Discover Your Perfect Philipsburg Vacation Homes

Best Vacation Homes in Philipsburg

Villa
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
8 Bedrooms 2 Baths 16 Guests 14000 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
£1,208/Night 7 Nights - £8,452
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House
Map-icon
like-icon10.0
Exceptional
(14 Reviews)
2 Bedrooms 2 Baths 4 Guests 807.29 ft²
  • Balcony/Terrace
    Balcony/Terrace
  • View
    View
More amenities
£96/Night 7 Nights - £673
House
Map-icon
like-icon8.8
Fabulous
(21 Reviews)
1 Bedroom 1 Bath
  • Pool
    Pool
  • Ocean View
    Ocean View
More amenities
£142/Night 7 Nights - £993
House
Map-icon
like-icon10.0
Exceptional
(11 Reviews)
2 Bedrooms 1 Bath 4 Guests 753 ft²
  • Pool
    Pool
  • Ocean View
    Ocean View
More amenities
£118/Night 7 Nights - £824
House
Map-icon
like-icon10.0
Exceptional
(6 Reviews)
2 Bedrooms 2 Baths 4 Guests 753.47 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
£198/Night 7 Nights - £1,387
Villa
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
3 Bedrooms 3 Baths 6 Guests 1399 ft²
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
£302/Night 7 Nights - £2,115
Apartment
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 4 Guests
  • Kitchen
    Kitchen
  • Parking
    Parking
More amenities
£147/Night 7 Nights - £1,032
Villa
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 3 Baths 6 Guests
  • Pool
    Pool
  • Pet Friendly
    Pet Friendly
More amenities
£320/Night 7 Nights - £2,240

Philipsburg Luxury Rentals

Villa
Map-icon
1 Bedroom 1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£1,731/Night 7 Nights - £12,120
House
Map-icon
8 Bedrooms 8 Baths 20 Guests
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
£1,586/Night 7 Nights - £11,105
Apartment
Map-icon
like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 24 Baths 60 Guests 10763.91 ft²
  • Private Beach
    Private Beach
  • Oceanfront
    Oceanfront
More amenities
£1,335/Night 7 Nights - £9,348
Villa
Map-icon
4 Bedrooms 3 Baths 10 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
£775/Night 7 Nights - £5,428
Villa
Map-icon
4 Bedrooms 3 Baths 10 Guests 1399 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
£774/Night 7 Nights - £5,418
Villa
Map-icon
4 Bedrooms 3 Baths 10 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
£769/Night 7 Nights - £5,384
Villa
Map-icon
4 Bedrooms 3 Baths 10 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
£763/Night 7 Nights - £5,342
Villa
Map-icon
4 Bedrooms 3 Baths 10 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
£753/Night 7 Nights - £5,275

Philipsburg Pet Friendly Vacation Rentals

House
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 3 Baths 6 Guests
  • Pool
    Pool
  • Pet Friendly
    Pet Friendly
More amenities
£292/Night 7 Nights - £2,045
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Apartment
Map-icon
like-icon9.0
Exceptional
(4 Reviews)
1 Bedroom 2 Baths 7 Guests 947.22 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£139/Night 7 Nights - £975
Apartment
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 4 Guests 441 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
£117/Night 7 Nights - £821
star-icons-3
Resort
Map-icon
like-icon8.9
Fabulous
(132 Reviews)
19 Baths 53 Guests 444.91 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
£112/Night 7 Nights - £786
Apartment
Map-icon
like-icon8.0
Excellent
(5 Reviews)
3 Bedrooms 1 Bath 6 Guests
  • Pool
    Pool
  • Pet Friendly
    Pet Friendly
More amenities
£91/Night 7 Nights - £635
Villa
Map-icon
4 Bedrooms 5 Baths 8 Guests 1938 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
More amenities
£323/Night 7 Nights - £2,259
New
Villa
Map-icon
2 Bedrooms 2 Baths 4 Guests
  • Fireplace/Heating
    Fireplace/Heating
  • Pet Friendly
    Pet Friendly
More amenities
£311/Night 7 Nights - £2,175
Villa
Map-icon
2 Bedrooms 3 Baths 4 Guests
  • Pet Friendly
    Pet Friendly
  • Air Conditioner
    Air Conditioner
More amenities
£256/Night 7 Nights - £1,790

