Simpson Bay vacation rentals

We found 3,231 vacation rentals — enter your dates for availability

Welcome to the enchanting shores of Simpson Bay, where stunning beaches meet vibrant island culture. Bask in the sun on the golden sands of Simpson Bay Beach or embark on outdoor adventures in the nearby Seaside Nature Park. With an array of luxurious resorts, cozy condos, and breathtaking villas, this destination caters perfectly to families and groups seeking comfort and convenience. Experience the warmth of local cuisine and the charm of nearby neighborhoods, all while enjoying the spacious amenities and home-like atmosphere that vacation rentals offer. Your idyllic getaway awaits!

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Find out more about Simpson Bay

Why visit Simpson Bay

  • Stunning Beaches: Enjoy the beautiful sandy shores of Mullet Bay Beach, perfect for sunbathing and romantic getaways.
  • Outdoor Adventures: Ideal for outdoor enthusiasts, Simpson Bay offers a range of activities amidst lush parks and scenic views.
  • Family-Friendly Atmosphere: The charming village of Simpson Bay is perfect for family excursions and creating lasting memories.
  • Luxurious Accommodations: Choose from a variety of vacation rentals, including the Simpson Bay Resort and Beach Resort for a relaxing stay.
  • Vibrant Local Culture: Experience the local vibe with beach bars and outdoor swimming pools, enhancing your vacation experience.

Popular types of accommodation in Simpson Bay

Planning a getaway to Simpson Bay? You've picked a fantastic destination. Explore a variety of vacation rentals, including condos, villas, and apartments, that cater to your every need. Enjoy the stunning Simpson Bay Resort or unwind at the Simpson Bay Beach Resort, where you can sip drinks at beach bars and take a dip in outdoor swimming pools. Your perfect vacation experience awaits.

  • Condos: A top choice for visitors, condos offer a blend of comfort and convenience with stunning views and easy access to the beach.
  • Villas: Luxurious villas provide spacious accommodations, perfect for families or groups seeking privacy and relaxation.
  • Apartments: Ideal for travelers looking for affordable yet comfortable options, apartments offer a home-like atmosphere.
  • Houses: These homes offer a unique local experience, perfect for families or friends traveling together.
  • Guest Houses: A charming and budget-friendly option, guest houses provide a more personal touch to your stay.**

Top attractions in and around Simpson Bay

Simpson Bay offers a perfect getaway for beach lovers and outdoor enthusiasts. With stunning beaches and beautiful parks, this destination is ideal for families looking to enjoy a scenic vacation. Whether you're exploring the sandy shores or relaxing in the lush surroundings, there are plenty of attractions to keep you entertained. Be sure to take advantage of the local points of interest that highlight the natural beauty of Sint Maarten.

  • Simpson Bay Beach: A stunning beach nestled in Simpson Bay, known for its soft sand and vibrant beach vibes, making it perfect for sunbathing and water activities.
  • Seaside Nature Park: Located a mile from Simpson Bay, this eco-friendly park offers outdoor adventures for families, including hiking trails, bird watching, and lush scenery.
  • Kim Sha Beach: Another beautiful beach in Simpson Bay, Kim Sha Beach is famous for its lively atmosphere, ideal for swimming and enjoying beachside dining.

Things to do recommended for couples

For a romantic getaway in Simpson Bay, stroll along the Philipsburg Boardwalk. Located 3 miles away, this beautiful spot offers beach vibes and picturesque views, perfect for couples to enjoy a leisurely walk or a cozy dinner by the water.

Things to do recommended for families

Families can explore the excitement of Rainforest Adventures St. Maarten, a recreation park just 2 miles from Simpson Bay, offering wellness and relaxation vibes suitable for all ages. Enjoy thrilling activities while soaking in the beautiful surroundings together.

Things to do recommended for groups

Experience the thrill of golfing at Mullet Bay Golf, just 2 miles from Simpson Bay, or explore the vibrant Front Street District and Harbour Point Village for shopping, both located 4 miles away. Perfect for group travelers seeking local vibes and activities.

*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 traveling with friends, family, pets, or planning an extended stay, be sure to use the appropriate filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Simpson Bay with a group: Think about how many bedrooms you'll require, as well as any additional features like a full kitchen or outdoor space for group gatherings. The good news is that you can easily filter for all of these options and more on Vrbo.
  • Traveling to Simpson Bay with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Simpson Bay: For many families, a vacation isn’t truly fulfilling without their furry companion by their side. If you can relate, be sure to explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all family members feel comfortable and at home.
  • Planning for a long term stay visiting Simpson Bay: If you're searching for 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 rental options. 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, is a tropical paradise perfect for beach lovers and outdoor enthusiasts. With its stunning sandy beaches, including the renowned Mullet Bay Beach, visitors can soak up the sun and enjoy romantic vibes. The nearby village of Simpson Bay offers a charming atmosphere, ideal for family-friendly excursions and scenic views. Whether you're looking for relaxation or adventure, Simpson Bay has something for everyone to explore and cherish during your vacation.

