Simpson Bay vacation rentals

We found 3,241 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Simpson Bay by choosing from 61 houses, 130 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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  • A place for everyone
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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. 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)
  • 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 when booking a vacation rental?
Pelican Key is one of the most desirable neighborhoods where you’ll find a vacation property in Simpson Bay. While here, drop by impressive sights such as Hollywood Casino and Lay Bay Beach.
What is the most popular type of vacation rental accommodation in Simpson Bay?
Condos are the most popular style of vacation rental in Simpson Bay, according to our data. Even if you’ve got something a little different in mind, Vrbo has properties in a variety of shapes and sizes. Take a look at our options to find your perfect match.
How much does it cost to rent a vacation rental in Simpson Bay?
Length of stay, property type and time of year are some of the conditions that can determine the price of a vacation home. Simply enter your dates of travel to find your perfect fit. From comfy cabins to expansive luxury villas, all Vrbo vacation rentals offer amazing value.
How much does it cost to rent a beach house in Simpson Bay?
Prices for beach houses in Simpson Bay can differ depending on the type and size of the property and when you plan to travel. All you need to do is enter your travel dates into Vrbo and the number of guests to view your vacation rental options and prices. From there you can use the filters to refine your search results by ratings, nearby activities and more.
Are there pet-friendly vacation rentals in Simpson Bay?
Yes. There are. You can choose from 222 vacation rentals that cater to pets in Simpson Bay. Some of our pet-friendly vacation rentals come with an outdoor space for your fur baby to play around in, complimentary treats, special dog beds and proximity to parks or green space. Apply the “Pets allowed” filter to find your place on Vrbo.
Can I rent a house with a pool in Simpson Bay?
Mark the “pool” box in our handy filter tool and pick from 154 houses with private pools in Simpson Bay on Vrbo. Morning swim, sunset soak or midnight dip? How you spend your free time is up to you when your Vrbo vacation home boasts its own swimming pool.
What are popular rental amenities in Simpson Bay?
Tennis, ski-in/ski-out facilities and a swimming pool are the most popular rental amenities in Simpson Bay. Whether you plan to go by yourself, with your spouse or a group of friends, Vrbo can help you find a vacation rental that matches your tastes with all the conveniences you’re looking for.
Are there large group vacation rentals in Simpson Bay?
With 22 properties that can host 10 or more guests in Simpson Bay, you don’t have to leave anyone off your guest list. From extended family vacations to special events like weddings and birthday parties, Vrbo can help you find a large group rental to match the occasion.
Are there vacation rentals in Simpson Bay that welcome kids?
With 206 family-friendly vacation rentals available in Simpson Bay, now is a great time to introduce your children to the pleasures of travel. Click on our “Properties good for families” filter box to find stays that feature amenities perfect for families on the move, like multiple bedrooms, swimming pools, hot tubs and bunk beds.
What are the top attractions for families in Simpson Bay?
Keep the kids happy at these popular family-friendly attractions in Simpson Bay:

  • Simpson Bay Beach
  • Flamingo Beach
  • Kim Sha Beach

Are there one-bedroom vacation rentals in Simpson Bay?
You can choose from 75 one-bedroom rentals in Simpson Bay. Whether you’re looking for a comfy cottage or an upmarket condo, our one-bedroom rentals are great if you don’t require a lot of space. One of the perks of having your own place? You’ll never need to share your vacation with strangers.
Can I find two-bedroom vacation rentals in Simpson Bay?
Simpson Bay has 72 two-bedroom properties that you can choose from. Discover a vacation home with all the privacy and space you’re looking for at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Simpson Bay?
Choose from 87 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 214 vacation rentals where you can kick back in air-conditioned comfort. To locate a stay on Vrbo that comes with this amenity, enter your desired travel dates and use the filter tool to select the “air conditioning” box.
How old do you have to be to rent a vacation rental in Simpson Bay?
You’ll have to check with the Simpson Bay vacation rental you’d like on Vrbo as age restrictions differ. However, it’s normally 16, 18 or 21.
How long can I rent a vacation rental in Simpson Bay for?
It’s really down to the Simpson Bay property. To browse available options offering extended stays, just enter your travel dates and number of people into Vrbo’s search page. You can look forward to having the property to yourself, along with home comforts such as a fully-equipped kitchen, air conditioning and an outdoor space to run around in. Keep an eye out for any long-term stays that offer weekly or monthly discounts.
Does Vrbo offer discounts for vacation homes in Simpson Bay?
In Simpson Bay, you’ll find amazing bargains and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re after a mini escape or a longer stay, we have a variety of options to match your style.

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