Best Vacation Homes in South Side
Condo
10.0(291 Reviews)
1 Bedroom
1 Bath
2 Guests
750 ft²
Fireplace/Heating
Pool
Ocean View
Balcony/Terrace
R5,583/Night
7 Nights - R39,077
Apartment
10.0(4 Reviews)
1 Bedroom
1 Bath
4 Guests
796.53 ft²
Private Beach
Oceanfront- Pool
- Ocean View
R6,450/Night
7 Nights - R45,152
Condo
10.0(271 Reviews)
2 Bedrooms
1 Bath
2 Guests
650 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
R6,288/Night
7 Nights - R44,009
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
3 Guests
Pet Friendly
Parking
Internet
Child Friendly
R1,796/Night
7 Nights - R12,574
Condo
10.0(229 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Pool
- Ocean View
- Balcony/Terrace
View
R5,098/Night
7 Nights - R35,681
Condo
10.0(225 Reviews)
1 Bedroom
1 Bath
4 Guests
750 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R4,911/Night
7 Nights - R34,374
Condo
10.0(220 Reviews)
1 Bedroom
2 Baths
6 Guests
1200 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
R6,855/Night
7 Nights - R47,977
South Side Luxury Rentals
Resort
6.0(2 Reviews)
3 Baths
8 Guests
Hot Tub- Fireplace/Heating
- Pool
Kitchen
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Resort
10.0(1 Review)
3 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
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Resort
8.0(4 Reviews)
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
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Resort
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
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Resort
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
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Resort
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
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Condo
3 Bedrooms
3 Baths
4 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
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New
Boat Rental
4 Bedrooms
5 Baths
8 Guests
172 ft²
- Child Friendly
Security/Safety
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South Side Pet Friendly Vacation Rentals
Villa
10.0(103 Reviews)
4 Bedrooms
4 Baths
10 Guests
3600 ft²
Private Pool- Oceanfront
- Pool
- Ocean View
R21,025/Night
7 Nights - R147,181
Apartment
9.6(38 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Pet Friendly
- Parking
Air Conditioner
R2,498/Night
7 Nights - R17,489
Villa
9.6(54 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R7,675/Night
7 Nights - R53,725
House
10.0(31 Reviews)
3 Bedrooms
3 Baths
7 Guests
2200 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R7,257/Night
7 Nights - R50,802
Apartment
9.6(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
129.17 ft²
- Balcony/Terrace
- View
- Pet Friendly
- Parking
R3,756/Night
7 Nights - R26,291
House
10.0(15 Reviews)
4 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R6,124/Night
7 Nights - R42,866
Condo
10.0(12 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
R11,159/Night
7 Nights - R78,106
Apartment
10.0(9 Reviews)
4 Bedrooms
2 Baths
8 Guests
2400 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
R8,403/Night
7 Nights - R58,820
South Side Large Vacation Homes
Villa
10.0(181 Reviews)
6 Bedrooms
7 Baths
12 Guests
6000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R28,475/Night
7 Nights - R199,322
Villa
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
2497.23 ft²
- Pool
- Balcony/Terrace
- Parking
- Air Conditioner
R11,496/Night
7 Nights - R80,473
Villa
1 Bedroom
1 Bath
- Pool
- Balcony/Terrace
- Kitchen
- Parking
R11,349/Night
7 Nights - R79,445
Villa
10.0(163 Reviews)
4 Bedrooms
4 Baths
8 Guests
4500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R21,129/Night
7 Nights - R147,899
Villa
9.0(3 Reviews)
3 Bedrooms
4 Baths
6 Guests
1797.57 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- View
R13,194/Night
7 Nights - R92,361
Villa
10.0(163 Reviews)
2 Bedrooms
2 Baths
6 Guests
1750 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R6,073/Night
7 Nights - R42,507
House
10.0(155 Reviews)
6 Bedrooms
7 Baths
12 Guests
5000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
R32,055/Night
7 Nights - R224,388
Villa
10.0(153 Reviews)
5 Bedrooms
4 Baths
10 Guests
5000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R25,906/Night
7 Nights - R181,343
Why Choose Rent By Owner for your South Side Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit South Side
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit ensures you experience the best of this destination, allowing you to enjoy favorable weather and optimal conditions for your stay in the area.
