Simpson Bay holiday lettings

We found 3,281 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Simpson Bay by choosing from 68 houses, 135 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.

Holiday rentals with weekly discounts - Simpson Bay

Showing deals for:3 Oct - 10 Oct
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Why visit Simpson Bay

  • Stunning Beaches: Relax on the picturesque Simpson Bay Beach, renowned for its breathtaking views and tranquil atmosphere.
  • Outdoor Adventures: Engage in a variety of eco-friendly activities that immerse you in the natural beauty of the area.
  • Vibrant Local Culture: Explore nearby beaches and experience the lively local culture, ensuring a memorable stay.
  • Diverse Accommodation: Choose from an array of delightful holiday rentals, from charming condos to luxurious villas.
  • Family-Friendly Atmosphere: Perfect for both family holidays and romantic getaways, Simpson Bay caters to all travellers.

Popular types of accommodation in Simpson Bay

Planning a getaway to Simpson Bay? The excitement begins with selecting your perfect accommodation. From charming condos to luxurious villas and cosy apartments, there’s a variety of options to suit every traveller. Explore our fantastic selection of Simpson Bay holiday rentals and vacation rentals, ensuring you find the ideal home away from home. Enjoy transparency and savings as you discover the best Simpson Bay resort for your stay.

  • Condos: The top choice for holidaymakers in Simpson Bay, offering modern amenities and stunning views.
  • Villas: A luxurious option for those seeking spacious accommodations with private pools and gardens.
  • Apartments: A practical choice for couples or small families, providing comfort and convenience in a central location.
  • Houses: Ideal for larger groups, these homes offer a homely feel with plenty of space.
  • Guest Houses: A charming and affordable alternative, perfect for meeting fellow travellers.**

Top attractions in and around Simpson Bay

Simpson Bay, Sint Maarten, is perfect for beach and outdoor enthusiasts seeking scenic beauty. Visitors can enjoy stunning beaches and parks, with Simpson Beach being a must-visit spot. This destination offers an eco-friendly experience, making it ideal for travellers wanting to immerse themselves in nature. Whether you're planning a family holiday or a romantic getaway, Simpson Bay promises a delightful escape filled with sun, sand, and adventure.

  • Simpson Bay Beach: A stunning stretch of golden sand with a vibrant beach vibe, perfect for sunbathing and water sports. The tranquil waters are ideal for swimming and enjoying picturesque sunsets.
  • Seaside Nature Park: Located 621m from Simpson Bay, this eco-friendly park offers lush landscapes and outdoor activities. It's a family-friendly destination where you can explore nature trails and engage in birdwatching.
  • Kim Sha Beach: Another beautiful beach within Simpson Bay, Kim Sha Beach boasts a lively atmosphere, with beach bars and restaurants nearby, making it a great spot for relaxation and socialising.

Things to do recommended for couples

For a romantic outing in Simpson Bay, take a scenic stroll along Philipsburg Boardwalk, just 1.9km away. Enjoy the beach vibes, savour a meal at a seaside restaurant, and watch the sunset together, creating unforgettable memories.

Things to do recommended for families

Families visiting Simpson Bay can experience the thrill of Rainforest Adventures St. Maarten, a recreation park located 1.2km from the bay. This park offers wellness and relaxation vibes, making it a perfect day out for both kids and adults.

Things to do recommended for groups

Groups visiting Simpson Bay can enjoy a round of golf at Mullet Bay Golf, located 1.2km from the area. The course offers a fantastic outdoor atmosphere, perfect for sports enthusiasts looking to bond and enjoy the beautiful surroundings together.

Booking with Vrbo is simple

Are you hoping to save on your upcoming getaway? It might be worth considering some flexibility with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To help you discover the perfect Vrbo property that fits your budget, feel free to utilise our filters to sort by price, location, and type of holiday rental.

Where to stay in and around Simpson Bay

Simpson Bay offers a delightful blend of beachside relaxation and scenic outdoor adventures. Visitors can unwind on the stunning Simpson Bay Beach, known for its breathtaking views and romantic atmosphere. The area boasts a range of perfect holiday rentals, making it ideal for families and couples alike. Explore nearby beaches and enjoy the vibrant local culture, ensuring a memorable vacation experience filled with excursions and picturesque scenery.

  • Cole Bay: Cole Bay is a vibrant city located a mere 559m from Simpson Bay, making it an easy and appealing destination for visitors. This area is renowned for its stunning beaches and outdoor activities, offering picturesque scenery that attracts sun-seekers and nature enthusiasts alike. In Cole Bay, you can explore the local boardwalk, unwind at charming resorts, and enjoy the nearby nudist beach. Attractions such as the tranquil bay and sandy shores provide a perfect backdrop for relaxation and exploration. The community vibe combined with natural beauty makes Cole Bay a delightful spot to visit.
  • Beacon Hill: Nestled within the vicinity of Simpson Bay, Beacon Hill is a quaint village that invites travellers to bask in its beachside charm. Known for its outdoor experiences and scenic views, Beacon Hill offers a serene escape for those looking to unwind. Visitors can enjoy local resorts and venture along the boardwalk, taking in the coastal atmosphere. The proximity to beautiful beaches and the nudist beach adds to the allure, making it an ideal location for sunbathing and swimming. Beacon Hill’s relaxed ambiance and natural beauty create an inviting atmosphere for all who visit.
  • Pelican Key: Pelican Key is a picturesque neighbourhood that lies around Simpson Bay, attracting tourists with its stunning coastal views and outdoor activities. This area is perfect for those seeking a blend of relaxation and adventure, featuring lovely resorts and access to scenic boardwalks. With its beautiful beaches and the nearby nudist beach, Pelican Key offers ample opportunities for sun-soaked fun and exploration. The neighbourhood’s friendly atmosphere and breathtaking scenery make it a must-visit destination for anyone looking to enjoy the beauty of Sint Maarten.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

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

When travelling with a group, family, pets, or seeking longer stays, it's important to apply the right filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Simpson Bay with a group: Think about how many bedrooms you'll require, as well as features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search to include all of these options and more on Vrbo.
  • Traveling to Simpson Bay with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Simpson Bay: For many families, a holiday wouldn’t feel complete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most 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 holiday rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides you with a convenient platform to plan new holidays, manage your existing arrangements, or review your bookings. Your saved or reserved properties are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/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-see attractions in the area. 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:

  • 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 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)
  • 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 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?
Stay in a holiday 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 holiday rental accommodation in Simpson Bay?
Villas are the most popular style of holiday 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 holiday rental in Simpson Bay?
A number of factors influence how much you'll pay for a holiday 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 holiday rentals in Simpson Bay?
With 216 holiday 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 holiday 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 holiday 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 holiday homes feature the best amenities for hanging out with the people that matter most.
Are there large group holiday rentals in Simpson Bay?
Simpson Bay has 25 holiday 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 holiday rentals in Simpson Bay that welcome kids?
With 216 family-friendly holiday 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 holiday 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 holiday rentals in Simpson Bay?
Gather your besties and enjoy total privacy and comfort in one of the 74 two-bedroom holiday properties Simpson Bay has to offer.
Are there holiday rentals with WiFi in Simpson Bay?
You'll have a choice of 85 holiday 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 holiday rentals with air conditioning in Simpson Bay?
Simpson Bay has 208 holiday 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 holiday 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 holiday rental before booking your trip.
How long can I rent a holiday rental in Simpson Bay for?
The length of time you can book a holiday 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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