Philipsburg Large Vacation Homes

Villa
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 2 Baths 6 Guests
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
£255/Night 7 Nights - £1,787
star-icons-4
Villa
Map-icon
like-icon10.0
Exceptional
(4 Reviews)
2 Bedrooms 2 Baths 4 Guests 1044.1 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
£181/Night 7 Nights - £1,268
Villa
Map-icon
like-icon9.8
Exceptional
(39 Reviews)
2 Bedrooms 2 Baths 6 Guests 1600 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
£286/Night 7 Nights - £2,001
New
Villa
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 2 Baths 4 Guests 753.47 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£141/Night 7 Nights - £989
Villa
Map-icon
like-icon9.6
Exceptional
(30 Reviews)
3 Bedrooms 3 Baths 8 Guests 1600 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
£310/Night 7 Nights - £2,172
Villa
Map-icon
like-icon9.6
Exceptional
(16 Reviews)
5 Bedrooms 5 Baths 14 Guests 3230 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
£628/Night 7 Nights - £4,393
Villa
Map-icon
like-icon8.6
Fabulous
(7 Reviews)
4 Bedrooms 4 Baths 8 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
£488/Night 7 Nights - £3,414
Villa
Map-icon
5 Bedrooms 5 Baths 14 Guests 2476 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
£706/Night 7 Nights - £4,940

Why Choose Rent By Owner for your Philipsburg Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Philipsburg

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit here can enhance your experience, as the best seasons for booking vacation rentals in this destination often align with the region’s climate and local events, ensuring you enjoy optimal weather and vibrant atmosphere during your stay.

Peak Season Highlights

spring
December to April

During the peak season, the region experiences warm, sunny days perfect for enjoying the beaches and outdoor activities, making it an ideal time to book your vacation rentals here.

Average Temperature Daytime: 28°C to 30°C - Nighttime: 22°C to 24°C
spring
July to August

This summer period attracts travelers seeking lively events and vibrant local culture, offering a lively atmosphere in the area with pleasant weather for your stay.

Average Temperature Daytime: 29°C to 31°C - Nighttime: 23°C to 25°C

Off-Season Highlights

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May to June

During these months, the destination tends to be quieter with fewer tourists, providing a peaceful setting for your vacation rentals while enjoying warm weather and lower prices.

Average Temperature Daytime: 27°C to 29°C - Nighttime: 21°C to 23°C
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September to November

This off-peak period sees less traffic due to the hurricane season, but you can still enjoy favorable weather and more affordable rates on your vacation rentals here.

Average Temperature Daytime: 28°C to 30°C - Nighttime: 22°C to 24°C

Weekly Weather Forecast for Philipsburg

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor swimming pool to relax and cool off under the sun.
  • Take advantage of lush gardens or landscaped yards for outdoor leisure and events.
  • Make the most of spacious patios or verandas perfect for outdoor dining and entertaining.
  • Experience outdoor grilling areas or barbecue facilities for delicious meals al fresco.
  • Benefit from direct access to nearby beaches or beachfronts for morning walks and water activities.
  • Utilize outdoor shower amenities to rinse off after a day at the beach or pool.
  • Relax in shaded gazebo areas or lounge zones designed for enjoying the warm Caribbean breeze.
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Family Activities

  • Fort Amsterdam Tour: Discover the historic fortress that offers panoramic views of the harbor, providing an educational and scenic experience for your family in this vibrant destination.
  • Beach Day at Great Bay Beach: Relax and play on the soft sands of this popular beach, perfect for building sandcastles, swimming, and enjoying the tropical sunshine with your loved ones.
  • Marina Shopping and Dining: Stroll along the marina to explore local shops and indulge in family-friendly dining options that showcase the area’s Caribbean flavors.
  • Snorkeling Adventures: Explore the colorful underwater world just off the coast, offering an engaging activity suitable for children and adults alike in this island region.
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Adult Activities

  • Sailing and Watersports: You can enjoy the region’s pristine waters by taking part in sailing, jet skiing, or paddleboarding right from the beaches nearby your vacation rental.
  • Shopping at Front Street: Explore a variety of duty-free shops along this bustling street, perfect for finding unique souvenirs and luxury goods during your stay here.
  • Visiting the Historical Forts: Discover the area's rich history by touring well-preserved forts that offer panoramic views and fascinating insights into the region's past.
  • Dining Experiences: Savor diverse culinary delights at local restaurants offering Caribbean flavors and international cuisine, all within easy reach from your accommodation.

Philipsburg Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Beaches: Make the most of your stay by visiting the area's renowned beaches, where you can relax and enjoy the stunning Caribbean scenery right from your vacation rentals.
  • Try Local Cuisine: Savor authentic flavors at local eateries or in your rental’s kitchen, immersing yourself in the region's vibrant culinary scene.
  • Discover Water Activities: Take advantage of the warm waters by engaging in water sports and excursions that showcase the beauty of this destination’s coastline.
  • Plan Excursions and Tours: Enhance your trip by booking guided tours or day trips through your accommodation to explore the best sights this area has to offer.

