Simpson Bay holiday rentals

We found 3,235 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Simpson Bay by choosing from 42 houses, 171 apartments and other holiday rentals. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for hanging out with the people that matter most, which might include a garden and hot tub. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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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 holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Simpson Bay

Are you searching for things to do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Simpson Bay has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 an active traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Simpson Bay. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • 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 holiday, September, August, October and July are the hottest months to visit, when temperatures average 28°C.

Transport to and around Simpson Bay

The nearest airport is in Philipsburg (SXM-Princess Juliana Intl.), located 1.1 mi (1.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could 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 holiday rental?
When considering a holiday rental in Simpson Bay, Sint Maarten, the Simpson Bay area itself is an excellent choice for a delightful stay. This vibrant neighbourhood is known for its stunning beachfront, making it an ideal spot for sun-seekers and water sports enthusiasts alike. With a variety of properties available, from charming villas to modern apartments, visitors can find something to suit their preferences.One of the top attractions in the area is the beautiful Simpson Bay Beach, where you can relax on the soft sands or partake in various water activities such as snorkelling and jet skiing. Additionally, the lively option of the Simpson Bay Marina offers a range of dining options and boutique shops, providing a superb blend of relaxation and entertainment.For those looking to explore further, the nearby Maho Beach is famous for its proximity to the airport, where you can witness planes landing just above your head—an experience that is both thrilling and unforgettable.
Where are the best areas for renting a beach house in Simpson Bay?
For renting a beach house in Simpson Bay, the area along the beachfront offers stunning views and easy access to the sandy shores. The stretch near the Simpson Bay Lagoon is particularly popular, where travellers can find a variety of beachfront properties, including modern villas and charming bungalows. Many of these rentals come equipped with amenities such as private pools, outdoor patios for al fresco dining, and fully equipped kitchens, making them ideal for families or groups looking to enjoy a relaxing beach holiday.Additionally, properties in the vicinity of the Simpson Bay Beach offer convenient access to local shops, restaurants, and vibrant nightlife, adding to the appeal for those seeking both relaxation and entertainment. Many accommodations also feature water sports facilities, allowing guests to partake in activities like kayaking and paddleboarding right from their doorstep.Nearby, the Maho Beach area is known for its lively option and proximity to the famous airplane landing views. Beach houses here often include outdoor lounges and easy beach access, great for enjoying the sun and sea.
What is the most popular type of holiday rental accomodation in Simpson Bay?
In Simpson Bay, the most popular type of holiday rental accommodation is apartments, with around 684 available in the area. These apartments are typically situated in lively neighbourhoods close to the beach and local amenities, offering guests the convenience of fully equipped kitchens, comfortable living spaces, and often stunning views of the Caribbean Sea. Many of these units also include balconies or terraces, great for enjoying the tropical surroundings.Condos are another prevalent choice, with approximately 392 options available. These condos frequently provide resort-style amenities such as pools, fitness centres, and easy access to the beach, making them ideal for travellers seeking a more luxurious experience.For those looking for more spacious rooms, there are about 244 villas available, which come with private gardens, outdoor seating areas, and multiple bedrooms. These villas are great for families or groups wanting to have a more secluded stay while still being close to the vibrant setting of Simpson Bay. Lastly, there are around 108 holiday houses that offer a homely feel with ample living space and the convenience of self-catering facilities.
Are there any family house rentals in Simpson Bay?
In Simpson Bay, Sint Maarten, there is a wealth of family-friendly house rentals available, with around 143 options to choose from. This vibrant locale is well-known for its stunning beaches and lively option, making it an ideal destination for families. Many properties boast spacious living areas, fully equipped kitchens, and outdoor spaces where children can play, ensuring comfort and convenience for all guests.Visitors can enjoy easy access to nearby attractions such as the beautiful Maho Beach, famous for its unique proximity to the airport, and the lively Simpson Bay Beach, great for sunbathing and water sports. Additionally, the area is dotted with restaurants and shops, offering a taste of local culture and cuisine.
Can I rent a holiday home with a pool or hot tub in Simpson Bay?
In Simpson Bay, Sint Maarten, there are plenty of holiday homes available for rent that come with pools and hot tubs, with around 262 options to choose from. This beautiful area is renowned for its stunning beaches and vibrant setting, making it a popular destination for travellers seeking relaxation and fun in the sun.Many of the rentals in Simpson Bay offer amenities such as private swimming pools, inviting hot tubs, spacious outdoor terraces, and fully equipped kitchens, ideal for families or groups looking to enjoy a luxurious getaway. Some properties may also feature additional conveniences like barbecue areas, lush gardens, and easy access to the nearby beach, enhancing the overall holiday experience.
