Discover a selection of 2,500 vacation rentals in Simpson Bay, SX that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $110 per night, and houses and villas are popular options for a stay in Simpson Bay. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Simpson Bay
Destination guide

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.

Things to do

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:

  • Cuisinart Resort Golf Course (9.8 mi / 15.8 km)
  • Mullet Bay Golf (1.6 mi / 2.6 km)

Seasonal weather averages in Simpson Bay

If you're hoping to enjoy some warm-weather activities on your vacation, June, July, September and October are the hottest months to visit, when temperatures average 84°F.

Natural features

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:

  • Simpson Bay Beach (0.5 mi / 0.8 km)
  • Flamingo Beach (0.6 mi / 0.9 km)
  • Maho Beach (1.6 mi / 2.6 km)
  • Maho Bay (1.7 mi / 2.7 km)
  • Mullet Bay Beach (2 mi / 3.3 km)
  • Little Bay Beach (2.7 mi / 4.3 km)
How to get there

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.

What are the top vacation rentals in or near Simpson Bay?

Whether you're searching for a cozy retreat for you and your special someone or a sprawling house to fit the family, you'll find some top vacation rentals in and around Simpson Bay. Here are a couple to get your inspiration flowing:

  • "Oasis@the Cliff: Beachfront Luxury Experience" is a guest favorite. Around 2 miles from Simpson Bay, it has 2 bedrooms and loads of amenities to help you feel at home, including a blender and shopping.
  • Alternatively, make yourself comfortable at "Luxury, Gated Estate, Oceanside". Located around 4 miles from the heart of Simpson Bay, it has 4 bedrooms and comes with a garden and towels.

For even more great options, use the search bar at the top of the page to find the perfect Simpson Bay vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Simpson Bay?

We all deserve to slow down and take a break occasionally. If you're yearning for a couple of mornings in bed with a good book and a steaming coffee, you'll find some fabulous weekend getaways in and near Simpson Bay. Check out two of our favorites:

  • Get comfy at "We Are Rebuilt And Better Than Ever Gorgeous Come Back To Paradise". Around 5 miles to the east of Simpson Bay, this cozy escape has all you need for a chilled out stay, including a balcony and a stovetop.
  • Or, throw a few clothes in a bag and head to "Beachfront Villa Lavinia #9 On Great Bay". This sought-after getaway is around 3 miles east of Simpson Bay and comes with coffee and tea making facilities and off-street parking options.

Can I find studio apartments for rent in and around Simpson Bay?

Absolutely! If you'd like a simple yet stylish stay, you can't top a studio apartment. These compact properties ooze charm and are often conveniently positioned in the center of town. Take a look at the following options in or near Simpson Bay:

  • One of our favorite properties is "Pure Beach Apartment". Lock in a few nights or longer at this popular stay and you'll have access to air conditioning and cable/satellite TV services.
  • "Second Home Beach Apartment" is another top stay, providing all you need for the perfect Simpson Bay vacation. Useful amenities here include a hair dryer and a nearby marina.

Can I find short term rentals in or near Simpson Bay?

Short-term rentals are in good supply in and around Simpson Bay. Stay for a night or two in a cool condo, a resort-style apartment or a large home. Whatever type of property you're looking for, you'll find what you need with Vrbo. Here are a few top picks:

  • If you'd like to be close to the action, "Ppl. Directly On Beach" will be just the thing. It's within easy reach of the center of Simpson Bay and an excellent base to check out attractions like Maho Beach and Mullet Bay Beach.
  • Leap out of bed, make some breakfast and then plan what to see around "Beach Front Lovely Spacious 2bedroom 2. 5 Bath Simpson Bay - The Sandcastle". American University of the Caribbean and Guana Bay Beach should be on your itinerary if you stay at this short-term rental.

What are the best romantic weekend getaways in or near Simpson Bay?

Whether spent in a cabin, an apartment or a lodge, a romantic weekend getaway is a fantastic way to spice up your relationship. Whisk your sweetie off for a couple of leisurely days at one of these top escapes in or near Simpson Bay:

  • Sneak off on Friday for a few nights of passion at "Oasis@the Cliff: Beachfront Luxury Experience". Located approximately 2 miles from Simpson Bay, this property comes with lots of nice touches, including a resort and beauty services.
  • "Luxury, Gated Estate, Oceanside" is another wonderful option that's sure to impress. It's around 4 miles from Simpson Bay and comes with massage services and air conditioning.

