colorful cushions against light blue walls. A dining table is set with breakfast items, including orange juice and pastries. Large windows allow natural light to illuminate the space, providing a view of the terrace and surrounding greenery.
Apartment in Simpson Bay
4.99 out of 5 average rating, 89 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 favorite
A bright open-concept living area features a modern dining table set for four, accompanied by stylish chairs. A comfortable seating space showcases a large sofa, with large glass doors revealing stunning views of lush greenery and distant mountains.
Apartment in Cupecoy Beach
4.96 out of 5 average rating, 28 reviews

B-304 Chic one bedroom with oceanview balcony

Welcome to our luxurious one-bedroom apartment, located on the third floor, offering panoramic golf and ocean views and a beautiful balcony. Prepare to immerse yourself in a world of opulence and tranquility, where every detail has been meticulously designed to create an extraordinary coastal retreat.<br><br>As you enter the apartment, you will be immediately captivated by the seamless blend of modern elegance and coastal charm.

Popular amenities for Simpson Bay vacation rentals

When is the best time to visit Simpson Bay?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$44,542 GYDG$47,888 GYDG$43,496 GYDG$38,059 GYDG$34,713 GYDG$33,040 GYDG$35,341 GYDG$31,577 GYDG$29,067 GYDG$29,904 GYDG$33,040 GYDG$38,268 GYD
Avg. temp26°C26°C26°C27°C28°C29°C29°C29°C29°C29°C28°C27°C

Frequently Asked Questions

  • What are the best places to stay in Simpson Bay?

    Simpson Bay has a variety of stays near the waterfront, marina, and lively marina-side neighborhoods. Accommodations range from family-friendly rentals to apartments near casual dining and nightlife, making it convenient for many types of travelers.

  • What are the best things to do in Simpson Bay with kids?

    Families can enjoy calm beaches, hands-on water sports, and kid-friendly boat tours around the bay. The area frequently suggests beachside snack shacks and casual spots suited for younger visitors.

  • What are some of the best things to do in Simpson Bay?

    Explore the bustling marina, join local boat excursions, or relax at sandy beaches lined with cafes. Simpson Bay is known for vibrant dining, water activities, and lively nightlife around the waterfront.

  • How is the weather in Simpson Bay?

    Simpson Bay has a warm, tropical climate, with year-round temperatures typically between 74–89°F (23–32°C) and the wettest period generally in autumn. Light clothing and sun protection are helpful for the sunny afternoons.

  • When is the best time to visit Simpson Bay?

    Late winter through spring is often recommended for milder weather and less rainfall, with bright days near 74–85°F (23–29°C). This period also sees fewer storms, making outdoor activities widely enjoyed.

  • What are the best places to visit in Simpson Bay?

    Simpson Bay has a lively marina area, scenic beaches, and a variety of beachside cafes and local shops. Many guests explore the waterfront for its blend of activity and relaxed Caribbean atmosphere.

  • What are some hiking trails in Simpson Bay?

    While Simpson Bay itself is more known for beaches and water activities, nature lovers often explore nearby hilly areas and coastal paths for gentle hikes. Consider casual walks along sandy stretches or around the lagoon for scenic views.

  • What are some family activities we can do in Simpson Bay?

    Families can spend time swimming, joining boat trips, or participating in beginner-friendly water sports. Picnic spots near the beach and casual local eateries help create a relaxed setting for all ages.

  • What are some of the best day trip ideas from Simpson Bay?

    Explore historic Philipsburg, take a boat tour to neighboring islands, or visit protected nature reserves around Sint Maarten. Markets, colonial-era forts, and guided eco-tours are frequently suggested for day adventures.

  • Are there any pet friendly accommodations available in Simpson Bay?

    There are pet-friendly vacation rentals in Simpson Bay, especially near residential and marina areas. Be sure to ask hosts about specific pet amenities or local outdoor spaces for companion animals.

  • What are some local tips for visiting Simpson Bay?

    It is helpful to have sun protection, as afternoons can be bright. Sampling both the French and Dutch culinary influences is often suggested, and carrying cash for small shops and open-air markets can make transactions smoother.

  • What is Simpson Bay known for?

    Simpson Bay is known for its relaxed beaches, vibrant marina scene, and mix of Caribbean and European–influenced dining. The area frequently draws visitors for water sports, seafood, and marina-side nightlife.

  • What are the best hidden gems to explore in Simpson Bay?

    Consider exploring quiet stretches of beach away from the main marina, small local bakeries, or roadside snack shacks featuring Caribbean specialties. Artists’ shops and lesser-known water taxi routes reveal another side of Simpson Bay.

  • What are the best foods to try in Simpson Bay?

    Simpson Bay has local dishes such as grilled fish, Johnny cakes, hearty stews, and seafood with French and Creole influences. Saltfish with Johnny cakes or fritters, and pastries from small bakeries, are frequently suggested for exploring regional flavors.

  • What should I bring for a trip to Simpson Bay?

    Lightweight, breathable clothing, swimwear, sturdy sandals, and plenty of sun protection are useful for exploring Simpson Bay. A reusable water bottle and rain jacket can also come in handy during brief showers.

  • What is the nightlife in Simpson Bay like?

    Simpson Bay has a lively nightlife, with casual bars, clubs, and waterfront venues featuring live music or DJs. The marina and beachside areas are known for after-dark dining and social gatherings.

  • What are the most popular events or festivals in Simpson Bay?

    Simpson Bay hosts lively regattas during late winter and early spring, with festive celebrations and boat parades. Cultural events, music nights, and culinary festivals also take place throughout the year, reflecting the island's blend of influences.

  • Are there family friendly vacation rentals in Simpson Bay?

    Simpson Bay has a range of family-friendly vacation rentals, with options near beaches, local shops, and casual restaurants. Many stays provide amenities such as kitchens and outdoor spaces suited for groups traveling with children.

Quick stats about vacation rentals in Simpson Bay

  • Total vacation rentals

    Explore 380 vacation rentals in Simpson Bay

  • Nightly prices starting at

    Simpson Bay vacation rentals start at G$8,365 GYD per night before taxes and fees

  • Verified guest reviews

    Over 11,390 verified reviews to help you choose

  • Family-friendly vacation rentals

    160 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Vacation rentals with a pool

    210 properties feature pools

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wi-Fi availability

    370 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!