Simpson Bay vacation rentals

We found 3,175 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Simpson Bay by choosing from 81 houses, 136 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:Oct 31 - Nov 7

Image gallery for Luxury 5 Bedroom Villa

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

Luxury 5 Bedroom Villa

Les Terres Basses, Collectivité de Saint-Martin

9% off
Price is $1,314
$9,198 for 7 nights
All fees included
Luxury 5 Bedroom Villa

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Find out more about Simpson Bay

Find out more about Simpson Bay

Why visit Simpson Bay

  1. Stunning Beaches: Enjoy the beautiful Simpson Bay Beach, perfect for sunbathing and water sports.
  2. Outdoor Adventures: Explore nearby parks and enjoy family-friendly outdoor activities amidst breathtaking scenery.
  3. Charming Coastal Vibe: Experience the relaxed atmosphere and picturesque views that make Simpson Bay unique.
  4. Vibrant Local Culture: Discover nearby neighborhoods with panoramic vistas and rich local culture.
  5. Diverse Accommodations: Choose from a variety of vacation rentals, including condos, villas, and apartments with stunning views.

Popular types of accommodation in Simpson Bay

If you’re planning a getaway in Simpson Bay, you’ll find a variety of fantastic vacation rentals to suit your needs. The most popular options include condos, villas, and apartments, each offering unique amenities and stunning views. Whether you’re seeking a cozy retreat or a luxurious stay, our Simpson Bay vacation rentals provide the perfect base for your adventures. Explore the beauty of this vibrant destination with comfort and ease!

  • Condos: The top choice for vacation rentals in Simpson Bay, offering modern amenities and stunning views.
  • Villas: A luxurious option for travelers seeking spacious accommodations and private outdoor areas.
  • Apartments: A convenient and comfortable option, perfect for visitors wanting a home-like atmosphere.
  • Houses: Ideal for families or groups, providing a personalized and intimate stay.
  • Cottages: Charming and cozy, perfect for a quaint getaway close to nature.**

Top attractions in and around Simpson Bay

Simpson Bay offers a perfect getaway for beach lovers and outdoor enthusiasts, featuring stunning scenery and a relaxed atmosphere. Key attractions include the beautiful Simpson Bay Beach and nearby parks, making it ideal for families looking to enjoy outdoor experiences. With its charming coastal vibe, Simpson Bay is a fantastic destination for those seeking sun, sand, and adventure in Sint Maarten.

  1. Maho Beach: Known for its stunning turquoise waters and soft white sand, Maho Beach offers a unique experience as planes fly low overhead during landing at the nearby airport, creating a thrilling spectacle for visitors.
  2. Seaside Nature Park: This eco-friendly park features outdoor activities suitable for families, including hiking trails and wildlife observation, all set in a lush natural environment that promotes conservation and appreciation of local flora and fauna.
  3. Simpson Bay Beach: Located right within Simpson Bay, this beach is perfect for sunbathing and swimming, with a vibrant atmosphere and plenty of nearby amenities, making it a favorite for both locals and tourists.

Things to do recommended for couples

For a romantic getaway in Simpson Bay, don't miss a stroll along the Philipsburg Boardwalk, just 3 miles away. Enjoy the beach vibes and captivating views as you create unforgettable memories together in this beautiful setting.

Things to do recommended for families

Your family will have a blast at Rainforest Adventures St. Maarten, located 2 miles from Simpson Bay. This recreation park offers a perfect blend of fun and relaxation, making it an ideal spot for kids to explore and enjoy the beauty of nature.

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

If you’re traveling with a group, family, or pets, or if you’re considering extended stays, it’s important to prioritize your preferences when searching. Here are some helpful Vrbo booking tips for you.

  • Traveling to Simpson Bay with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Simpson Bay with young kids: Traveling with young kids can be tough. It’s important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, you might want to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Simpson Bay: For many, a family vacation isn't truly complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Simpson Bay: If you’re seeking vacation rentals with special offers 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 parking, a well-equipped kitchen, or a private pool in your search for the perfect getaway.

Where to stay in and around Simpson Bay

Simpson Bay, Sint Maarten, is a stunning destination perfect for beach lovers and outdoor enthusiasts. With its breathtaking sea views and easy beach access, visitors can enjoy a romantic atmosphere or family-friendly excursions. Explore nearby neighborhoods offering panoramic vistas and vibrant local culture, making it an ideal vacation spot for relaxation and adventure. Whether you're seeking scenic beauty or memorable experiences, Simpson Bay has something for everyone.

