Philipsburg vacation rentals

We found 3,147 vacation rentals — enter your dates for availability

Discover a selection of 75 apartments, 36 condos, and other vacation rentals in Philipsburg that are perfect for your trip. Whether you're staying in a vacation rental with family or friends, you'll find the amenities you need and want, which might include parking and a washer and dryer. You'll be sure to find a rental to meet everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Philipsburg

Showing deals for:Jun 12 - Jun 19

Image gallery for 3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at 250/nt!!

Drone view of beach, pool & deck, tiled patio with table and umbrella & garden.
10 out of 10, Exceptional, (110 reviews)
Exceptional
(110 reviews)

3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at 250/nt!!

Simpson Bay

9% off
Price is $257
$1,799 for 7 nights
All fees included
3 BR/3 bath. Sint Maarten DIRECT BEACHFRONT WITH POOL! Rates start at 250/nt!!

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Find out more about Philipsburg

Why visit Philipsburg

  • Historic Attractions: Visit landmarks like the Fort and experience the rich history of Philipsburg.
  • Beautiful Beaches: Relax on stunning Caribbean beaches, perfect for sunbathing and water activities.
  • Vibrant Boardwalk: Stroll along the lively Philipsburg Boardwalk filled with shops and local cuisine.
  • Outdoor Adventures: Enjoy various outdoor activities, from snorkeling to hiking in breathtaking scenery.
  • Diverse Accommodations: Choose from cozy condos to luxurious villas for a perfect stay.

Popular types of accommodation in Philipsburg

Discover the charm of Philipsburg with a variety of vacation rentals to suit every traveler. Whether you're looking for cozy condos, luxurious villas, or spacious apartment rentals, our platform has you covered. From Philipsburg hotels to home rentals, you'll find the perfect accommodation for an unforgettable getaway. Explore your options and enjoy a stay that fits your needs and budget.

  • Condos: The top choice for visitors in Philipsburg, condos offer modern amenities and stunning views, perfect for a relaxing getaway.
  • Villas: A luxurious option, villas provide spacious living and private outdoor spaces, ideal for families or groups seeking comfort.
  • Apartments: Often centrally located, apartments are a practical choice for those wanting easy access to local attractions.
  • Houses: These homes offer a homely atmosphere, suitable for families or friends wanting to enjoy their own space.
  • Guest Houses: For a more personal touch, guest houses provide cozy accommodations and a chance to connect with local culture.**

Top attractions in Philipsburg

Philipsburg, Sint Maarten, offers a delightful blend of beach relaxation and outdoor adventures, making it perfect for travelers seeking scenic beauty and cultural experiences. Explore popular attractions like the historic Fort and the vibrant Philipsburg Boardwalk, or enjoy a day at the beach and marina. Whether you're looking for a leisurely stroll or an adventurous outing, this charming destination has something for everyone.

  • Great Bay Beach: A beautiful stretch of soft sand and crystal-clear waters, Great Bay Beach offers a perfect spot for sunbathing and swimming. Its vibrant atmosphere is enhanced by nearby restaurants and bars, making it a great place to relax and enjoy beach vibes.
  • Fort Amsterdam: This historic fort provides a glimpse into the island's colonial past, featuring stunning views of the coastline. With its rich culture and well-preserved architecture, Fort Amsterdam is a must-visit for history enthusiasts.
  • Philipsburg Courthouse: An architectural gem, this courthouse reflects the island's heritage. Its charming design and cultural significance make it a great photo opportunity and a spot to learn about local governance.

Things to do recommended for couples

In Philipsburg, enjoy a romantic sunset cruise along the coast, explore the charming streets lined with local shops, or unwind on the beautiful beaches. For a special evening, savor a candlelit dinner at a beachfront restaurant, creating lasting memories with your loved one.

Things to do recommended for families

Families visiting Philipsburg can spend a fun-filled day at Kim Sha Beach, where kids can swim and build sandcastles. Explore the St. Maarten Zoo for a close-up look at exotic animals and enjoy a family-friendly meal at one of the many beachfront restaurants.

Things to do recommended for groups

Explore the vibrant local markets in Philipsburg, where you can shop for unique souvenirs and sample traditional Caribbean cuisine. Enjoy a group snorkeling tour to the stunning reefs or relax on the beautiful beaches while soaking up the sun together.

