Simpson Bay holiday lettings

We found 3,265 holiday rentals — enter your dates for availability

Find the perfect place for you stay in Simpson Bay by choosing from 81 houses, 140 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:14 Nov - 21 Nov

Image gallery for Luxury 5 Bedroom Villa

Pool Deck
10 out of 10 rating
Exceptional
(5 reviews)

Luxury 5 Bedroom Villa

Les Terres Basses, Collectivité de Saint-Martin

9% off
Price is £6,813
£973 per night
includes taxes & fees
Luxury 5 Bedroom Villa

Find spaces that suit your style

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Find out more about Simpson Bay

Find out more about Simpson Bay

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.

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.

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

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.

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. 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:

  • Aurora International Golf Club (9.9 mi / 16 km)
  • Mullet Bay Golf (1.6 mi / 2.6 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:

  • 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)
  • Maho Beach (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?
When considering a holiday rental in Simpson Bay, Sint Maarten, the area around the Simpson Bay Lagoon is an excellent choice. This vibrant neighbourhood is known for its stunning waterfront views and a lively atmosphere, making it a popular spot for visitors. Staying here, you'll find a variety of rental properties ranging from luxury villas to charming apartments, providing ample options to suit different preferences and budgets.

One of the top attractions in this area is the Simpson Bay Beach, which offers a beautiful stretch of sand superb for sunbathing and water sports. Additionally, the nearby Maho Beach is renowned for its thrilling experience of watching planes land just overhead, creating a unique and memorable spectacle. The proximity to these beaches allows for easy access to a range of activities, including snorkelling and diving excursions.
How much does it cost to rent a holiday home in Simpson Bay?
Prices for holiday rentals in Simpson Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Simpson Bay to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Simpson Bay holiday house rentals?
You can find great discounts on house rentals in Simpson Bay on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Simpson Bay?
For renting a beach house in Simpson Bay, Sint Maarten, the coastline along Simpson Bay Beach is an excellent choice. This area features a variety of holiday rentals, many of which are directly on the beach and offer stunning views of the Caribbean Sea. Properties here often come equipped with amenities such as private balconies, outdoor seating areas, and access to swimming pools, making them ideal for families or couples seeking a relaxing getaway.

Nearby, the vibrant nightlife and dining options in the Simpson Bay area add to the appeal. Travellers can find beach houses that offer easy access to local restaurants and bars, with some properties even featuring outdoor grills and kitchens for alfresco dining.
What is the most popular type of holiday rental accomodation in Simpson Bay?
In Simpson Bay, apartments are the most popular type of holiday rental, with around 129 available throughout the area. Many of these apartments are situated in lively neighbourhoods close to the beach, offering easy access to local restaurants and shops. Most rooms come equipped with modern amenities such as fully equipped kitchens, comfortable living areas, and private balconies or patios that provide stunning views of the Caribbean Sea.
Are there any family house rentals in Simpson Bay?
In Simpson Bay, Sint Maarten, there are numerous family-friendly holiday rentals available, with around 165 properties suiting various needs. This vibrant area offers a mix of spacious homes, often featuring multiple bedrooms, large living areas, and kitchens equipped for preparing family meals. Many residences also include outdoor spaces such as patios or gardens, superb for children to play and families to gather.
Can I rent a holiday home with a pool or hot tub in Simpson Bay?
In Simpson Bay, Sint Maarten, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 268 options to choose from. This vibrant area is known for its stunning beaches and lively atmosphere, making it an excellent destination for travellers seeking relaxation and entertainment.
Can I find long-stay holiday rentals in Simpson Bay?
A long-stay holiday rental in Simpson Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Simpson Bay?
In Simpson Bay, there are numerous pet-friendly house rentals available, providing a fantastic opportunity for travellers looking to enjoy the beautiful Caribbean environment with their furry companions. Many of these holiday homes come equipped with amenities such as private pools, spacious outdoor terraces, and fully equipped kitchens, ensuring a comfortable and convenient stay.
Are there any remote work holiday rentals in Simpson Bay?
In Simpson Bay, Sint Maarten, there are numerous options for remote work holiday rentals, with around 301 available to choose from. This vibrant area is known for its stunning beaches and lively atmosphere, making it an ideal place for both work and leisure. Many properties come equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated office spaces, ergonomic desks and chairs, and laptop workstations. Some rentals may even feature additional comforts such as safes for personal belongings and computer monitors for enhanced productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Simpson Bay holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Simpson Bay with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Simpson Bay?
In Simpson Bay, popular rental amenities include pools, kitchens equipped with essential items such as refrigerators, cookware, dishware, and utensils, as well as coffee makers for a convenient start to the day. Many properties provide a refreshing pool area, superb for relaxation after enjoying the nearby beaches and vibrant nightlife.
When is the best time to visit Simpson Bay for a holiday rental?
September is the most popular month to visit Simpson Bay, as it marks the tail end of the peak season, which runs from July to September. This period is ideal for those seeking a vibrant atmosphere combined with the chance to enjoy beautiful beaches and a variety of water sports. With warm temperatures averaging around 28°C, you can comfortably indulge in outdoor activities like snorkelling, sailing, and exploring the stunning coastline.

As summer transitions into autumn, September offers a delightful mix of lively beach parties and quieter sightseeing opportunities. You'll find that many local events and festivals take place during this time, allowing you to experience the rich culture of Sint Maarten while mingling with fellow travellers.

If you're looking for a more budget-friendly option, consider planning your visit in October. This month marks the beginning of the low season, where you can still enjoy lovely weather and fewer crowds. It's a great time to explore the local markets and enjoy a more relaxed pace while soaking in the island's charm.
How early should I book a Simpson Bay holiday rental?
Book your Simpson Bay holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Simpson Bay?
In Simpson Bay, Sint Maarten, visitors can enjoy a blend of natural beauty and vibrant nightlife. The stunning Simpson Bay Beach is a major attraction, offering soft sands and crystal-clear waters, great for sunbathing and water sports. Nearby, the Simpson Bay Lagoon provides opportunities for boat tours and yachting, showcasing the picturesque scenery of the area.

The lively nightlife scene can be found along the waterfront, where numerous bars and restaurants serve both local and international cuisine, making it an ideal spot for dining and entertainment. Additionally, the proximity to attractions like the Maho Beach, famous for its close-up views of arriving aircraft, adds to the area's appeal.
Can I change or cancel my Simpson Bay home rental booking on Vrbo?
To find Simpson Bay holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Simpson Bay holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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