Peak Season Highlights
December to April
During the peak season, you’ll experience warm, sunny days ideal for enjoying the region's scenic beauty and outdoor activities. This is when the area’s vacation rentals are in high demand, making it a popular time for travelers seeking the perfect getaway.
Average Temperature Daytime: 80°F - 85°F - Nighttime: 70°F - 75°F
June to August
The summer months attract visitors looking to indulge in the area's vibrant atmosphere and lively events. Expect higher occupancy rates of vacation rentals as many plan their vacations during this lively period in the destination.
Average Temperature Daytime: 85°F - 90°F - Nighttime: 75°F - 80°F
Off-Season Highlights
May to June
Before the summer rush, the region offers a quieter atmosphere with more availability for your preferred vacation rentals. It’s an excellent time to enjoy the area's natural beauty and peaceful surroundings without the crowds.
Average Temperature Daytime: 80°F - 85°F - Nighttime: 70°F - 75°F
September to November
Following the busy summer period, this shoulder season features fewer visitors and more relaxed booking options. The weather remains warm, perfect for exploring or unwinding in your rental here during the quieter months.
Average Temperature Daytime: 80°F - 85°F - Nighttime: 70°F - 75°F
Weekly Weather Forecast for South Side
How to Book Your South Side Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
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.
Explore and book the perfect rental in South Side
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
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 outdoor lounging areas with scenic views to unwind after a day exploring the region.
- Make the most of private pools or plunge pools available at many properties for a refreshing swim.
- Take advantage of well-maintained patios or decks ideal for outdoor dining and entertaining.
- Benefit from lush gardens or landscaped yards that enhance your tropical getaway experience.
- Stay active with access to outdoor sports amenities such as tennis courts or basketball hoops.
- Relax under shaded gazebos or covered terraces perfect for enjoying the warm Caribbean breeze.
- Utilize outdoor BBQ grills to host memorable cookouts amidst the natural beauty surrounding you.
Top Attractions Around South Side
What attractions are nearby?
Near your stay in South Side, you can enjoy a variety of activities such as exploring beautiful beaches, engaging in water sports, or discovering local cultural sites, all conveniently located within this vibrant region.
Family Activities
- Snorkeling at Maho Bay: Discover the vibrant marine life just off the coast, making it an ideal family activity to explore the clear waters of this destination.
- Visit to the Virgin Islands National Park: Enjoy a family-friendly day immersed in nature with scenic hiking trails and educational tours within the region’s protected area.
- Exploring the local beaches: Relax and play on the sandy shores that provide safe swimming and fun-filled activities suitable for children of all ages.
- Water sports adventures: Experience kayaking, paddleboarding, or boat rentals available here, offering engaging ways for families to enjoy the region’s beautiful coastline together.
Adult Activities
- Sailing Tours: Experience the breathtaking waters surrounding this destination on a sailing tour that offers stunning views and a chance to unwind in the region's beautiful marine environment.
- Snorkeling Adventures: Discover vibrant coral reefs and diverse marine life just off the coast, making it a perfect activity for exploring the region’s underwater beauty.
- Local Dining Experiences: Indulge in authentic flavors at nearby restaurants that showcase the region’s culinary heritage, ideal for enjoying evenings after your day of exploration.
- Shopping at Local Markets: Browse unique handcrafted goods and souvenirs in the area’s markets, providing a great opportunity to find memorable keepsakes from your trip.
South Side Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the region’s vibrant culinary scene to enjoy authentic flavors and fresh seafood, enhancing your overall experience here.
- Plan Water-Based Activities: Make the most of the area's stunning beaches by engaging in activities like snorkeling, kayaking, or paddleboarding to fully appreciate the natural beauty.
- Leverage Nearby Attractions: Use your vacation rental as a base to visit nearby points of interest, enriching your stay with memorable excursions around this popular destination.
- Choose Strategic Accommodation Locations: Select a rental that offers convenient access to the region’s key hotspots, ensuring a seamless and enjoyable holiday experience here.
Transportation Options
- Car Rentals: Renting a car here offers you the flexibility to explore the region at your own pace, with many local rental agencies available nearby.
- Taxis and Ride-Sharing Services: Reliable taxis and ride-sharing options are readily accessible for convenient transportation within this destination.
