Simpson Bay holiday homes

We found 3,239 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Simpson Bay by choosing from 42 houses, 171 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:11 Dec - 18 Dec

Dining
Pool
Interior
Property grounds
Exceptional
(11 reviews)

Villa Oasis

Orient Bay

8% off
NZ$13,290
for 7 nights, 1 villa
NZ$1,899 per night
includes taxes & fees
Villa Oasis
Private kitchen
Pool
Living area
Room
Exceptional
(17 reviews)

Luxurious Villa " Sea La Vie" in Pelican Key

Simpson Bay

5% off
NZ$8,115
for 7 nights, 1 villa
NZ$1,159 per night
includes taxes & fees
Luxurious Villa " Sea La Vie" in Pelican Key
Pool
Outdoor dining
Beach
Exterior
Exceptional
(21 reviews)

💖💖💖studio nature reserve pool/beach/kayak included

Cul de Sac

8% off
NZ$2,920
for 7 nights, 1 apartment
NZ$417 per night
includes taxes & fees
💖💖💖studio nature reserve pool/beach/kayak included
Exterior
Outdoor dining
Beach
Private kitchen
Exceptional
(21 reviews)

❤️❤️❤️studio beyondsea grand case beach ⭐️⭐️⭐️⭐️

Grand Case

8% off
NZ$2,654
for 7 nights, 1 apartment
NZ$379 per night
includes taxes & fees
❤️❤️❤️studio beyondsea grand case beach ⭐️⭐️⭐️⭐️
Private kitchen
Living area
Room
Interior
Exceptional
(5 reviews)

Escape to Tranquility 2-bedroom modern home at waterfront with fast Internet.

Philipsburg

13% off
NZ$3,045
for 7 nights, 1 apartment
NZ$435 per night
includes taxes & fees
Escape to Tranquility 2-bedroom modern home at waterfront with fast Internet.
Private kitchen
Property grounds
Living area
Room
Exceptional
(18 reviews)

2 BR 2 BA, beachfront condo, amazing oceanview, private beach access

Simpson Bay

8% off
NZ$4,297
for 7 nights, 1 apartment
NZ$614 per night
includes taxes & fees
2 BR 2 BA, beachfront condo, amazing oceanview, private beach access

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Why visit Simpson Bay

  • Pristine beaches: Enjoy Simpson Bay Beach with its soft sands and crystal-clear waters ideal for family outings and water sports.
  • Lush outdoor spaces: Explore nearby parks perfect for leisurely strolls and eco-friendly adventures.
  • Vibrant local culture: Experience a lively atmosphere with diverse dining options and local charm.
  • Relaxation and recreation: Combine sun-soaked relaxation with exciting outdoor activities in a scenic setting.
  • Memorable coastal experience: Immerse yourself in the unique blend of natural beauty and dynamic local vibes.

Top attractions in and around Simpson Bay

Simpson Bay, Sint Maarten offers a delightful blend of beach and outdoor experiences perfect for eco-friendly travellers. Enjoy the pristine sandy shores and lush parks that provide a scenic backdrop for relaxation and exploration. This vibrant city is an ideal destination for those seeking a mix of natural beauty and outdoor activities, making it a must-visit on your holiday itinerary.

  • Simpson Bay Beach: A stunning stretch of golden sand perfect for soaking up the sun and enjoying the vibrant beach vibes. The calm waters are great for swimming and water sports, making it a popular spot for both relaxation and adventure.
  • Seaside Nature Park: An eco-friendly haven offering a family-friendly environment. Enjoy outdoor activities like hiking and birdwatching while immersing yourself in the natural beauty of the park.
  • Kim Sha Beach: Another beautiful beach in Simpson Bay, known for its lively atmosphere. Ideal for families and friends, it's a great place to unwind, swim, and indulge in beachfront dining.

Things to do recommended for couples

For a romantic getaway in Simpson Bay, indulge in a sunset dinner at a beachfront restaurant, take a leisurely stroll along the pristine beach, or enjoy a couple's massage at a local spa. Don't forget to explore the vibrant nightlife for an unforgettable evening together.