  • Beacon Hill: Nestled within the scenic area of Simpson Bay, Beacon Hill is a charming village that captures the essence of Caribbean beauty. Known for its stunning beaches and outdoor recreational opportunities, travelers flock here for the breathtaking scenery and relaxation. The village features a welcoming boardwalk, perfect for a leisurely stroll, and educational venues that offer insights into the local culture. Key attractions nearby include picturesque beaches and a popular nudist beach, making it a diverse destination for sun seekers.
  • Pelican Key: Situated around the vibrant Simpson Bay, Pelican Key is a delightful neighborhood renowned for its beachside allure and outdoor activities. The area is home to luxurious resorts and lively casinos, offering a perfect blend of relaxation and entertainment. Visitors enjoy the beautiful beaches, including a nudist beach, providing a welcoming atmosphere for all. Pelican Key's proximity to Simpson Bay makes it an ideal spot for exploring local attractions while enjoying the stunning coastal views.
  • Cole Bay: Just 0.9 miles from Simpson Bay, Cole Bay is a lively city that offers a unique blend of beach life and outdoor adventures. Travelers are drawn to its scenic vistas and vibrant atmosphere, which includes a variety of educational and recreational venues. The city's boardwalk is a perfect place for a leisurely walk, while nearby beaches and a nudist beach cater to sun lovers seeking relaxation. Cole Bay serves as an excellent base for exploring the surrounding area while enjoying all the delights of island living.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 upcoming trip? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway!

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your booking. Being the planner definitely pays off! When you join our travel rewards program, One Key, you can immediately access member discounts and earn OneKeyCash™ on eligible reservations. Enroll today and begin enjoying your savings!

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board provides a convenient platform for you to plan new trips, manage your existing plans, and organize your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To discover more about Trip Boards, please 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. 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:

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

  • 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)
  • Maho Beach (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?
Simpson Bay is a fantastic choice for vacation rentals in Sint Maarten, offering a vibrant atmosphere with plenty of amenities and attractions. One of the best areas to stay in is the vicinity of Simpson Bay Beach. This area boasts a stunning stretch of sand and is known for its vibrant nightlife, with numerous bars and restaurants lining the beach. You can easily enjoy a relaxing day by the water and then transition to an exciting evening with live music and delicious local cuisine.

Another great option is the area near the Simpson Bay Lagoon, which is superb for those interested in water sports and boating. Here, you'll find a variety of rental properties, from cozy apartments to luxurious villas, with many offering picturesque views of the lagoon and the yachts that dock there. The lagoon is not only beautiful but also a gateway for sailing, making it a prime spot for marine enthusiasts.

In addition to the beaches and lagoon, Simpson Bay is close to top attractions like the Maho Beach, famous for its proximity to the airport where you can watch planes land just overhead, and the nightlife hub of Mullet Bay, known for its casinos and entertainment options. With a diverse range of vacation rentals available, including over 200 properties, you're sure to find the superb home base to explore all that this lively area has to offer.

*Please play responsibly. You must be at least 21 years old to participate in any form of gambling in the United States. If you believe you have a gambling problem, seek help from professional organizations such as the National Council on Problem Gambling at www.ncpgambling.org or call their helpline at 1-800-522-4700.
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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
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, travelers should explore the vibrant area along the coastline, particularly near the Simpson Bay Lagoon and its surrounding beaches. This locale offers a variety of vacation rentals that boast direct access to the sandy shores and picturesque views of the Caribbean Sea. Many properties in this area come with amenities such as private balconies, swimming pools, and outdoor dining spaces, great for soaking in the tropical ambiance.

The beachfront near Kim Sha Beach is particularly popular, featuring numerous vacation homes and condos that provide easy access to water sports and beach activities. Rentals here often include conveniences like beach gear, fully equipped kitchens, and air conditioning to enhance comfort during warm days. Additionally, the proximity to local restaurants and beach bars ensures that guests can easily enjoy the vibrant nightlife and culinary delights that Simpson Bay has to offer.

For those seeking a more secluded experience, consider properties located slightly away from the main tourist areas, which can offer serene surroundings with lush gardens, private pools, and stunning sunset views. This allows for a more tranquil retreat while still being within a short drive to the lively attractions of Simpson Bay. 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 about 126 available across the area. These apartments are typically located in vibrant neighborhoods close to the beach and various dining options, providing guests with easy access to the stunning coastline and local attractions. Most rooms come equipped with modern amenities, including fully equipped kitchens, spacious living areas, and often private balconies or terraces for enjoying the beautiful island views.

Condos are also a popular choice, with around 98 options available. These rentals usually offer resort-style amenities, such as swimming pools, fitness centers, and easy beach access, appealing to travelers looking for a more luxurious experience. For those seeking larger accommodations, about 73 villas can be found, featuring multiple bedrooms, private gardens, and outdoor spaces ideal for gatherings. Additionally, around 53 vacation houses and several cottages provide more home-like settings, superb for families or groups wanting a cozy retreat.
Are there any family house rentals in Simpson Bay?
In Simpson Bay, Sint Maarten, families will find a wealth of vacation rentals, with around 157 options available. This vibrant area is known for its beautiful beaches and welcoming atmosphere, making it an ideal spot for group getaways. Many properties offer spacious living areas, fully equipped kitchens superb for family meals, and outdoor spaces where children can play and adults can relax.

