Simpson Bay vacation rentals

We found 3,223 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Simpson Bay by choosing from 36 houses, 170 apartments, and other vacation rentals. Whether you're going on vacation with family or friends, vacation homes have the amenities you expect for your stay, which might include parking and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Simpson Bay

Showing deals for:Mar 6 - Mar 13

Image gallery for Luxury 5 Bedroom Villa

Pool Deck
10 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)

Luxury 5 Bedroom Villa

Les Terres Basses, Collectivité de Saint-Martin

10% off
Price is CA $1,886
CA $14,491 total
includes taxes & fees
Luxury 5 Bedroom Villa

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Simpson Bay

Why visit Simpson Bay

  • Stunning Beaches: Enjoy the beautiful sandy shores of Simpson Bay Beach, perfect for sunbathing and relaxation.
  • Outdoor Adventures: Experience a variety of family-friendly outdoor activities in the scenic parks and vibrant atmosphere.
  • Charming Accommodations: Choose from a selection of vacation rentals, including luxurious villas and cozy apartments.
  • Romantic Getaways: Ideal for couples, Simpson Bay offers romantic seaside retreats with breathtaking views.
  • Local Attractions: Explore nearby neighborhoods and enjoy the lively culture and attractions that Sint Maarten has to offer.

Popular types of accommodation in Simpson Bay

Planning a getaway to Simpson Bay? You're in for a treat. This vibrant destination offers a variety of vacation rentals, from stunning condos and luxurious villas to cozy apartments. Whether you're seeking Simpson Bay beach rentals or a charming vacation cottage, you'll find the perfect spot to relax in Sint Maarten. Explore our selection of St. Maarten vacation rentals and discover the ideal home base for your adventures.

  • Condos: The most sought-after vacation rental option in Simpson Bay, ideal for those who prefer the comforts of home with resort-style amenities.
  • Villas: A luxurious choice for travelers looking for spacious accommodations and stunning views, perfect for families or groups.
  • Apartments: A versatile lodging option, offering convenient access to local attractions and a cozy atmosphere.
  • Houses: Great for larger gatherings, these homes provide privacy and a home-like experience.
  • Guest Houses: A charming and often budget-friendly choice, providing a more personal touch to your stay.**

Top attractions in and around Simpson Bay

Simpson Bay, Sint Maarten, is a perfect destination for beach lovers and outdoor enthusiasts. With its stunning beaches and parks, you can enjoy a family-friendly experience by exploring the local attractions. Don't miss out on the beautiful Simpson Bay Beach and consider vacation rentals for an extended stay to fully immerse yourself in the scenery and activities this vibrant area has to offer.

  • Simpson Bay Beach: A picturesque stretch of golden sand, perfect for sunbathing and swimming. The beach vibes here are relaxed, making it an ideal spot to unwind and enjoy the stunning Caribbean views.
  • Seaside Nature Park: Located 1.6km from Simpson Bay, this eco-friendly park is great for families seeking outdoor adventure. Explore lush trails, spot local wildlife, and enjoy activities like hiking and birdwatching.
  • Kim Sha Beach: Another beautiful beach in Simpson Bay, Kim Sha offers vibrant beach vibes, excellent swimming conditions, and nearby dining options, making it a lively spot for both relaxation and fun.

Things to do recommended for couples

For a romantic getaway in Simpson Bay, take a scenic stroll along the Philipsburg Boardwalk, just 4.8km away. Enjoy the beachy atmosphere and captivating views, perfect for couples looking to connect and create lasting memories together.

Things to do recommended for families

While in Simpson Bay, families can experience the thrill of Rainforest Adventures St. Maarten, a recreation park located 3.2km away. With its wellness vibes and fun activities, it's an ideal spot for relaxation and enjoyment for both kids and adults.

Things to do recommended for groups

Enjoy a round of golf at Mullet Bay Golf, just 3.2km from Simpson Bay, or explore the vibrant shops at Front Street District and Harbour Point Village, both 6.4km away, perfect for family bonding and local experiences.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Simpson Bay

If you're planning a trip with a group, family, pets, or looking for extended stays, it's important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Simpson Bay with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Simpson Bay with young kids: Traveling with young children can present its own set of challenges. It's essential to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Simpson Bay: For many families, a trip just wouldn’t feel right without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone, including your pet, feels comfortably at home.
  • Planning for a long term stay visiting Simpson Bay: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Simpson Bay

Simpson Bay, Sint Maarten, offers a delightful blend of romantic seaside getaways and family-friendly adventures. With stunning beach views and some of the best beaches in the Caribbean, you’ll find charming tropical retreats and fantastic stays just moments away. Whether you're soaking up the sun on the sandy shores or exploring the vibrant atmosphere of nearby neighborhoods, Simpson Bay is the perfect destination for unforgettable outdoor escapades and scenic experiences.