Things to do recommended for families

In Simpson Bay, families can enjoy a day at the beautiful Mullet Bay Beach, perfect for swimming and building sandcastles. The kids will love exploring the butterfly farm and taking a fun-filled boat trip around the island, making unforgettable memories together.

Things to do recommended for groups

Groups visiting Simpson Bay can unwind on the beautiful Maho Beach, where planes land overhead. They can also enjoy a boat trip to explore the nearby islands and dive into vibrant local culture with a visit to the lively markets and beachside bars.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

Whether you're journeying with a group, travelling as a family, bringing your pets, or seeking extended stays, be sure to apply the appropriate filters. Here are some Vrbo booking suggestions 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 an outdoor area for group gatherings. Luckily, you can easily apply filters for all of these options, and plenty more, on Vrbo.
  • Traveling to Simpson Bay with young kids: Traveling with little ones can be a challenge. You have to make sure they’re comfortable and safe, with access to facilities suited to their age, like a private swimming pool. It’s also wise to think about how close you are to attractions that are great for families.
  • Taking your pets with you to Simpson Bay: For many, a family getaway wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that every member of the family feels at home.
  • Planning for a long term stay visiting Simpson Bay: If you're after holiday rentals offering deals for month-long stays or more, you've come to the right place. With the proper filter, you can easily find and save on monthly rentals. You might also consider including extras like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Simpson Bay

Simpson Bay, Sint Maarten, offers a delightful blend of stunning beaches and vibrant local culture. Visitors can soak up the sun at Simpson Bay Beach, renowned for its soft sands and crystal-clear waters. The area is perfect for romantic strolls, family-friendly outings, and exciting water sports. With a lively atmosphere and numerous dining options, Simpson Bay is a fantastic base to explore the beautiful surroundings while enjoying a truly memorable holiday experience.

  • Cole Bay: Situated a mere 1km from Simpson Bay, Cole Bay is a vibrant city that beckons visitors with its stunning beaches and breathtaking scenery. The area is perfect for outdoor enthusiasts, offering a variety of activities such as leisurely strolls along the boardwalk or educational visits to modern colleges. The local bay is a prominent feature, and its inviting beaches make it a prime spot for sunbathing and swimming. With a blend of scenic beauty and educational opportunities, Cole Bay is an ideal stop on your holiday.
  • Pelican Key: Nestled close to Simpson Bay, Pelican Key is a charming neighbourhood known for its picturesque beaches and outdoor experiences. Travellers flock here to enjoy the serene beauty of the bay and partake in activities like hiking along scenic trails. The area's resorts offer relaxation and leisure, making it a perfect escape for those looking to unwind. Pelican Key truly captures the essence of island life, providing a tranquil setting filled with natural beauty and recreational opportunities.
  • Beacon Hill: This quaint village, located in proximity to Simpson Bay, offers a delightful mix of scenic attractions and outdoor activities. Visitors are drawn to its beautiful beaches and stunning water features, making it a picturesque spot for relaxation and exploration. The village is also home to educational facilities and a lovely boardwalk that invites leisurely strolls. Beacon Hill's combination of natural beauty and community charm makes it an enchanting destination for tourists seeking to immerse themselves in the local culture.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January78.3°F (25.7°C)No Rain (Dry)Mostly Sunny
February77.7°F (25.4°C)No Rain (Dry)Mostly Sunny
March77.5°F (25.3°C)No Rain (Dry)Mostly Sunny
April78.4°F (25.8°C)No Rain (Dry)Mostly Sunny
May80.1°F (26.7°C)Light RainMostly Sunny
June81.5°F (27.5°C)Light RainMostly Sunny
July82.0°F (27.8°C)Light RainMostly Sunny
August82.6°F (28.1°C)Light RainMostly Sunny
September82.9°F (28.3°C)Light RainMostly Sunny
October82.6°F (28.1°C)Light RainMostly Cloudy
November81.3°F (27.4°C)Light RainMostly Cloudy
December79.7°F (26.5°C)No Rain (Dry)Mostly Sunny

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to organise by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a dedicated space to start new adventures, continue your current plans, or review and organise your bookings. Your saved or reserved properties are neatly categorised into Potential, Upcoming, or Current Trips. To discover the Trip Boards, please visit: https://www.bookabach.co.nz/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:

