
Vacation rentals in Simpson Bay
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Top-rated vacation 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.

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.

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.

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

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!

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.

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

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.

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.

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
Other great vacation rentals in Simpson Bay

Modern / Cozy Studio in the center of Simpson Bay

C344 - Lagoon view with balcony

Sea view terrace - Beachfront Studio

SBYC New large Studio Condo 872 sqft Heart of SXM

Renovated 2-Level Condo @ Simpson Bay Yacht Club

Beautiful White Sand, Sparkling Blue Waters, Sunny

TropiCasa - Watch sunsets surf the waves, 1BR

Simpsonbay Lagoonfront Studio with Stunning Views
When is the best time to visit Simpson Bay?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$44,542 GYD | G$47,888 GYD | G$43,496 GYD | G$38,059 GYD | G$34,713 GYD | G$33,040 GYD | G$35,341 GYD | G$31,577 GYD | G$29,067 GYD | G$29,904 GYD | G$33,040 GYD | G$38,268 GYD |
| 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 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!
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