  • Cole Bay: Located a mere 1.4km from Simpson Bay, Cole Bay is a vibrant city that offers a delightful blend of beach and outdoor experiences. Visitors can enjoy stunning scenery while exploring the local resorts and boardwalk. The area is renowned for its beautiful beaches, including a nudist beach that caters to those seeking a more liberated experience. With its close proximity to the bay, Cole Bay is perfect for water activities and relaxation, making it a must-visit for those wanting to soak up the sun.
  • Beacon Hill: Nestled within the Simpson Bay area, Beacon Hill is a charming village that attracts tourists with its beautiful beaches and outdoor activities. The area is known for its picturesque scenery, making it an ideal getaway for nature lovers. Beacon Hill features a variety of resorts and educational venues, along with a lovely boardwalk perfect for leisurely strolls. The nearby beaches and nudist beach provide ample opportunities for sunbathing and swimming, ensuring visitors have a memorable experience.
  • Pelican Key: Situated around Simpson Bay, Pelican Key is a serene neighborhood that offers travelers a peaceful retreat. Known for its stunning beaches and outdoor scenery, Pelican Key is an excellent destination for those seeking relaxation and adventure. The area is home to various resorts and educational activities, along with a scenic boardwalk that invites exploration. With its proximity to beautiful beaches and a nudist beach, Pelican Key is perfect for vacationers looking to unwind in a tropical paradise.

Best time to go to Simpson Bay

If you're planning a trip to Simpson Bay, it's a good idea to check both the weather and property rates. The warmest month is September. Peak season runs from January to March, while off-peak times, like August to October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January78.3°F (25.7°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
February77.7°F (25.4°C)No Rain (Dry)Mostly SunnyModerately HighAverage
March77.5°F (25.3°C)No Rain (Dry)Mostly SunnyModerately HighSlightly High
April78.4°F (25.8°C)No Rain (Dry)Mostly SunnyAverageAverage
May80.1°F (26.7°C)Light RainMostly SunnyAverageAverage
June81.5°F (27.5°C)Light RainMostly SunnyAverageAverage
July82.0°F (27.8°C)Light RainMostly SunnyAverageAverage
August82.6°F (28.1°C)Light RainMostly SunnyModerately LowAverage
September82.9°F (28.3°C)Light RainMostly SunnyModerately LowSlightly Low
October82.6°F (28.1°C)Light RainMostly CloudyModerately LowSlightly Low
November81.3°F (27.4°C)Light RainMostly CloudyAverageSlightly Low
December79.7°F (26.5°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Vrbo Trips: Effortless planning

Vrbo's Trip Board is a fantastic tool that allows you to easily plan your journeys, pick up right where you left off, and manage your travel arrangements. You can conveniently access the properties you've saved or booked, which are now categorized under Potential, Upcoming, or Current Trips. To start using the Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Head to the lively city of Simpson Bay

Enjoy the live music and other features of Simpson Bay. This romantic city is known for its beaches, restaurants and casino gaming. Maho Beach and Orient Bay Beach are just a couple of the must-sees in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Simpson Bay

Are you hoping to discover top things to see and do in the city? Venture out of your vacation home and check out everything that makes Simpson Bay a fun spot to vacation. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Mullet Bay Golf (1.6 mi / 2.6 km)
  • Aurora International Golf Club (9.9 mi / 16 km)

Exploring the beaches and other natural features in Simpson Bay

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Simpson Bay is a great spot to appreciate mother nature. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Maho Beach (1.6 mi / 2.5 km)
  • Orient Bay Beach (6.1 mi / 9.9 km)
  • Kim Sha Beach (0.3 mi / 0.5 km)
  • Flamingo Beach (0.5 mi / 0.8 km)
  • Simpson Bay Beach (1 mi / 1.6 km)
  • Maho Bay (1.6 mi / 2.5 km)

Seasonal weather averages in Simpson Bay

If you're hoping to enjoy some warm-weather activities on your vacation, September, August, October and July are the hottest months to visit, when temperatures average 83°F.

Transportation to and around Simpson Bay

The nearest airport is in Princess Juliana Intl. Airport (SXM), located 1.1 mi (1.8 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Grand Case (SFG-L'Esperance), which is 5.5 mi (8.8 km) away.

Frequently asked questions

What is the best area to stay in Simpson Bay when booking a vacation rental?
When considering a vacation rental in Simpson Bay, Sint Maarten, the best area to stay is the Simpson Bay Village. This vibrant neighbourhood offers a delightful mix of local charm and modern conveniences, making it an ideal base for vacationmakers. The area is known for its picturesque marina, where you can enjoy stunning views of the yachts and sailboats.

One of the top attractions nearby is Maho Beach, famous for its close proximity to the airport and the exhilarating experience of watching planes land just overhead. Additionally, the lively nightlife and dining options along the waterfront add to the area's allure, with a variety of restaurants serving delicious local and international cuisine.
How much does it cost to rent a vacation home in Simpson Bay?
Prices for vacation rentals in Simpson Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Simpson Bay to more spacious homes.
Are there any discounts for Simpson Bay vacation house rentals?
You can find great discounts on house rentals in Simpson Bay on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Simpson Bay?
For renting a beach house in Simpson Bay, Sint Maarten, the vibrant waterfront area along Simpson Bay Beach is an excellent choice. This stretch of sandy shore is known for its stunning sunsets and lively atmosphere, with a variety of vacation rentals available, ranging from modern villas to charming beach cottages. Many properties in this area come with amenities such as private pools, spacious terraces, and direct beach access, creating a superb setting for relaxation and entertainment.