What are the best large group vacation rentals in or near Simpson Bay?

Big groups mean gigantic fun. They also mean finding a place that'll easily fit your whole crew. Browse our large group vacation rentals in or around Simpson Bay and get your loved ones together under the one roof:

  • A wide array of amenities including a beach view and a kitchen make "We Are Rebuilt And Better Than Ever Gorgeous Come Back To Paradise" a standout. This popular getaway has 5 bedrooms and accommodates up to 12 guests. From the heart of Simpson Bay, it's around 5 miles away to the east.
  • Invite up to 16 of your friends to "Pristine 7 - Suite Villa With Ocean Views + Pool And Bbq" and fill its spaces with laughter and love. This popular option has 7 bedrooms and is around 1 mile to the south of Simpson Bay. It's crammed with features to keep your group comfortable, including a water view and mountain views.

What are the best houses for rent with a pool in or near Simpson Bay?

A pool is often an all-important amenity when deciding where to spend your vacation, especially if you're getting away with the kids. Check out these houses with a pool in or near Simpson Bay and spend your days splashing about:

  • Get comfortable at "1 Beach House On The Ocean With Private Pool", where your top priority will be chilling by the pool. Amenities including on-site watersports and a living room help make this retreat a guest favorite.
  • Spend laid-back days splashing about or finding some peaceful moments by the water at "La Madrague, Cosy House With Private Pool Few Steps To The Beach". This vacation rental is also a firm favorite and offers a barbecue grill, a smart TV and more.

Simpson Bay has a tropical savanna climate, with average summertime temperatures hovering between 80 ºF and 80 ºF. But you don't have to wait until summer to visit! Take a look at the search bar at the top of the page and adjust the filters to find the perfect Simpson Bay vacation rental and organize your getaway for any time of year.

What are the best large family vacation rentals in or near Simpson Bay?

Whether you're traveling with the kiddos or you're taking all your relatives along, family vacations spell fun. These large rentals in and around Simpson Bay have space for everyone — along with everything you need to keep them all happy:

  • Approximately 4 miles east of Simpson Bay, "Luxury Oceanside Estate" has 4 bedrooms and can sleep up to 10 guests. Amenities here include a stair gate and a garden.
  • "We Are Rebuilt And Better Than Ever Gorgeous Come Back To Paradise", around 5 miles to the east of central Simpson Bay, was also made for family getaways. As many as 12 of your loved ones can fit into this welcoming property which features 5 bedrooms, nearby ecotour services, a microwave oven and more.

As tempting as it may be, don't spend your entire vacay kicking back indoors. Head out and explore some nearby family-friendly attractions, starting with Sint Maarten Park.

What are the best large houses to rent with indoor pools in or near Simpson Bay?

Add some grandeur to your vacation by booking a place with a private indoor pool. These gorgeous large houses in or near Simpson Bay have a swimming space that's your very own, along with tons of room for whoever you're bringing with you:

  • Unpack your bags at "Alma - Direct Oceanfront - Luxury 4 Bedrooms Private Villa" and while away your days poolside. This sprawling retreat has 4 bedrooms that sleep up to 8 guests and a range of other impressive amenities. A chef and a kitchen are among them.
  • Another outstanding property is "Paradise View - New". With 6 bedrooms sleeping up to 12 people, you can invite your entire crew to stay with you and swim. A swimming pool and a beach view are other amenities your guests can make use of here.

Want to see a few more options? Find your dream pad by using the search bar at the top of the page. Simply adjust the filters to find the Simpson Bay vacation rental that's perfect for you.

Are there vacation rentals with hot tubs in or near Simpson Bay?

Along with having a host of health benefits, immersing yourself in a hot tub simply feels outrageously good. If it's about time you indulged yourself, these vacation rentals in and around Simpson Bay offer this luxurious perk and more:

  • Stay at "3 - Gold Coast Paradise Studio" and it could be difficult to drag yourself away from those warm, bubbly waters. Also make use of other amenities such as a beach view and a resort.
  • "9 - Sint Maarten Blue Pearl Studio" is another traveler favorite where you can take a piping hot plunge. It comes with other luxe amenities too, like a resort and a spa tub.