*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 Philipsburg

If you're traveling with a group, family, or pets, or if you’re planning an extended stay, be sure to use the appropriate filters to prioritize your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Philipsburg with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Philipsburg with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with amenities suitable for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Philipsburg: For many families, a trip isn't truly fulfilling without their furry companion. If that resonates with you, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Philipsburg: If you're seeking vacation rentals with 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 rental options. Don’t forget to include additional amenities in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay in Philipsburg

Philipsburg, Sint Maarten, offers an idyllic Caribbean getaway with its stunning beaches and vibrant outdoor activities. Explore downtown Philipsburg, where charming shops and delicious local cuisine await. Just minutes away, you'll find breathtaking scenery and romantic spots perfect for excursions. This destination promises an unforgettable blend of relaxation and adventure, making it the ideal place to unwind and soak in the genuine Caribbean vibes.

  • Upper Prince's Quarter: Nestled in the enchanting area of Philipsburg, Upper Prince's Quarter is a charming village that invites travelers to immerse themselves in its stunning natural landscapes and vibrant atmosphere. Known for its beautiful beaches and scenic views, visitors can enjoy a plethora of outdoor activities. The area boasts convenient access to shopping areas and upscale resorts. Local landmarks include both a serene nudist beach and picturesque bay, making it an ideal spot for sunbathing and relaxation. Whether you're looking to unwind or explore, Upper Prince's Quarter offers a delightful blend of adventure and tranquility.
  • Little Bay: Another gem located in Philipsburg, Little Bay is a picturesque village that serves as a perfect getaway for beach lovers and outdoor enthusiasts. The area is renowned for its scenic beauty, with inviting beaches and lush surroundings. Travelers can engage in various activities, from leisurely strolls along the boardwalk to rounds of golf at nearby courses. With its close proximity to nudist beaches and serene bays, Little Bay offers a perfect balance of relaxation and recreation. It's an ideal spot for those looking to soak up the sun while enjoying the vibrant local culture.
  • Downtown Philipsburg: The bustling heart of Philipsburg, Downtown Philipsburg captivates visitors with its vibrant energy and charming atmosphere. This neighborhood is known for its stunning beaches and outdoor experiences, making it a popular destination for travelers. Explore the lively boardwalk, indulge in shopping at local boutiques, or take in the scenic views of the bay. With access to educational venues and attractions, Downtown Philipsburg offers a unique blend of culture and leisure. Whether you're sampling local cuisine or soaking in the sun, this neighborhood promises an unforgettable experience.

Best time to go to Philipsburg

If you're planning a trip to Philipsburg, it's a good idea to check both the weather and property rates. The warmest month is September. Peak season runs in March to April and July, while off-peak times, like February, May and October tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January76.6°F (24.8°C)No Rain (Dry)Mostly SunnyAverageSlightly High
February76.1°F (24.5°C)No Rain (Dry)Mostly SunnySlightly LowAverage
March76.3°F (24.6°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
April77.0°F (25.0°C)No Rain (Dry)Mostly SunnySlightly HighAverage
May78.4°F (25.8°C)Light RainMostly SunnySlightly LowAverage
June79.9°F (26.6°C)Light RainMostly SunnyAverageAverage
July80.4°F (26.9°C)Light RainMostly SunnySlightly HighAverage
August81.0°F (27.2°C)Light RainMostly CloudyAverageAverage
September81.3°F (27.4°C)Light RainMostly SunnyAverageSlightly Low
October80.8°F (27.1°C)Light RainMostly CloudySlightly LowSlightly Low
November79.5°F (26.4°C)Light RainMostly CloudyAverageSlightly Low
December78.1°F (25.6°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We’re here to help you find the perfect getaway.

Unlock savings with One Key

Plan your next group getaway by booking an eligible Vrbo and earn OneKeyCash on your entire reservation. Being the planner definitely has its perks. When you join our travel rewards program, One Key, you’ll gain access to exclusive member discounts and earn OneKeyCash on qualifying bookings. Sign up today and start reaping the savings.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, manage ongoing arrangements, or review your existing bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips for easy access. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Head to the captivating city of Philipsburg

Enjoy the entertainment and other features of Philipsburg. Well known for its beaches, shopping and island views, this romantic city won't disappoint. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Philipsburg

Are you searching for things to do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Philipsburg a one-of-a-kind vacation spot. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Mullet Bay Golf (4.9 mi / 7.9 km)
  • Aurora International Golf Club (11.4 mi / 18.3 km)

Exploring the beaches and other natural features in Philipsburg

Travelers enjoy Philipsburg for its island views and seaside. Whether you're looking for adventure or just want to take in the scenery, Philipsburg is a great place to get outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Maho Beach (4.9 mi / 7.8 km)
  • Great Bay Beach (0.7 mi / 1.1 km)
  • Little Bay Beach (1.2 mi / 1.9 km)
  • Dawn Beach (2.4 mi / 3.9 km)
  • Kim Sha Beach (3.1 mi / 4.9 km)
  • Flamingo Beach (3.2 mi / 5.2 km)

Seasonal weather in Philipsburg

Travelers enjoy Philipsburg for its boating. If you're planning a vacation around warm-weather activities, September, August, October and July are the hottest months to visit, when temperatures average 81°F.

