Middle Region vacation rentals

We found 46 vacation rentals — enter your dates for availability

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August 2025

September 2025

Scroll through and select from vacation rentals in Middle Region to find one that's perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the amenities you expect for your stay, which might include parking and a pool. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

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Condo/Apartment

Find the best place to stay - Middle Region

Luna Sul Mare - 2 Bed 2.5 Bath Condo with gorgeous ocean view!

Sleeps 4 · 2 bedrooms · 2+ bathrooms

Bell'Mare, 2 Bedroom oceanfront villa and private pool - By Island Properties

Sleeps 4 · 2 bedrooms

Top rated rentals - Middle Region

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Find out more about Middle Region

Why visit Middle Region

Beautiful Beaches: Enjoy breathtaking beaches perfect for relaxation and water activities.
Cultural Experiences: Immerse yourself in the vibrant local culture and friendly community.
Outdoor Adventures: Discover scenic landscapes ideal for exploration and outdoor excursions.
Historic Sites: Visit notable civic buildings that reflect the rich history of Sint Maarten.
Variety of Accommodations: Choose from diverse vacation rentals, including condos and villas, for a comfortable stay.

Popular types of accommodation around Middle Region

Planning your getaway to the Middle Region? You're in for a treat! Discover a range of popular vacation rentals, including condos, villas, and apartments, tailored for every traveller. Explore stunning Sint Maarten properties and enjoy the comfort of villa accommodations in Simpson Bay. With transparent information and great savings, your ideal tourist accommodation is just a click away!

Condos: The top choice for vacation rentals in Middle Region, offering modern amenities and proximity to local attractions.
Villas: A popular option, these spacious homes provide luxury and privacy, perfect for families or groups.
Apartments: Convenient and often centrally located, apartments cater well to solo travellers or couples.
Houses: Ideal for those seeking a home-like atmosphere, these rentals offer comfort and flexibility.
Cottages: Charming and cozy, cottages provide a quaint escape for those looking to unwind in nature.**

Top attractions around Middle Region

Middle Region in Sint Maarten is perfect for a beach and outdoor vacation, offering stunning scenery and cultural experiences. Explore beautiful beaches, visit modern colleges, and discover historic civic buildings. This area is ideal for travellers seeking a blend of relaxation and exploration. Don't miss the chance to enjoy local excursions and delve deeper into what Sint Maarten has to offer. Make your trip memorable by immersing yourself in the vibrant culture and breathtaking landscapes.

Dawn Beach: A stunning beach known for its tranquil atmosphere and soft, powdery sands, perfect for relaxation and sunbathing. The turquoise waters invite swimming and snorkeling, offering a serene escape from the hustle and bustle.
University of St. Martin: A vibrant modern college that fosters a dynamic learning environment. It's a hub of cultural exchange, providing unique insights into local and international perspectives, set against a backdrop of urban sophistication.
Guana Bay: A picturesque bay featuring beautiful scenery and outdoor activities. Ideal for beach lovers, it offers opportunities for swimming, hiking, and enjoying stunning sunsets, making it a perfect spot for nature enthusiasts.

Things to do recommended for couples

For a romantic getaway in Sint Maarten, explore the charming Philipsburg Boardwalk, only 3.2km from Middle Region. Stroll hand in hand along the waterfront, soaking in the beach vibes and enjoying the local atmosphere. It's the perfect spot to create lasting memories together.

Things to do recommended for families

While in Middle Region, families can experience the excitement of Rainforest Adventures St. Maarten, located 3.2km away. This recreation park offers wellness vibes and relaxation, making it a perfect spot for a fun-filled day with the kids.

Things to do recommended for groups

In Middle Region, Sint Maarten, your group can enjoy a thrilling night at Hollywood Casino or Paradise Plaza, both offering a vibrant casino atmosphere. For a more active experience, head to Mullet Bay Golf for some outdoor sports fun amidst beautiful scenery.

What do I need to keep in mind when booking a vacation around Middle Region

If you’re travelling with a group, family, pets, or planning an extended stay, it’s important to prioritize your preferences when filtering your options. Here are some helpful booking tips for using Vrbo.

Traveling to Middle Region with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
Traveling to Middle Region with young kids: Traveling with young children can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for families.
Taking your pets with you to Middle Region: For many, a family getaway isn’t truly satisfying without their furry companion along for the adventure. If this resonates with you, we invite you to explore Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone, including your four-legged friend, feels comfortable and at home.
Planning for a long term stay visiting Middle Region: If you’re in search of vacation rentals that offer great deals for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay around Middle Region

Middle Region in Sint Maarten offers a delightful blend of beachside beauty and scenic outdoor adventures. This charming neighbourhood is perfect for those seeking relaxation and romance, with friendly locals eager to share their vibrant culture. Nearby attractions invite you to explore the essence of Saint Martin, making it an ideal base for excursions. Whether you’re unwinding by the shore or discovering hidden gems, Middle Region promises an unforgettable vacation experience.