Transportation Options

  • Rental Car Services: You can easily explore the area with local rental car agencies offering flexible options to suit your travel plans.
  • Taxis and Ride-Sharing: Taxis and ride-sharing apps provide convenient transportation, allowing you to navigate here comfortably and efficiently.
  • Buses and Public Transit: Affordable public transit options are available for getting around the region and exploring nearby attractions.
  • Charter Boats and Water Taxis: For a scenic experience, water taxis and charter boats offer a unique way to enjoy the coastline and neighboring islands.

Local Customs Options

  • Carnival Celebrations: You can experience vibrant and lively Carnival festivities that showcase the region's rich cultural heritage through colorful parades and traditional music.
  • Local Cuisine Tasting: Sampling regional delicacies, especially fresh seafood and Caribbean-inspired dishes, offers a delightful insight into the area's culinary customs.
  • Respect for Heritage Sites: Visiting and respecting historical landmarks is an important local custom that reflects pride in the region's diverse history.
  • Greetings and Social Etiquette: Embracing the friendly and warm approach of locals through casual greetings and polite interactions enhances your connection with the community here.

Frequently Asked Questions About Philipsburg?

1. What are the top vacation rentals in Philipsburg?

2. How many vacation rentals have private pools in Philipsburg?

There are 35 vacation rentals with private pools near Philipsburg. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Philipsburg are best for families?

If you are looking for a family-friendly vacation home in Philipsburg, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Philipsburg:

4. How many Rentbyowner vacation rentals are available in Philipsburg?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 181 in the Philipsburg area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Philipsburg. 

5. What is the cancellation policy for vacation rentals in this destination?

Cancellation policies vary by property listing, so it's important to review the specific terms outlined in each rental's description. For details on refundable deposits, free cancellation periods, and any applicable fees, please refer to the individual property listing or contact the owner directly.

6. Are there any additional fees I should be aware of when booking a vacation rental here?

Additional fees such as cleaning charges, service fees, or local taxes may apply depending on the property. These details are typically disclosed during the booking process or listed explicitly in the property description, so reviewing the listing carefully will ensure you understand all costs upfront.

7. How do I know if a vacation rental in this area is suitable for my needs?

Property listings include detailed descriptions, photos, and amenities to help you determine suitability. If you need more specific information or have special requirements, reaching out directly to the owner can provide further clarity and assurance before booking.

8. What is the process for checking in and out of a vacation rental in this region?

Check-in and check-out procedures vary among properties. Many rentals offer self-check-in options with keyless entry systems, while others may require in-person coordination. Details about arrival times and access instructions are usually provided after booking or upon confirmation from the property owner.

9. Is it necessary to communicate with the property owner before confirming my reservation?

While many listings allow instant booking without prior contact, reaching out to the owner can be helpful for confirming availability, asking specific questions, or clarifying any special requests. Communication prior to booking enhances your experience and ensures the property matches your expectations.

Philipsburg Top Rated Vacation Rentals

star-icons-4
House
Map-icon
like-icon10.0
Exceptional
(4 Reviews)
1 Bedroom 1 Bath 3 Guests 538.2 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
£172/Night 7 Nights - £1,206
Apartment
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 3 Baths 6 Guests 1614.59 ft²
  • Hot Tub
    Hot Tub
  • Pool
    Pool
More amenities
£473/Night 7 Nights - £3,309
Apartment
Map-icon
like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath 2 Guests 937 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£126/Night 7 Nights - £881
star-icons-4
House
Map-icon
like-icon9.9
Exceptional
(7 Reviews)
3 Bedrooms 3 Baths 6 Guests 861.11 ft²
  • Oceanfront
    Oceanfront
  • Spa
    Spa
More amenities
£162/Night 7 Nights - £1,133
Apartment
Map-icon
like-icon9.8
Exceptional
(13 Reviews)
3 Bedrooms 2 Baths 6 Guests 753 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
£116/Night 7 Nights - £808
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House
Map-icon
like-icon9.8
Exceptional
(6 Reviews)
2 Bedrooms 1 Bath 4 Guests 484.38 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
£188/Night 7 Nights - £1,315
star-icons-4
Villa
Map-icon
like-icon9.8
Exceptional
(5 Reviews)
5 Bedrooms 4 Baths 10 Guests 1184.03 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£227/Night 7 Nights - £1,587
Hotel
Map-icon
like-icon9.6
Exceptional
(131 Reviews)
1 Bath
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
£172/Night 7 Nights - £1,207