Transportation options to and around Philipsburg

The nearest airport is in Princess Juliana Intl. Airport (SXM), located 4.4 mi (7 km) from the city center. 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 mi (8.1 km) away.

Frequently asked questions

What is the best area to stay in Philipsburg, Sint Maarten when booking a vacation rental?
When considering the best area to stay in Philipsburg, Sint Maarten for a vacation rental, the beachfront neighborhoods are particularly appealing. These areas boast stunning views of the Caribbean Sea and easy access to beautiful sandy beaches, making them ideal for relaxation and water activities.

One popular attraction is the Great Bay Beach, where visitors can enjoy sunbathing, swimming, and a variety of water sports. The nearby Boardwalk offers a vibrant setting with shops, restaurants, and bars, providing a superb blend of leisure and local culture. Additionally, the historic Fort Amsterdam is close by, offering visitors a glimpse into the island's rich history along with panoramic views of the harbor.

Overall, Philipsburg has a range of vacation rental options, particularly along the waterfront, where you can find a mix of cozy apartments and luxurious villas.
How much does it cost to rent a vacation home in Philipsburg?
Prices for vacation rentals in Philipsburg 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 Philipsburg 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 Philipsburg vacation house rentals?
You can find great discounts on house rentals in Philipsburg 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 Philipsburg?
For renting a beach house in Philipsburg, the area along Great Bay Beach is an excellent choice. This stretch of coastline is known for its soft white sand and clear turquoise waters, making it a prime location for beachside accommodations. Many properties here come with amenities such as private balconies or terraces that offer stunning ocean views, outdoor seating areas, and easy access to the beach. Some rentals may also include features like pools, barbecue facilities, and kitchenettes, ideal for families or groups looking to enjoy the sun and surf.

Additionally, the nearby Little Bay area provides another fantastic option, where vacation rentals often feature direct beach access and amenities like water sports equipment, making it easy for guests to engage in activities such as snorkeling or kayaking. This area is also close to local shops and dining options, enhancing the convenience for travelers.

For those interested in exploring beyond the beach, Philipsburg's vibrant Front Street is just a short distance away, offering a lively option with shops, restaurants, and cultural experiences. Rentals in this vicinity often have modern furnishings and additional conveniences like air conditioning and Wi-Fi, ensuring a comfortable stay while being close to the action.
Are there any houseboat rentals in Philipsburg?
Yes, Philipsburg offers houseboat rentals, providing a unique way to experience the island's vibrant setting and stunning waterfront views. These houseboats are typically located near the bustling beaches and close to attractions like Fort Amsterdam and the Great Bay Beach. Travelers can expect amenities such as comfortable sleeping quarters, kitchen facilities for meal preparation, and outdoor decks for enjoying the sun and sea breeze.
What is the most popular type of vacation rental accomodation in Philipsburg?
In Philipsburg, villas are the most popular type of vacation rental, with about 78 options available throughout the area. These luxurious properties often feature private pools, expansive outdoor terraces, and breathtaking views of the Caribbean Sea, making them ideal for travelers seeking a relaxing getaway. Many villas come equipped with fully furnished kitchens, spacious living areas, and multiple bedrooms, accommodating both small and large groups comfortably.

Apartments follow closely, with around 54 available, typically located near the beach and the vibrant shopping areas of Front Street. Most apartments provide essential amenities such as kitchens, cozy living spaces, and some even include balconies for enjoying the ocean breeze. Additionally, there are about 23 condos that offer similar amenities, often with added features like resort-style pools and fitness centers.

For those seeking a more great experience, there are several vacation houses and houseboats, though these are less common.
Are there any family house rentals in Philipsburg?
In Philipsburg, Sint Maarten, there are a variety of family-friendly house rentals available, with around 78 options to choose from. This charming area is known for its beautiful beaches and vibrant culture, making it an ideal destination for families. Many of these homes feature spacious living areas, full kitchens superb for preparing meals together, and outdoor spaces for relaxation or play.