- Public Buses: Affordable and frequent bus services connect key areas of the region, making it easy to get around without a vehicle.
- Bike Rentals: For a scenic and eco-friendly way to see the area, bike rentals are an excellent choice, especially in bike-friendly neighborhoods.
Local Customs Options
- Island Reggae Music: You will notice the vibrant local music scene, especially the prominent reggae rhythms that reflect the area's laid-back and lively spirit.
- Local Craftsmanship: Handcrafted goods such as jewelry and art are commonly sold by local artisans, offering authentic souvenirs that celebrate island culture.
- Traditional Celebrations: Participating in or observing local festivals and parades allows you to experience the region's rich cultural heritage firsthand.
- Seafood Cuisine: The region's culinary traditions emphasize fresh seafood dishes, showcasing the area's connection to the surrounding waters.
Frequently Asked Questions About South Side?
1. What are the top vacation rentals in South Side?
There are a lot of options in South Side. If you plan on staying in the South Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in South Side:
- Island Time Sapphire Beach, Beach level walkout, Bldg A , Backup Generator.
- SEA GLASS at Sapphire Beach Unit E-206 - great views of STJ and BVIs!
- On The Beach, Few Steps To The Ocean unit D-204
- C5 @Point Pleasant Villas 1BR/1BA-Amazing Views & Private Wrap around Balcony
- Beautiful Beachfront Villa On Sapphire Beach with Generator and Dishwasher
- Picture Perfect! Amazing Beachfront Condo with Spectacular Panoramic Views
- New York Designer's Caribbean Hideaway on Sapphire Beach
- TreeTops! RedHook! Great Location, View, Pool! Perfect for 2-4 persons!
- As Seen on HGTV Two Level Renovated Beachfront Villa Generator
- 30 STEPS FROM THE SEA, BEACH LEVEL, QUIET END , AWESOME VIEWS OF ST JOHN
2. How many vacation rentals have private pools in South Side?
There are 234 vacation rentals with private pools near South Side. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in South Side are best for families?
If you are looking for a family-friendly vacation home in South Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in South Side:
4. How many Rentbyowner vacation rentals are available in South Side?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 2301 in the South Side 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 South Side.
5. What is the cancellation policy for vacation rentals in South Side, U.S. Virgin Islands?
The cancellation policy varies by property and owner. Be sure to review the specific policy listed on each property’s page or contact the owner directly to understand any fees or restrictions that may apply.
6. Are there any special requirements or house rules I should be aware of when booking in this region?
Each property in the area has its own set of rules and requirements. It’s recommended to read the listing details carefully and reach out to the owner if you have any questions before confirming your reservation.
7. How do I secure my reservation for a stay here?
Reservations are typically confirmed through a secure booking process on the website. Ensure you provide all necessary information and follow the instructions provided by the platform or property owner to finalize your booking.
8. Is it possible to modify or extend my stay after booking a vacation rental in this destination?
Modifications or extensions depend on the owner’s policies and availability. Contact the property owner directly through the platform to discuss any changes to your original reservation.
9. What amenities are usually included with vacation rentals in this area?
Amenities vary by property, but many include essentials like Wi-Fi, kitchen facilities, and air conditioning. For specific features, check the listing details or contact the owner to ensure the property meets your needs.
South Side Top Rated Vacation Rentals
Condo
10.0(203 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
R6,047/Night
7 Nights - R42,327
Condo
10.0(194 Reviews)
1 Bedroom
2 Baths
4 Guests
1350 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R3,952/Night
7 Nights - R27,663
House
10.0(194 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
R3,735/Night
7 Nights - R26,144
Condo
10.0(193 Reviews)
1 Bedroom
2 Baths
4 Guests
1100 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
R12,019/Night
7 Nights - R84,131
Condo
10.0(193 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
R8,387/Night
7 Nights - R58,706
Condo
10.0(191 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
R6,001/Night
7 Nights - R42,017
House
10.0(190 Reviews)
2 Bedrooms
2 Baths
5 Guests
1740 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R5,739/Night
7 Nights - R40,171
Condo
10.0(187 Reviews)
1 Bedroom
1 Bath
2 Guests
650 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R6,009/Night
7 Nights - R42,066