  • Cole Bay: Located a mere 0.9 miles from Simpson Bay, Cole Bay is a vibrant city that offers a perfect blend of beach, outdoor, and scenic experiences. Visitors flock to this area for its stunning views and relaxing atmosphere. Here, you’ll find a variety of activities and venues including educational opportunities, luxurious resorts, and a picturesque boardwalk. Local attractions such as the beautiful beach, a nudist beach, and the serene bay make Cole Bay an ideal spot for sunbathing, swimming, and enjoying water sports.
  • Beacon Hill: Nestled within the Simpson Bay area, Beacon Hill is a charming village known for its beautiful beaches and outdoor scenery. This neighborhood is a favorite among travelers who seek to unwind in a tranquil environment. Beacon Hill boasts an array of activities such as educational experiences, luxurious resorts, and scenic boardwalks. The proximity to local landmarks, including pristine beaches, a nudist beach, and the inviting bay, ensures that visitors can enjoy sun-soaked days and stunning sunsets.
  • Pelican Key: Pelican Key, situated around Simpson Bay, is a delightful neighborhood famous for its breathtaking beaches and outdoor adventures. Travelers are drawn to this area for its scenic beauty and engaging activities. Popular attractions in Pelican Key include upscale resorts, educational venues, and a lovely boardwalk. With local highlights such as the captivating beaches, a nudist beach, and the tranquil bay, this neighborhood offers a perfect getaway for relaxation and exploration.

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 simple

Are you hoping to save money on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to narrow down your options by price, location, and type of vacation rental. We're here to help you find the perfect place for your next adventure.

Vrbo Trips: Planning made easy

Vrbo's Trip Board is a fantastic tool that allows you to plan and manage your travel experiences seamlessly. You can easily create new trips, pick up right where you left off, or organize and review your existing plans. All the properties you've saved or booked can be conveniently accessed in the sections for Potential, Upcoming, or Current Trips. To make the most of the Trip Boards, simply visit: https://www.vrbo.com/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:

  • Maho Beach (1.6 mi / 2.5 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)
  • St. Martin Beaches (1.7 mi / 2.8 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, Sint Maarten when booking a vacation rental?
When considering the best area to stay in Simpson Bay, Sint Maarten for a vacation rental, the Simpson Bay area itself is a fantastic choice. This vibrant neighborhood is known for its beautiful beaches and lively option, making it superb for both relaxation and entertainment. One of the highlights of Simpson Bay is its stunning beach, where you can enjoy sunbathing, swimming, and water sports. Additionally, the area boasts a variety of waterfront restaurants and bars, providing a great selection of dining and nightlife options.In terms of attractions, the nearby Simpson Bay Lagoon is a must-see, as it's one of the largest natural harbors in the Caribbean and offers an array of water activities. The proximity to the airport also makes it convenient for travelers. With numerous vacation rentals available in the area, visitors can find everything from cozy studios to luxury villas, ensuring a comfortable stay that suits their needs.
What are the most popular vacation rentals in Simpson Bay?
Vacation rentals in Simpson Bay are most commonly found as apartments, condos, and villas, offering guests a range of choices for their stay. Apartments are the most prevalent, with over 160 available, followed by over 100 condos and more than 60 villas. These property types are popular for their space, privacy, and amenities, often accommodating families and groups. You'll find a high concentration of these popular rentals in areas like Pelican Key and Maho, which are favored for their proximity to beaches and local attractions.
What amenities do vacation rentals in Simpson Bay usually offer?
Vacation rentals in Simpson Bay typically offer a wide range of amenities to enhance your stay. You'll often find fully equipped kitchens, air conditioning, and Wi-Fi, ensuring comfort and convenience. Many properties also provide parking, laundry facilities, and private balconies or terraces where you can enjoy the tropical breeze. For relaxation, pools are a common feature, and some rentals boast ocean views, allowing you to soak in the stunning coastal scenery.
Are there family-friendly vacation rentals in Simpson Bay?
Yes, Simpson Bay offers over 140 family-friendly vacation rentals, making it easy to plan a trip with loved ones. You'll find many condos, villas, and apartments designed to accommodate families. Pelican Key is a popular area for families, with over 70 family-friendly properties. These rentals often come with amenities like fully equipped kitchens for preparing meals, laundry facilities for longer stays, and high chairs or travel cribs for younger guests, ensuring a comfortable and convenient experience for everyone.
Are there pet-friendly vacation rentals in Simpson Bay?
Yes, Simpson Bay has over 60 pet-friendly vacation rentals, so you can bring your furry companions along. Condos, villas, and apartments are common property types that welcome pets. You'll find a good selection of pet-friendly options in Maho and Pelican Key, with over 20 properties in each area. These rentals often feature amenities like secured yards for pets to play safely and easy-clean floors, making your stay with pets more enjoyable.
What are the best areas for group vacation rentals in Simpson Bay?
For groups traveling to Simpson Bay, you'll find over 50 vacation rentals designed to accommodate larger parties. Pelican Key is an excellent choice, offering over 25 large group rentals, while Maho also provides over 15 options. These areas feature spacious villas, houses, and larger condos that are perfect for friends or extended family. Many group-friendly rentals include multiple bedrooms and bathrooms, large dining areas for shared meals, fully equipped kitchens, and ample parking for several vehicles, ensuring everyone has space and comfort.
What are the best luxury vacation rentals in Simpson Bay?
Simpson Bay offers over 230 luxury vacation rentals for those seeking an upscale experience. Pelican Key is a prime area for luxury, with over 60 high-end properties, and Maho also features over 30 luxury rentals. You'll often find exquisite villas and houses in these areas. These premium rentals frequently boast amenities such as private pools, stunning ocean views from spacious balconies, and hot tubs, providing an indulgent and relaxing retreat.
Are there any budget-friendly vacation rentals in Simpson Bay?
Yes, Simpson Bay provides over 100 budget-friendly vacation rentals, offering great value for your trip. Pelican Key is a top spot for value, with over 50 budget-friendly properties, and Maho also has over 20 options. Apartments and condos are common property types that provide excellent value. These rentals often come with full kitchens, allowing you to save on dining out, and laundry facilities, which can be a cost-saver for longer stays. Choosing a vacation rental also means groups can split costs, making your trip more affordable.
Are there any vacation rentals in Simpson Bay with a pool?
Yes, Simpson Bay has over 280 vacation rentals that feature pools, perfect for enjoying the tropical climate. You'll find many apartments, condos, and villas offering pool access. Pelican Key is a popular area for rentals with pools, boasting over 110 properties, and Maho also has over 30 options. These rentals often provide outdoor pools for soaking up the sun, private pools for enhanced privacy, and some even offer heated pools for year-round enjoyment.
Are there any vacation rentals in Simpson Bay with a hot tub?
Yes, Simpson Bay offers over 30 vacation rentals equipped with a hot tub, providing a relaxing amenity for your stay. Condos, apartments, and villas are common property types that feature hot tubs. Pelican Key is a great area to find these, with over 20 rentals offering hot tubs, and Maho also has several options. Many hot tubs are private and located outdoors, allowing you to unwind under the stars or enjoy scenic views.
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, vacation rentals commonly feature a range of desirable amenities that enhance the travel experience. Most properties include a fully equipped kitchen, allowing guests to prepare their own meals and enjoy dining in. Onsite parking is typically available, making it convenient for those with rental cars or personal vehicles. Many rentals also come with a coffee and tea maker, great for starting the day with a warm beverage.Additionally, guests can expect outdoor spaces such as balconies, decks, or patios, where they can relax and take in the beautiful surroundings.
When is the best time to visit Simpson Bay for a vacation rental?
The best time to visit Simpson Bay for a vacation rental is during September, just as the peak season begins to wind down. This month offers a sweet spot for travelers looking to enjoy the stunning beaches and vibrant nightlife while experiencing fewer crowds. With temperatures typically ranging from the mid-70s to low 90s Fahrenheit, September provides warm and inviting weather, great for lounging on the beach or exploring the local shops and restaurants.During the peak season from July to September, Simpson Bay attracts a bustling crowd, making it an ideal time for those eager to engage in lively activities and social events. Whether you're interested in water sports, beach parties, or simply soaking up the sun, you'll find plenty of options to keep you entertained.For travelers seeking a more budget-friendly option, consider visiting in October. This time marks the transition into the quieter low season, allowing you to enjoy the beauty of Simpson Bay with lower rental rates and a more relaxed atmosphere. The weather remains pleasant, and you can still partake in many enjoyable outdoor activities without the hustle and bustle of peak season.
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, Sint Maarten?
In Simpson Bay, visitors can enjoy a variety of attractions that showcase both the natural beauty and vibrant culture of the area. The stunning Simpson Bay Beach is a major highlight, offering soft sands and clear waters, great for sunbathing and water sports. Nearby, the picturesque Maho Beach is famous for its proximity to the airport, where travelers can watch planes land just overhead, creating a great experience.For a taste of local culture, the Simpson Bay area features a lively nightlife scene with numerous bars and restaurants along the waterfront, many of which offer fresh seafood and Caribbean cuisine. The nearby Simpson Bay Lagoon is also a must-see, known for its beautiful yachts and scenic views, making it a great spot for a leisurely stroll or boat tour.Additionally, for those interested in shopping, the area boasts various boutiques and souvenir shops, particularly around the Marina.
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 cabin or a beach condo, 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 as applicable. 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively. Vrbo also offers support via live chat through our Help Center, 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 organizing 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.

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