Simpson Bay vacation rentals

We found 3,238 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Simpson Bay by choosing from 65 houses, 131 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.
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Find out more about Simpson Bay

Find out more about Simpson Bay

Why visit Simpson Bay

  1. Stunning Beaches: Simpson Bay boasts beautiful beaches perfect for relaxation and family outings, offering breathtaking ocean views.
  2. Outdoor Activities: The area is ideal for various outdoor experiences, making it a great destination for adventure seekers.
  3. Charming Accommodations: Choose from a range of vacation rentals including condos and villas that blend luxury and comfort.
  4. Vibrant Neighborhoods: Explore lively areas like Indigo Bay, showcasing local culture and attractions.
  5. Perfect for Getaways: Whether romantic or family-oriented, Simpson Bay is an idyllic spot for memorable vacations.

Popular types of accommodation in Simpson Bay

Discover the charm of vacation rentals in Simpson Bay, where you can choose from a variety of accommodations including condos, villas, and apartments. Whether you're planning a family getaway or a romantic escape, Simpson Bay vacation rentals offer the perfect home base for your adventures. Enjoy the transparency, savings, and reassurance that come with our platform as you explore the stunning surroundings of this beautiful destination.

  • Condos: The top choice for vacation rentals in Simpson Bay, offering modern amenities and stunning views, ideal for couples or small families.
  • Villas: A luxurious option for those seeking spacious accommodations, perfect for groups or families wanting a private getaway.
  • Apartments: A versatile and budget-friendly choice, ideal for travellers wanting a home-like atmosphere close to local attractions.
  • Houses: Great for families or groups, these homes provide a secluded environment with ample space for relaxation.
  • Cottages: A charming option for a quaint and cozy stay, perfect for couples or solo travellers looking for peace.**

Top attractions in Simpson Bay

Simpson Bay is an ideal destination for those seeking a beach and outdoor vacation, offering stunning scenery and various attractions. Visitors can enjoy the beautiful beaches and parks, perfect for family outings and outdoor experiences. Whether you're looking to relax by the water or explore local points of interest, Simpson Bay provides a range of activities to make your vacation memorable.

  1. Maho Beach: Renowned for its stunning views and vibrant beach vibes, Maho Beach is famous for its unique proximity to the airport, where you can watch planes fly overhead just metres away from the shoreline.
  2. Seaside Nature Park: This eco-friendly park offers a family-friendly atmosphere with outdoor activities such as hiking and wildlife observation, making it perfect for nature lovers and families looking to explore.
  3. Simpson Bay Beach: Located right in Simpson Bay, this beautiful beach boasts soft sands and inviting waters, ideal for sunbathing, swimming, or simply relaxing by the sea.

Things to do recommended for couples

For a romantic getaway in Simpson Bay, take a leisurely stroll along the Philipsburg Boardwalk, just 4.8km away. Embrace the beach vibes and enjoy scenic views while creating unforgettable memories with your partner. It's the perfect spot for a cozy evening together.

Things to do recommended for families

Families visiting Simpson Bay can experience the excitement of Rainforest Adventures St. Maarten, a recreation park located 3.2km away. With wellness and relaxation vibes, it offers a perfect blend of adventure and tranquility for all ages, ensuring a memorable family vacation.

Things to do recommended for groups

Experience the thrill of the Hollywood Casino or Casino Royale, both offering vibrant city vibes and romance. For outdoor enthusiasts, Mullet Bay Golf is just a couple of miles away, perfect for a day on the greens with your friends.

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

When planning your trip, whether you’re travelling with a group, spending time with family, bringing along your pets, or seeking extended stays, it's important to apply the right filters based on your priorities. 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, as well as amenities like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Simpson Bay with young kids: Traveling with young children can present its challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is a wise approach.
  • Taking your pets with you to Simpson Bay: For many families, a getaway isn't truly fulfilling without their furry companions. If this resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Simpson Bay: If you're in search of vacation rentals offering 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 options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Simpson Bay

Simpson Bay, with its stunning ocean views and beautiful beaches, offers an unforgettable vacation experience. Ideal for romantic getaways or family-friendly excursions, you can explore vibrant neighborhoods like Indigo Bay. Enjoy beach condos that provide easy access to the picturesque shoreline, or relax in charming accommodations that perfectly blend luxury and comfort. Whether you seek adventure or relaxation, Simpson Bay is the perfect destination for your tropical escape.

  • Beacon Hill: Nestled in the picturesque area of Simpson Bay, Beacon Hill is a charming village that offers a delightful blend of beach and outdoor experiences. Visitors flock to this destination for its stunning scenery and tranquil atmosphere. The area boasts accessible venues such as resorts and a scenic boardwalk, perfect for leisurely strolls. Notable attractions include the inviting local beaches, a nudist beach for the more adventurous, and the serene bay, making it an ideal spot for relaxation and exploration.
  • Pelican Key: Pelican Key is a vibrant neighbourhood situated around Simpson Bay, known for its breathtaking coastal views and outdoor activities. This area attracts travellers with its stunning beaches and lively atmosphere, making it an excellent choice for beach lovers. The neighbourhood features a variety of resorts and educational venues, as well as a nearby casino for those looking to try their luck. With beautiful beaches and a nudist beach, Pelican Key is a fantastic destination for both relaxation and excitement.
  • Cole Bay: Located just 1.4km from Simpson Bay, Cole Bay is a bustling city that offers a unique blend of beach and outdoor experiences. This vibrant locale is perfect for visitors seeking both relaxation and adventure, with accessible resorts and boardwalks that invite exploration. The area is home to stunning beaches and a nudist beach, ensuring that sun-seekers can find their perfect spot. Cole Bay's welcoming atmosphere and scenic views make it a must-visit destination during your vacation.

