
Holiday rentals in Simpson Bay
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Top-rated holiday rentals in Simpson Bay
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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.

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

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.

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

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.

Turtle Den YOUR Maho Escape!
Welcome to Turtle Den, an enchanting ocean-inspired studio in the heart of Maho, St. Maarten. More than a stay, it's an immersive experience. Dive into a tranquil palette of oceanic hues, playful turtle motifs, and serene vibes. Just steps from Maho Beach, where planes land and take off, it's a front-row seat to breathtaking moments. Immerse in Maho's lively scene, surrounded by clubs and restaurants. Turtle Den is an invitation to savor the ocean's beauty and celebrate a world of whimsy.

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!

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

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

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.

Secret View amazing apartment- Private pool
Welcome to Secret View! An elegant and intimate retreat with a private pool and a spacious terrace set directly on the lagoon. Designed for couples seeking calm, romance and discretion, just minutes from vibrant Maho with its restaurants, bars and casinos, and Mullet Bay Beach, one of the island’s finest beaches with stunning turquoise waters. Free private parking. This hidden gem is the perfect setting for unforgettable moments together.

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.
Popular amenities for Simpson Bay holiday rentals
Other great holiday rentals in Simpson Bay

Modern / Cozy Studio in the center of Simpson Bay

Modern apartment with shared pool and generator

SeaWaves Beachfront 1 Brm Apt with Generator SXM

New: Superb Papaya Loft on the beach

Ocean Dream Villa

Emerald Apt at Maho Beach

Bright studio next to the beach

Beacon Hill Apartment Location Beaches, restaurants
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $273 SGD | $294 SGD | $267 SGD | $234 SGD | $213 SGD | $203 SGD | $217 SGD | $194 SGD | $178 SGD | $184 SGD | $203 SGD | $235 SGD |
| Avg. temp | 26°C | 26°C | 26°C | 27°C | 28°C | 29°C | 29°C | 29°C | 29°C | 29°C | 28°C | 27°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 360 holiday rentals in Simpson Bay

Nightly prices starting at
Simpson Bay holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 10,970 verified reviews to help you choose

Family-friendly holiday rentals
150 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 70 rentals that welcome pets

Holiday rentals with a pool
220 properties feature pools

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wifi availability
350 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!
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