In addition to the beach, travellers can enjoy proximity to local dining and nightlife options, as the area boasts a selection of restaurants and bars that cater to diverse tastes. The nearby Simpson Bay Lagoon offers opportunities for water sports, including sailing and kayaking, making it ideal for those seeking adventure. Find your rental near the beach in Simpson Bay.
What is the most popular type of vacation rental accomodation in Simpson Bay?
In Simpson Bay, apartments are the most popular type of vacation rental, with approximately 129 available throughout the area. Many of these apartments are located close to the stunning beaches and vibrant nightlife, offering guests easy access to local attractions such as the Simpson Bay Lagoon and Maho Beach. Most apartments come equipped with amenities like fully fitted kitchens, comfortable living areas, and often balconies or terraces that provide beautiful views of the surrounding landscape.
Are there any family house rentals in Simpson Bay?
In Simpson Bay, Sint Maarten, there are numerous family-friendly house rentals available—around 165 in total. This vibrant area is renowned for its stunning beaches and lively atmosphere, making it an excellent choice for families. Many of these properties boast spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can enjoy playtime. Visitors can also find amenities such as private pools, air conditioning, and laundry facilities, ensuring a comfortable stay.
Can I rent a vacation home with a pool or hot tub in Simpson Bay?
In Simpson Bay, Sint Maarten, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 268 options to choose from. This lively area is known for its beautiful beaches and vibrant nightlife, making it a popular destination for travellers. Find your rental in Simpson Bay with a pool or a hot tub.
Can I find long-stay vacation rentals in Simpson Bay?
A long-stay vacation rental in Simpson Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Simpson Bay?
In Simpson Bay, there are numerous pet-friendly house rentals available, with around 61 options to choose from. This vibrant area is known for its stunning beaches and lively atmosphere, making it an excellent choice for travellers with pets. Many of the vacation rentals feature amenities such as private pools, outdoor terraces, and fully equipped kitchens, providing a comfortable home away from home.
Are there any remote work vacation rentals in Simpson Bay?
In Simpson Bay, Sint Maarten, there is a substantial selection of remote work vacation rentals, with around 301 options available. This vibrant area is known for its stunning beaches and lively atmosphere, making it an ideal spot for both work and leisure. Many properties cater specifically to remote workers, featuring dedicated workspaces equipped with desks, comfortable chairs, and computer monitors. High-speed Wi-Fi is commonly available, ensuring seamless connectivity for those working from home or remotely. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Simpson Bay vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Simpson Bay with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Simpson Bay?
In Simpson Bay, popular rental amenities include pools, kitchens equipped with essential items such as refrigerators, cookware, dishware, and utensils, as well as coffee makers for a convenient start to the day. Many properties provide a refreshing pool area, superb for relaxation after enjoying the nearby beaches and vibrant nightlife.
When is the best time to visit Simpson Bay for a vacation rental?
September is the most popular month to visit Simpson Bay, as it marks the tail end of the peak season from July to September, when travellers flock to this beautiful island for sun-soaked vacations. During this time, the weather is typically warm, with average temperatures in the low 30s Celsius, making it superb for beach days, water sports, and exploring the vibrant local culture.

As the summer crowds begin to thin, September offers a more relaxed atmosphere while still providing plenty of opportunities for outdoor activities. You can indulge in everything from sailing and snorkelling to enjoying the lively beach bars and restaurants that line the coast. The stunning beaches, such as Maho and Simpson Bay Beach, are ideal for sunbathing and swimming, ensuring you can soak up the Caribbean sun in comfort.

For those seeking good value, October is a great choice, as prices for vacation rentals often drop significantly after the busy summer season. This quieter month allows travellers to enjoy the island's natural beauty and attractions without the hustle and bustle, making it a superb time for peaceful exploration. You can take leisurely walks along the beautiful coastline or venture into the local markets for a taste of authentic Caribbean life.
How early should I book a Simpson Bay vacation rental?
Book your Simpson Bay vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Simpson Bay?
In Simpson Bay, Sint Maarten, visitors can enjoy a variety of attractions that highlight the area's vibrant culture and stunning natural beauty. The Simpson Bay Beach is a prime destination, offering soft sands and clear waters, superb for sunbathing and water sports. Nearby, the Simpson Bay Lagoon is a popular spot for yacht watching and enjoying the scenic waterfront.

For those interested in nightlife, the area is home to numerous bars and restaurants along the waterfront, providing a lively atmosphere after sunset. The nearby Pelican Key offers a more tranquil experience with beautiful beaches and luxury resorts, making it ideal for relaxation.
Can I change or cancel my Simpson Bay home rental booking on Vrbo?
To find Simpson Bay vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Simpson Bay vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More Vacation Ideas