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 simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking an extended stay for even greater savings. To discover a Vrbo property that suits 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!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for creating new trips, managing your travel plans, and reviewing your bookings. Your saved or reserved properties are conveniently categorized into Potential, Upcoming, or Current Trips. 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. 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)
  • Flamingo Beach (0.5 mi / 0.8 km)
  • Simpson Bay Beach (1 mi / 1.6 km)
  • Maho Bay (1.6 mi / 2.5 km)
  • Mullet Bay (2 mi / 3.3 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?
Stay in a vacation home in Pelican Key and experience one of Simpson Bay’s most popular areas. Hollywood Casino and Lay Bay Beach are two of the big attractions here that’ll keep you entertained during your visit.
What is the most popular type of vacation rental accommodation in Simpson Bay?
Villas are the most popular style of vacation rental in Simpson Bay, according to our data. Even if you have something bigger or smaller in mind, Vrbo has properties in many sizes and shapes. Compare our options to find your perfect Simpson Bay pad.
How much does it cost to rent a vacation rental in Simpson Bay?
A number of factors influence how much you’ll pay for a vacation rental in Simpson Bay, such as the length of stay, season and type of property. But, all Vrbo homes have something in common — excellent value. Simply enter your travel dates to find your home away from home.
How much does it cost to rent a beach house in Simpson Bay?
When you travel and the style and size of the property will influence how much you’ll pay for your beachside stay. Click on your Simpson Bay travel dates to see your options on Vrbo. Can’t live without a private pool? Use our filters to select the amenities and features you want in your beach house.
Are there pet-friendly vacation rentals in Simpson Bay?
With 216 vacation rentals that welcome pets, your happy hound can join in the fun on your Simpson Bay break. Use the filter tool to browse our pet-friendly vacation rentals and find your pawfect digs on Vrbo.
Can I rent a house with a pool in Simpson Bay?
Grab your swimwear and inflatable unicorn, because there are 155 houses with a private pool in Simpson Bay. Kick back at one of these superb vacation rentals and every day can be a pool day. Simply enter your dates into Vrbo, then check the “pool” filter to find the perfect place for a splashing good time!
What are popular rental amenities in Simpson Bay?
Some of the most popular rental amenities people are searching for in Simpson Bay include nearby museums, a nearby river and a nearby waterfront. Whether you’re on a trip with buddies, family or even pets, Vrbo vacation homes feature the best amenities for hanging out with the people that matter most.
Are there large group vacation rentals in Simpson Bay?
Simpson Bay has 25 vacation properties that can cater to 10 or more people. These stays come with all the space you need to share good times with loved ones.
Are there vacation rentals in Simpson Bay that welcome kids?
With 216 family-friendly vacation properties to select from in Simpson Bay, now is a great time to introduce the kids to the excitement of travel. Simply click on our “Properties good for families” filter box to find stays that feature amenities ideal for families on the move, such as full kitchens, outdoor spaces, entertainment areas and bunk beds.
What are the top attractions for families in Simpson Bay?
Keeping the kids happy during your stay in Simpson Bay is a cinch with these awesome family-friendly attractions:

  • Maho Beach
  • Mullet Bay Beach
  • Grand Case Beach

Are there one-bedroom vacation rentals in Simpson Bay?
Yes, you can take your pick from 66 one-bedroom rentals in Simpson Bay. Whether you’d like a townhouse or an upmarket condo, our one-bedroom rentals are perfect if you don’t need a lot of space. One of the main perks of having your own digs? You’ll never have to share your trip with strangers.
Can I find two-bedroom vacation rentals in Simpson Bay?
Gather your besties and enjoy total privacy and comfort in one of the 74 two-bedroom vacation properties Simpson Bay has to offer.
Are there vacation rentals with WiFi in Simpson Bay?
You’ll have a choice of 85 vacation rentals with WiFi in Simpson Bay. If you’d like to disconnect from the world during your trip, but still want to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Simpson Bay?
Simpson Bay has 208 vacation rentals where you’ll be able to unwind in air-conditioned comfort. To find a stay on Vrbo with this amenity, enter your dates of travel and use the convenient filters to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Simpson Bay?
The minimum age is usually 16, 18 or 21. It can differ between properties on Vrbo, so look at the rules of your chosen Simpson Bay vacation rental before booking your trip.
How long can I rent a vacation rental in Simpson Bay for?
The length of time you can book a vacation rental in Simpson Bay is up to the property. Just enter your chosen travel dates to display a list of options offering extended stays. With tons of creature comforts like washing machines and air conditioning, as well as some offering weekly or monthly discounted prices, you’re sure to get someplace just right to call your home away from home in Simpson Bay.

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