Visitors can enjoy amenities like private pools, game rooms, and easy access to the stunning Simpson Bay Beach. The locale is also close to attractions such as the famous Maho Beach, where the thrill of watching airplanes land can be an unforgettable experience for both kids and adults.
Can I rent a vacation home with a pool or hot tub in Simpson Bay?
In Simpson Bay, there are plenty of vacation homes available for rent that come with pools or hot tubs, with around 254 options to choose from. This lively area is known for its beautiful beaches and vibrant nightlife, making it an ideal destination for travelers seeking relaxation and entertainment.

You can find rental properties in neighborhoods like Pelican Key and Beacon Hill, which are popular for their proximity to the beach and stunning ocean views. Many of these homes feature private pools and hot tubs, outdoor dining areas, and spacious living spaces, superb for families or groups looking to unwind after a day of exploring.

Amenities such as fully equipped kitchens, air conditioning, and Wi-Fi are common, ensuring a comfortable stay. 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. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Simpson Bay?
In Simpson Bay, travelers can find a variety of pet-friendly house rentals that cater to different preferences and group sizes. With 61 options available, visitors can expect amenities such as private pools, outdoor terraces, and fully equipped kitchens, offering a comfortable stay for both pets and their owners. Many properties provide spacious living areas and easy access to outdoor spaces, making them ideal for pets to roam and enjoy the beautiful surroundings.

The Simpson Bay area is also known for its vibrant atmosphere, with nearby beaches and waterfront activities. While exploring, pet owners can enjoy the scenic views along the beach and take leisurely walks in the area. The proximity to local restaurants and shops adds to the convenience, ensuring that both travelers and their pets have a satisfying stay.
Are there any remote work vacation rentals in Simpson Bay?
In Simpson Bay, Sint Maarten, there are plenty of options for remote work vacation rentals, with around 240 available. This vibrant area is known for its beautiful beaches and lively atmosphere, making it an excellent choice for those looking to balance work and leisure. Many properties in the vicinity come equipped with essential remote work amenities such as high-speed Wi-Fi, dedicated workspaces, desks, and comfortable office chairs. Some rentals even include additional features like safe work environments, computer monitors, and laptop workstations to enhance productivity.

Travelers can expect a range of accommodations, from modern condos with ocean views to spacious villas that offer more privacy. The area is conveniently located near popular points of interest, including the famous Maho Beach and numerous restaurants, shops, and entertainment options, ensuring that after a day's work, there are plenty of opportunities to relax and explore. 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 travelers 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 vacation rental amenities include WiFi, which is essential for travelers looking to stay connected. Most rentals come equipped with a kitchen, allowing guests to prepare their own meals, and many feature pools for relaxation and recreation. Additionally, you'll often find coffee and tea makers, as well as blenders, ensuring that guests can easily enjoy their morning beverages or whip up smoothies.
When is the best time to visit Simpson Bay for a vacation rental?
September is the most popular time to visit Simpson Bay, offering a delightful blend of warm weather and vibrant local culture. This month falls within the peak travel season from July to September, which attracts visitors seeking sun-soaked beaches and lively nightlife. With average temperatures ranging from the mid-70s to mid-80s Fahrenheit, it's an ideal time for outdoor activities such as snorkeling, sailing, or simply lounging on the beach.

During this peak season, travelers can engage in the island's rich offerings, from delicious dining to exhilarating water sports. The lively atmosphere is great for those looking to socialize and engage with other vacationers.

For those who prefer a quieter experience while still enjoying pleasant weather, consider visiting in October. This month marks the transition into the low season, allowing you to benefit from lower rental rates and fewer crowds. October still offers comfortable temperatures and the chance to explore the natural beauty of the island at your own pace.

Ultimately, the best time to visit Simpson Bay hinges on whether you seek the vibrant energy of peak season or the tranquility of early fall.
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, travelers will find a variety of attractions that highlight the beauty and charm of Sint Maarten. The Simpson Bay Lagoon is a great feature, offering stunning views of yachts and sailboats, making it a great spot for those interested in water activities. Nearby, the Maho Beach area is famous for its great experience of watching planes land just above the beach, providing a thrilling spectacle for visitors.

For nightlife and dining, the area boasts a vibrant selection of beach bars and restaurants along the waterfront, where guests can enjoy fresh seafood and local cuisine.
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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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