Are there pet-friendly house rentals in Simpson Bay?
In Simpson Bay, there is a variety of pet-friendly house rentals available, with over 60 options to choose from. This area is known for its stunning beaches and vibrant setting, making it an ideal destination for travellers looking to bring their furry companions along. Many of the holiday rentals in Simpson Bay come equipped with amenities such as private pools, outdoor terraces, and fully equipped kitchens, suiting the needs of families or groups seeking comfort and convenience during their stay.Simpson Bay itself is close to several pet-friendly points of interest, including beautiful stretches of beach where pets can enjoy the sun and surf. The nearby Mullet Bay Beach is also a popular spot for pet owners, offering expansive sandy areas and calm waters. Additionally, the local eateries and cafes often have outdoor seating options that welcome pets, allowing for a pleasant dining experience with your four-legged friends.
Are there any remote work holiday rentals in Simpson Bay?
In Simpson Bay, Sint Maarten, there is an abundance of remote work-friendly holiday rentals, with around 940 options available. This picturesque area is known for its stunning beaches and vibrant nightlife, making it an ideal destination for those looking to blend leisure with productivity. Many properties come equipped with high-speed Wi-Fi, ensuring seamless connectivity for work-related tasks.Travellers can expect to find a range of amenities designed to enhance their remote working experience, including dedicated workspaces, comfortable seating, and some even offer additional services like limo or town car transportation for easy commutes. The proximity to local cafes and restaurants also provides convenient spots for meetings or a change of scenery. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Simpson Bay?
In Simpson Bay, popular rental amenities include well-equipped kitchens, which allow guests to prepare their own meals, alongside onsite parking for convenience. Many properties also feature coffee and tea makers, ideal for morning brews before heading out to explore the nearby beaches. Balconies and patios are common, providing lovely outdoor spaces to relax and enjoy the tropical surroundings.
When is the best time to visit Simpson Bay for a holiday rental?
The best time to visit Simpson Bay for a holiday rental is during the peak season from July to September. This period is particularly popular among travellers seeking a vibrant setting with plenty of activities. The warm Caribbean climate, with temperatures typically ranging from 25 to 30 degrees Celsius, makes it an ideal time for beach outings, water sports, and exploring the stunning coastline.September is a noteworthy month for visitors, as you can enjoy the tail end of the peak season with slightly fewer crowds compared to July and August. The festive ambience continues, and you can partake in local events while soaking up the sun on beautiful beaches or indulging in the delightful culinary scene.For those looking for a more budget-friendly option, consider visiting in October, when the prices for holiday rentals tend to drop. This transitional period offers a chance to experience the tranquility of Simpson Bay, as fewer tourists mean that you can enjoy your surroundings more peacefully. You can still enjoy pleasant weather and have the opportunity to explore the island's exquisite nature without the busyness of peak season.
What are the top attractions in Simpson Bay?
In Simpson Bay, visitors can enjoy a variety of attractions that highlight the area's vibrant culture and stunning natural beauty. The picturesque Simpson Bay Beach is a major draw, offering soft sands and clear waters, superb for sunbathing or swimming. Close to the beach, you'll find lively beach bars and restaurants where you can sample local cuisine and refreshing cocktails.The Marina at Simpson Bay is another key attraction, where travellers can admire luxury yachts and enjoy waterfront dining. For those interested in nightlife, the area boasts a range of bars and clubs that cater to different tastes, ensuring a lively option after sunset.Nearby, the Maho Beach area is famous for its dramatic plane landings, providing a great experience for aviation enthusiasts and beachgoers alike. Additionally, the nearby Simpson Bay Lagoon offers opportunities for water sports, including kayaking and paddleboarding, making it a great spot for adventure seekers.For a taste of local culture, the nearby island's capital, Philipsburg, is easily accessible and features historical sites, shopping areas, and the vibrant Front Street.
Are all fees included in the Simpson Bay holiday homes prices shown on Stayz?
Stayz 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.
Are there any Simpson Bay holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Simpson Bay holiday homes?
You can find great discounts on holiday homes in Simpson Bay on Stayz, 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.
Can I change or cancel my Simpson Bay holiday home booking on Stayz?
To find Simpson Bay holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Simpson Bay?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Simpson Bay holiday home?
Book your Simpson Bay holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Simpson Bay?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Simpson Bay to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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