  • Maho Beach (1.6 mi / 2.5 km)
  • Kim Sha Beach (0.3 mi / 0.5 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?
When considering a holiday rental in Simpson Bay, Sint Maarten, the Simpson Bay area itself is an excellent choice for a delightful stay. This vibrant neighbourhood is known for its stunning beachfront, making it an ideal spot for sun-seekers and water sports enthusiasts alike. With a variety of properties available, from charming villas to modern apartments, visitors can find something to suit their preferences.One of the top attractions in the area is the beautiful Simpson Bay Beach, where you can relax on the soft sands or partake in various water activities such as snorkelling and jet skiing. Additionally, the lively option of the Simpson Bay Marina offers a range of dining options and boutique shops, providing a superb blend of relaxation and entertainment.For those looking to explore further, the nearby Maho Beach is famous for its proximity to the airport, where you can witness planes landing just above your head—an experience that is both thrilling and unforgettable.
Where are the best areas for renting a beach house in Simpson Bay?
For renting a beach house in Simpson Bay, the area along the beachfront offers stunning views and easy access to the sandy shores. The stretch near the Simpson Bay Lagoon is particularly popular, where travellers can find a variety of beachfront properties, including modern villas and charming bungalows. Many of these rentals come equipped with amenities such as private pools, outdoor patios for al fresco dining, and fully equipped kitchens, making them ideal for families or groups looking to enjoy a relaxing beach holiday.Additionally, properties in the vicinity of the Simpson Bay Beach offer convenient access to local shops, restaurants, and vibrant nightlife, adding to the appeal for those seeking both relaxation and entertainment. Many accommodations also feature water sports facilities, allowing guests to partake in activities like kayaking and paddleboarding right from their doorstep.Nearby, the Maho Beach area is known for its lively option and proximity to the famous airplane landing views. Beach houses here often include outdoor lounges and easy beach access, great for enjoying the sun and sea.
What is the most popular type of holiday rental accomodation in Simpson Bay?
In Simpson Bay, the most popular type of holiday rental accommodation is apartments, with around 684 available in the area. These apartments are typically situated in lively neighbourhoods close to the beach and local amenities, offering guests the convenience of fully equipped kitchens, comfortable living spaces, and often stunning views of the Caribbean Sea. Many of these units also include balconies or terraces, great for enjoying the tropical surroundings.Condos are another prevalent choice, with approximately 392 options available. These condos frequently provide resort-style amenities such as pools, fitness centres, and easy access to the beach, making them ideal for travellers seeking a more luxurious experience.For those looking for more spacious rooms, there are about 244 villas available, which come with private gardens, outdoor seating areas, and multiple bedrooms. These villas are great for families or groups wanting to have a more secluded stay while still being close to the vibrant setting of Simpson Bay. Lastly, there are around 108 holiday houses that offer a homely feel with ample living space and the convenience of self-catering facilities.
Are there any family house rentals in Simpson Bay?
In Simpson Bay, Sint Maarten, there is a wealth of family-friendly house rentals available, with around 143 options to choose from. This vibrant locale is well-known for its stunning beaches and lively option, making it an ideal destination for families. Many properties boast spacious living areas, fully equipped kitchens, and outdoor spaces where children can play, ensuring comfort and convenience for all guests.Visitors can enjoy easy access to nearby attractions such as the beautiful Maho Beach, famous for its unique proximity to the airport, and the lively Simpson Bay Beach, great for sunbathing and water sports. Additionally, the area is dotted with restaurants and shops, offering a taste of local culture and cuisine.
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 come with pools and hot tubs, with around 262 options to choose from. This beautiful area is renowned for its stunning beaches and vibrant setting, making it a popular destination for travellers seeking relaxation and fun in the sun.Many of the rentals in Simpson Bay offer amenities such as private swimming pools, inviting hot tubs, spacious outdoor terraces, and fully equipped kitchens, ideal for families or groups looking to enjoy a luxurious getaway. Some properties may also feature additional conveniences like barbecue areas, lush gardens, and easy access to the nearby beach, enhancing the overall holiday experience.
Are there pet-friendly house rentals in Simpson Bay?
