Simpson Bay holiday homes

We found 3,248 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Simpson Bay by choosing from 46 houses, 174 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:30 Oct - 6 Nov

Image gallery for LUXURY 4 BEDROOM VILLA - JARDIN CREOLE TERRES BASSE - JUST TWO MINUTES TO BEACH

Pool
10 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)

LUXURY 4 BEDROOM VILLA - JARDIN CREOLE TERRES BASSE - JUST TWO MINUTES TO BEACH

Les Terres Basses

8% off
Price is NZ$16,512
for 7 nights, 1 villa
NZ$2,359 per night
includes taxes & fees
LUXURY 4 BEDROOM VILLA - JARDIN CREOLE TERRES BASSE - JUST TWO MINUTES TO BEACH

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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:

  • 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)
  • 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 home?
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 home accommodation in Simpson Bay?
Villas are the most popular style of holiday home in Simpson Bay, according to our data. Even if you have something bigger or smaller in mind, Bookabach 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 home in Simpson Bay?
A number of factors influence how much you'll pay for a holiday home in Simpson Bay, such as the length of stay, season and type of property. But, all Bookabach 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 Bookabach. 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 homes in Simpson Bay?
With 216 holiday homes 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 homes and find your pawfect digs on Bookabach.
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 homes and every day can be a pool day. Simply enter your dates into Bookabach, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular home amenities in Simpson Bay?
Some of the most popular home 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, Bookabach holiday homes feature the best amenities for hanging out with the people that matter most.
Are there large group holiday homes 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 homes 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 homes in Simpson Bay?
Yes, you can take your pick from 66 one-bedroom homes in Simpson Bay. Whether you'd like a townhouse or an upmarket condo, our one-bedroom homes 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 homes 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 homes with WiFi in Simpson Bay?
You'll have a choice of 85 holiday homes 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 Bookabach.
How can I find holiday homes with air conditioning in Simpson Bay?
Simpson Bay has 208 holiday homes where you'll be able to unwind in air-conditioned comfort. To find a stay on Bookabach 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 home in Simpson Bay?
The minimum age is usually 16, 18 or 21. It can differ between properties on Bookabach, so look at the rules of your chosen Simpson Bay holiday home before booking your trip.
How long can I rent a holiday home in Simpson Bay for?
The length of time you can book a holiday home 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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