Philipsburg: Philipsburg, the capital city of Sint Maarten, is a vibrant coastal destination located a mere mile from Middle Region. This bustling city is renowned for its stunning beaches and lively boardwalk, making it a perfect spot for sun-seekers and outdoor enthusiasts. Visitors can indulge in various activities ranging from shopping at local boutiques to exploring educational exhibits. The picturesque waterfront offers breathtaking views of the bay, while the nearby nudist beach provides a unique experience for those seeking it. Philipsburg is also home to a variety of resorts that cater to travellers looking for relaxation and entertainment.
Oyster Pond: Just 1.6km away from Middle Region, Oyster Pond is a serene coastal city that enchants visitors with its beautiful scenery and tranquil beaches. Known for its luxurious resorts and waterfront activities, this area is perfect for those looking to unwind in a picturesque setting. The local boardwalk is an excellent spot for leisurely strolls, while educational opportunities abound for those interested in the island’s rich history. With easy access to both the beach and nudist beach, Oyster Pond offers a unique blend of relaxation and adventure in a stunning natural environment.
Sucker Garden: Located only half a mile from Middle Region, Sucker Garden is a charming neighbourhood that offers visitors a taste of local life and leisure. Known for its nearby beaches and outdoor activities, Sucker Garden is perfect for those looking for a laid-back experience. The area is home to various attractions, including a casino for entertainment seekers and beautiful boardwalks for scenic walks. Visitors can enjoy the lush surroundings while soaking in the sun or engaging in local exhibits. The proximity to nudist beaches and the bay adds to the allure of this inviting neighbourhood.

Best time to go to Middle Region

If you're planning a trip to Middle Region, 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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	76.6°F (24.8°C)	No Rain (Dry)	Mostly Sunny	Moderately High	Slightly High
February	76.1°F (24.5°C)	No Rain (Dry)	Mostly Sunny	Moderately High	Average
March	76.3°F (24.6°C)	No Rain (Dry)	Mostly Sunny	Moderately High	Slightly High
April	77.0°F (25.0°C)	No Rain (Dry)	Mostly Sunny	Average	Average
May	78.4°F (25.8°C)	Light Rain	Mostly Sunny	Average	Average
June	79.9°F (26.6°C)	Light Rain	Mostly Sunny	Average	Average
July	80.4°F (26.9°C)	Light Rain	Mostly Sunny	Average	Average
August	81.0°F (27.2°C)	Light Rain	Mostly Cloudy	Moderately Low	Average
September	81.3°F (27.4°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
October	80.8°F (27.1°C)	Light Rain	Mostly Cloudy	Moderately Low	Slightly Low
November	79.5°F (26.4°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
December	78.1°F (25.6°C)	No Rain (Dry)	Mostly Sunny	Average	Slightly High

Booking with Vrbo is simple

Are you hoping to save on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for an extended stay. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and the type of vacation rental you prefer. We're here to help you find the perfect getaway!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers an easy-to-use platform for planning your travel. You can initiate new trips, resume your previous ones, or neatly arrange your travel plans all in one place. Here, you’ll see your saved or booked properties organized into categories like Potential, Upcoming, and Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Middle Region?

In the Middle Region of Sint Maarten, both apartments and villas are popular vacation rental choices, with several options available in this area. The rentals are often situated close to beautiful beaches and local attractions, providing easy access to the vibrant culture and stunning scenery of the island. Most apartments include amenities such as fully equipped kitchens, spacious living areas, and balconies or terraces to enjoy the tropical climate. Similarly, the villas typically offer more extensive facilities, including private pools, gardens, and multiple bedrooms, making them ideal for families or larger groups seeking a luxurious getaway.

How much does it cost to rent a vacation home in Middle Region?

Prices for vacation rentals in Middle Region 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. Vrbo offers something for every taste and budget, from affordable rentals in Middle Region to more spacious homes.

Are there any discounts for Middle Region vacation house rentals?

You can find great discounts on house rentals in Middle Region 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.

Are there any Middle Region vacation rentals with parking?

Vrbo offers a wide selection of vacation rentals in Middle Region 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.

Can I find long-stay vacation rentals in Middle Region?

A long-stay vacation rental in Middle Region 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 any remote work vacation rentals in Middle Region?

In the Middle Region of Sint Maarten, there are several vacation rentals suitable for remote work. This area offers a blend of natural beauty and modern amenities, making it an attractive choice for those looking to balance work and leisure. Many properties come equipped with reliable Wi-Fi, dedicated workspaces, and comfortable living areas, allowing for productivity during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.

How early should I book a Middle Region vacation rental?

Book your Middle Region vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

What are the top attractions in Middle Region?

In the Middle Region of Sint Maarten, visitors can explore a variety of attractions that showcase the island's natural beauty and cultural heritage. Philipsburg, the capital, is known for its vibrant boardwalk and duty-free shopping, offering access to local markets and historical sites like Fort Amsterdam. Vacation rentals in this area often provide easy access to the beach, making it ideal for sunbathers and water sports enthusiasts.

In the nearby Simpson Bay, travellers can enjoy the lively atmosphere filled with restaurants, bars, and a marina, great for those looking to indulge in nightlife or partake in various water activities. The area is also close to Simpson Bay Beach, where visitors can relax on the sand or enjoy water sports.

Can I change or cancel my Middle Region home rental booking on Vrbo?

To find Middle Region vacation 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 Middle Region vacation 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.