In Simpson Bay, there is a variety of pet-friendly house rentals available, with over 60 options to choose from. This area is known for its stunning beaches and vibrant setting, making it an ideal destination for travellers looking to bring their furry companions along. Many of the holiday rentals in Simpson Bay come equipped with amenities such as private pools, outdoor terraces, and fully equipped kitchens, suiting the needs of families or groups seeking comfort and convenience during their stay.Simpson Bay itself is close to several pet-friendly points of interest, including beautiful stretches of beach where pets can enjoy the sun and surf. The nearby Mullet Bay Beach is also a popular spot for pet owners, offering expansive sandy areas and calm waters. Additionally, the local eateries and cafes often have outdoor seating options that welcome pets, allowing for a pleasant dining experience with your four-legged friends.
Are there any remote work holiday rentals in Simpson Bay?
In Simpson Bay, Sint Maarten, there is an abundance of remote work-friendly holiday rentals, with around 940 options available. This picturesque area is known for its stunning beaches and vibrant nightlife, making it an ideal destination for those looking to blend leisure with productivity. Many properties come equipped with high-speed Wi-Fi, ensuring seamless connectivity for work-related tasks.Travellers can expect to find a range of amenities designed to enhance their remote working experience, including dedicated workspaces, comfortable seating, and some even offer additional services like limo or town car transportation for easy commutes. The proximity to local cafes and restaurants also provides convenient spots for meetings or a change of scenery. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Simpson Bay?
In Simpson Bay, popular rental amenities include well-equipped kitchens, which allow guests to prepare their own meals, alongside onsite parking for convenience. Many properties also feature coffee and tea makers, ideal for morning brews before heading out to explore the nearby beaches. Balconies and patios are common, providing lovely outdoor spaces to relax and enjoy the tropical surroundings.
When is the best time to visit Simpson Bay for a holiday rental?
The best time to visit Simpson Bay for a holiday rental is during the peak season from July to September. This period is particularly popular among travellers seeking a vibrant setting with plenty of activities. The warm Caribbean climate, with temperatures typically ranging from 25 to 30 degrees Celsius, makes it an ideal time for beach outings, water sports, and exploring the stunning coastline.September is a noteworthy month for visitors, as you can enjoy the tail end of the peak season with slightly fewer crowds compared to July and August. The festive ambience continues, and you can partake in local events while soaking up the sun on beautiful beaches or indulging in the delightful culinary scene.For those looking for a more budget-friendly option, consider visiting in October, when the prices for holiday rentals tend to drop. This transitional period offers a chance to experience the tranquility of Simpson Bay, as fewer tourists mean that you can enjoy your surroundings more peacefully. You can still enjoy pleasant weather and have the opportunity to explore the island's exquisite nature without the busyness of peak season.
What are the top attractions in Simpson Bay?
In Simpson Bay, visitors can enjoy a variety of attractions that highlight the area's vibrant culture and stunning natural beauty. The picturesque Simpson Bay Beach is a major draw, offering soft sands and clear waters, superb for sunbathing or swimming. Close to the beach, you'll find lively beach bars and restaurants where you can sample local cuisine and refreshing cocktails.The Marina at Simpson Bay is another key attraction, where travellers can admire luxury yachts and enjoy waterfront dining. For those interested in nightlife, the area boasts a range of bars and clubs that cater to different tastes, ensuring a lively option after sunset.Nearby, the Maho Beach area is famous for its dramatic plane landings, providing a great experience for aviation enthusiasts and beachgoers alike. Additionally, the nearby Simpson Bay Lagoon offers opportunities for water sports, including kayaking and paddleboarding, making it a great spot for adventure seekers.For a taste of local culture, the nearby island's capital, Philipsburg, is easily accessible and features historical sites, shopping areas, and the vibrant Front Street.
Are all fees included in the Simpson Bay holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Simpson Bay holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Simpson Bay holiday homes?
You can find great discounts on holiday homes in Simpson Bay on Bookabach, 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.
Can I change or cancel my Simpson Bay holiday home booking on Bookabach?
To find Simpson Bay holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Simpson Bay?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Simpson Bay holiday home?
Book your Simpson Bay holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Simpson Bay?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Simpson Bay to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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