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Vacation rentals in Simpson Bay

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Top-rated vacation rentals in Simpson Bay

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

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Guest favourite
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, 137 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 favourite
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, 65 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 favourite
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, 230 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 favourite
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, 105 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 favourite
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, 217 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 favourite
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
4.97 out of 5 average rating, 38 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 favourite
Apartment in Simpson Bay
5 out of 5 average rating, 228 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 favourite
Apartment in Simpson Bay
4.93 out of 5 average rating, 140 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 favourite
Condo in Maho
4.91 out of 5 average rating, 234 reviews

Maho Love Shack: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 for you to indulge.

Top guest favourite
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
4.96 out of 5 average rating, 27 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 favourite
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 in Marigot
4.99 out of 5 average rating, 179 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 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 favourite
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
4.9 out of 5 average rating, 39 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.

Popular amenities for Simpson Bay vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Simpson Bay

Guest favourite
Apartment in Simpson Bay
5 out of 5 average rating, 9 reviews

Seafront Studio C3

Guest favourite
An outdoor seating area offers a spacious table and comfortable couch, framed by a wooden pergola. Views of the ocean and sailboats are visible in the distance, while tropical plants add a natural touch to the relaxed atmosphere.
Townhouse in Billy Folly Hill
4.94 out of 5 average rating, 90 reviews

Pelican Sea View 1bdrm Maison Mazu

Apartment in Simpson Bay
5 out of 5 average rating, 4 reviews

Lux 2BR/2.5BA Unit, Simpson Bay

Apartment in Cole Bay
4.86 out of 5 average rating, 7 reviews

C351 – Elegance with Stunning Lagon Views

Guest favourite
Apartment in Maho Beach
5 out of 5 average rating, 7 reviews

Escapes at The Emerald

Guest favourite
Apartment in Lowlands
5 out of 5 average rating, 15 reviews

Jordan village, 5 min walk to the beach

Guest favourite
Apartment in Simpson Bay
4.88 out of 5 average rating, 8 reviews

Simpsonbay Lagoonfront Studio with Stunning Views

Top guest favourite
An aerial view captures the vibrant landscape of Simpson Bay Yacht Club, revealing the layout of the community, including palm trees, two swimming pools, and tennis courts. The calm turquoise waters border the marina, and the lush green hills rise in the background, complementing the scene.
Apartment in Simpson Bay
4.97 out of 5 average rating, 34 reviews

The Pineapple Suite

When is the best time to visit Simpson Bay?

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Avg. price$291 CAD$313 CAD$284 CAD$249 CAD$227 CAD$216 CAD$231 CAD$206 CAD$190 CAD$205 CAD$231 CAD$324 CAD
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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 $55 CAD 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 and 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

  • Wifi availability

    370 of Simpson Bay vacation rentals include wifi 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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