Visitors can enjoy amenities such as private pools, game rooms for entertainment, and convenient access to nearby attractions like Great Bay Beach and the historic Fort Amsterdam. The town's lively option and local markets offer a great opportunity to experience the island's unique flavors and crafts.
Can I rent a vacation home with a pool or hot tub in Philipsburg?
In Philipsburg, Sint Maarten, there are plenty of vacation homes available for rent that feature pools and hot tubs, with around 110 options to choose from. This picturesque town offers a range of properties located near the beautiful beaches and vibrant downtown area. Travelers can expect amenities such as private pools, relaxing hot tubs, spacious outdoor terraces, and fully equipped kitchens, making these rentals great for both relaxation and entertaining.
Can I find long-stay vacation rentals in Philipsburg?
A long-stay vacation rental in Philipsburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Philipsburg?
In Philipsburg, travelers can find a variety of pet-friendly house rentals, with around 26 options available. Many of these vacation homes feature amenities such as private pools, spacious outdoor areas, fully equipped kitchens, and comfortable living spaces, making them ideal for families and groups traveling with pets.

The beachfront properties often offer stunning ocean views and direct access to sandy shores, while those located in more residential areas provide a tranquil atmosphere with nearby conveniences. Philipsburg's vibrant setting, with its local shops and restaurants, ensures that you have everything you need within reach.

For pet owners, the nearby Great Bay Beach is a superb spot to enjoy the sun and surf, and there are several parks in the area where pets can roam freely.
Are there any remote work vacation rentals in Philipsburg?
In Philipsburg, Sint Maarten, there are numerous options for remote work vacation rentals, with around 146 available. Many of these properties cater specifically to remote workers, featuring amenities such as free Wi-Fi, dedicated workspaces, and comfortable furnishings that support productivity. Travelers can expect a variety of accommodations, from beachfront condos to spacious villas, often equipped with full kitchens and outdoor areas for relaxation after a day of work.

The vibrant setting of Philipsburg offers not only beautiful beaches but also convenient access to local cafes and restaurants, providing ample opportunities for a change of scenery. Additionally, the area's cultural attractions, such as the historic Fort Amsterdam and the lively Front Street shopping district, make it an appealing spot for those looking to balance work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Philipsburg vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Philipsburg with parking available—perfect for families or travelers 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 Philipsburg?
In Philipsburg, popular vacation rental amenities cater to travelers looking for comfort and convenience. Most rentals include a fully equipped kitchen, allowing guests to prepare their own meals and enjoy dining in. Many properties also offer onsite parking, which is a significant advantage for those traveling with a vehicle. Balconies are common, providing a lovely outdoor space to relax and take in the stunning views of the Caribbean Sea. For caffeine lovers, rentals often come with a coffee and tea maker. Additionally, private pools are a sought-after amenity, offering a serene spot for guests to unwind and enjoy the tropical climate.
When is the best time to visit Philipsburg for a vacation rental?
The best time to book a vacation rental in Philipsburg is during the peak season from July to September, when the island is alive with vibrant energy and countless activities. This is the ideal period for travelers seeking sunny beaches, crystal-clear waters, and a plethora of water sports. Visitors can enjoy snorkeling and diving in the warm Caribbean waters while soaking in the picturesque views of the coastline.

July, in particular, stands out as the most popular month to visit Philipsburg, attracting both adventure seekers and families alike. With average temperatures hovering in the mid-80s Fahrenheit, the weather is superb for lounging on the beach or exploring the charming streets of the town. The lively option is enhanced with local festivals and events, offering a rich cultural experience.

For those looking for a more budget-friendly option, February presents a wonderful opportunity to visit Philipsburg. This month falls within the low season, providing visitors with the chance to enjoy quieter beaches and less crowded attractions. With pleasant temperatures in the low 80s Fahrenheit, it is a great time to explore the island's natural beauty without the hustle and bustle of the peak months.

Ultimately, the best time to visit Philipsburg depends on your preference for lively beach experiences or a more tranquil getaway.
How early should I book a Philipsburg vacation rental?
Book your Philipsburg 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 Philipsburg, Sint Maarten?
In Philipsburg, visitors can enjoy a variety of attractions that showcase the island's rich culture and beautiful landscape. The Great Bay Beach is a major draw, offering soft sands and crystal-clear waters, great for sunbathing and water sports. Along the beach, the vibrant boardwalk is lined with shops, restaurants, and bars, providing a lively option.

The historic Philipsburg Fort, built in the 18th century, offers stunning views of the harbor and is a great spot for history enthusiasts. Nearby, the Sint Maarten Museum provides insights into the island's history and culture, making it a worthwhile stop for those interested in learning more about the area.

For shopping enthusiasts, Front Street is a must-visit, featuring a range of duty-free shops and boutiques. Additionally, visitors can explore the local cuisine at various eateries offering fresh seafood and Caribbean dishes.

Nature lovers can venture to the nearby Great Salt Pond or take a short trip to explore the natural beauty of the island, including its hiking trails and scenic viewpoints.
Can I change or cancel my Philipsburg home rental booking on Vrbo?
To find Philipsburg 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Philipsburg 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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