Simpson Bay vacation rentals

We found 3,283 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Find the perfect place for your stay in Simpson Bay by choosing from 66 houses, 80 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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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)
  • Cuisinart Resort Golf Course (9.8 mi / 15.8 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?

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.

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