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Holiday rentals in Simpson Bay

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Top-rated holiday rentals in Simpson Bay

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Guest favourite
Flat in Simpson Bay
5 out of 5 average rating, 12 reviews

A beautiful apartment facing the Caribbean sea

This apartment is a dream. It has been renovated with luxurious materials and furnitures and it faces the sea. The beach is downstairs, 1 minute away. Every morning you wake up with the sunrise and every evening you enjoy the sunset. It has a private terrasse outside which gives you privacy (with 2 beach chairs on it). It is located in Beacon Hill, close to Maho and Simpson Bay. You can enjoy the serenity at your apartment and also enjoy the bars, clubs and restaurant within a walking distance.

Top guest favourite
The private patio features a saltwater pool with ocean views, complemented by lounge chairs and tropical plants. Soft clouds drift overhead, enhancing the serene atmosphere. Nearby, a dining area offers an inviting space for meals while overlooking the lush garden and the expansive sea.
Home in Cole Bay
4.86 out of 5 average rating, 28 reviews

Luxury Villa Turquoise Heaven in Pelican Key

Welcome to Villa Turquoise Heaven- Modern Luxury in Pelican Key, SXM Experience the pinnacle of Caribbean elegance at Villa Turquoise Heaven, the newest luxury villa in the exclusive Tepui Residence. Designed for relaxation and style, this modern retreat offers a seamless blend of indoor-outdoor living with unparalleled views of the turquoise Caribbean Sea. From waking up to the gentle sound of waves to savoring sunsets from your private infinity pool, Villa TH offers an unforgettable escape.

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.
Flat in Simpson Bay
4.88 out of 5 average rating, 238 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.
Guest house in Simpson Bay
4.95 out of 5 average rating, 106 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

Guest favourite
A spacious bedroom features a large bed adorned with white linens and a soft gray throw. Three framed black-and-white prints are displayed on the wall above the bed, while a window offers views of the beach and ocean beyond.
Apartment in Lowlands
4.92 out of 5 average rating, 139 reviews

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

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.
Flat in Simpson Bay
4.95 out of 5 average rating, 226 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 favourite
Flat in Simpson Bay
5 out of 5 average rating, 236 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
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.
Flat in Simpson Bay
4.95 out of 5 average rating, 37 reviews

The Pineapple Suite

Discover The Pineapple Suite, a chic 2-bedroom retreat accommodating up to 4 guests, nestled within the secure confines of Simpson Bay Yacht Club's gated community. Unwind in modern luxury, relish on-site amenities like the two swimming pools, tennis courts, bbq area and soak in breathtaking views of the yachts, lagoon, hills and sunset from your balcony. Conveniently located near the airport in Simpson Bay within walking distance from restaurants, the beach, bars and supermarkets.

Guest favourite
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.
Apartment in Simpson Bay
4.96 out of 5 average rating, 93 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 favourite
Flat in Simpson Bay
4.93 out of 5 average rating, 143 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

Guest favourite
A stunning sunset is captured over the calm sea, reflecting vibrant colors onto the water's surface. In the foreground, a serene pool mirrors the sky, enhancing the tranquil ambiance of the outdoor space. The silhouette of trees adds a natural element to the scene.
Villa in Simpson Bay
4.96 out of 5 average rating, 83 reviews

Waterfront "Bonjour" Beacon Hill St Maarten

This stunning 4-bedrooms, 4 bathrooms villa overlooks Maho Bay and provides a front row seat to beautiful SXM sunsets, and over the famous Maho Beach. Enjoy the views while taking a dip in the home’s infinity pool overlooking the ocean or from its multiple outdoor dining and seating options conveniently and securely located minutes from restaurants, bars, nightlife, Maho Market and more, steps away from direct beach access to Simpson Bay Beach. Back up Diesel Generator

Top guest favourite
Flat in Cole Bay
5 out of 5 average rating, 11 reviews

Beautiful, bright apartment with a lagoon view in Simpson Bay

Profitez d’un séjour inoubliable dans cet appartement confortable avec vue sur le lagon. Le logement dispose d’un espace de vie agréable, soigneusement aménagé pour votre confort. Le balcon vous permettra de savourer vos repas ou un café face au lagon, avec une vue apaisante à toute heure de la journée. La cuisine est entièrement équipée. Situé dans une résidence calme, vous êtes à proximité des plages, restaurants, commerces et activités incontournables de l’île.

Popular amenities for Simpson Bay holiday rentals

When is the best time to visit Simpson Bay?

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Avg. price$271 SGD$292 SGD$265 SGD$232 SGD$211 SGD$201 SGD$215 SGD$192 SGD$177 SGD$191 SGD$215 SGD$302 SGD
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 holiday rentals in Simpson Bay

  • Total holiday rentals

    Explore 390 holiday rentals in Simpson Bay

  • Nightly prices starting at

    Simpson Bay holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 12,660 verified reviews to help you choose

  • Family-friendly holiday rentals

    180 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 80 rentals that welcome pets

  • Holiday rentals with a pool

    230 properties feature pools

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wifi availability

    380 of Simpson Bay holiday 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!