Best Vacation Homes in Southside
Villa
10.0(146 Reviews)
3 Bedrooms
3 Baths
6 Guests
5900 ft²
Oceanfront
Pool
Ocean View
Balcony/Terrace
R14,214/Night
7 Nights - R99,495
Resort
9.0(104 Reviews)
14 Baths
42 Guests
378.28 ft²
- Oceanfront
Hot Tub- Pool
- Ocean View
R11,511/Night
7 Nights - R80,575
Villa
10.0(103 Reviews)
4 Bedrooms
4 Baths
10 Guests
3600 ft²
Private Pool- Oceanfront
- Pool
- Ocean View
R19,462/Night
7 Nights - R136,232
Resort
8.3(158 Reviews)
22 Baths
64 Guests
420.31 ft²
- Oceanfront
Spa
Fireplace/Heating- Pool
R5,247/Night
7 Nights - R36,721
Apartment
10.0(92 Reviews)
2 Bedrooms
2 Baths
6 Guests
1500 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R6,780/Night
7 Nights - R47,454
Condo
10.0(83 Reviews)
2 Bedrooms
2 Baths
5 Guests
1260 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R5,305/Night
7 Nights - R37,126
House
10.0(66 Reviews)
3 Bedrooms
3 Baths
6 Guests
2285 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R11,484/Night
7 Nights - R80,381
Southside Luxury Rentals
Condo
3 Bedrooms
3 Baths
4 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
Unlock the Best Price
Villa
9 Bedrooms
8 Baths
18 Guests
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
R110,772/Night
7 Nights - R775,404
Resort
5 Baths
18 Guests
- Fireplace/Heating
Air Conditioner
Child Friendly
Laundry
R89,168/Night
7 Nights - R624,175
Resort
5 Baths
18 Guests
- Fireplace/Heating
- Air Conditioner
Internet- Child Friendly
R81,062/Night
7 Nights - R567,432
House
10.0(8 Reviews)
5 Bedrooms
6 Baths
15 Guests
8500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
R62,365/Night
7 Nights - R436,566
Resort
9.6(13 Reviews)
2 Baths
8 Guests
1179 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
R45,870/Night
7 Nights - R321,085
Resort
3 Baths
12 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
R45,395/Night
7 Nights - R317,762
Resort
3 Baths
12 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
R45,395/Night
7 Nights - R317,762
Southside Pet Friendly Vacation Rentals
House
10.0(31 Reviews)
3 Bedrooms
3 Baths
7 Guests
2200 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R7,204/Night
7 Nights - R50,437
House
10.0(4 Reviews)
5 Bedrooms
3 Baths
14 Guests
Pet Friendly
Kitchen
Parking- Air Conditioner
R9,885/Night
7 Nights - R69,194
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
4 Guests
- Ocean View
- Balcony/Terrace
View- Pet Friendly
R4,629/Night
7 Nights - R32,408
Villa
9.8(66 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
R5,674/Night
7 Nights - R39,720
Apartment
9.6(56 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R2,763/Night
7 Nights - R19,341
Apartment
9.4(18 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Oceanfront
- Ocean View
- View
- Pet Friendly
R2,783/Night
7 Nights - R19,487
Apartment
9.2(38 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R2,751/Night
7 Nights - R19,260
House
9.2(20 Reviews)
4 Bedrooms
3 Baths
8 Guests
3500 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R12,708/Night
7 Nights - R88,957
Southside Large Vacation Homes
Villa
10.0(48 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
R11,966/Night
7 Nights - R83,769
Apartment
3 Bedrooms
3 Baths
10 Guests
1001.04 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R4,253/Night
7 Nights - R29,766
Villa
10.0(31 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R13,480/Night
7 Nights - R94,356
Villa
10.0(21 Reviews)
4 Bedrooms
4 Baths
10 Guests
2000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R12,213/Night
7 Nights - R85,488
Villa
10.0(17 Reviews)
5 Bedrooms
5 Baths
14 Guests
3000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
R27,579/Night
7 Nights - R193,057
Villa
10.0(13 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
R17,132/Night
7 Nights - R119,923
Villa
10.0(6 Reviews)
4 Bedrooms
3 Baths
9 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
R15,796/Night
7 Nights - R110,568
House
10.0(4 Reviews)
3 Bedrooms
3 Baths
12 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
R9,565/Night
7 Nights - R66,957
Why Choose Rent By Owner for your Southside 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 Southside
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit allows you to enjoy the region’s inviting climate and vibrant local culture while making the most of your stay in this popular destination.
Peak Season Highlights
December to April
This is the peak season when the weather in this Caribbean destination is most favorable, attracting visitors seeking sunny days and warm temperatures. During these months, you can enjoy ideal conditions for outdoor activities and water-based adventures.
Average Temperature Daytime: 85°F - Nighttime: 75°F
June to August
The summer months draw many travelers to the area eager to experience the lively atmosphere and vibrant marine life. This period offers long, sunny days perfect for exploring the region's natural beauty and relaxing on the beaches.
Average Temperature Daytime: 88°F - Nighttime: 78°F
Off-Season Highlights
May and November
These shoulder months see fewer visitors, providing a more tranquil experience with less crowding while still enjoying warm weather and calm seas. It’s an excellent time for those looking to escape the busy season without sacrificing pleasant conditions.
Average Temperature Daytime: 83°F - Nighttime: 73°F
September to October
During this off-peak period, the region experiences a slight lull as it falls within the hurricane season. Travel here during this time may offer reduced rates and quieter surroundings, but it's wise to monitor weather forecasts closely.
Average Temperature Daytime: 81°F - Nighttime: 72°F
Weekly Weather Forecast for Southside
How to Book Your Southside 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 Southside
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 a private outdoor pool to relax and unwind in the warm Caribbean sun.
- Take advantage of a spacious patio or deck area perfect for outdoor dining and entertaining.
- Make the most of lush gardens or landscaped yards that enhance the tropical atmosphere.
- Relax in a shaded gazebo or outdoor lounge area, ideal for reading or socializing.
- Benefit from direct access to nearby beaches or waterfront views for scenic strolls.
- Utilize outdoor grilling facilities to prepare delicious meals amidst the island's natural beauty.
- Experience outdoor recreational equipment such as kayaks or snorkel gear, often available at prime locations here.
Top Attractions Around Southside
What attractions are nearby?
In this vibrant area, you can enjoy a variety of activities nearby, from relaxing on stunning beaches to exploring local shops and dining options, making it an ideal destination for your next getaway.
Family Activities
- Coral World Ocean Park: Explore marine life up close with interactive exhibits and underwater observatories that make learning about ocean ecosystems fun for the whole family.
- Bluebeard's Beach: Relax on this family-friendly beach, where gentle waters and soft sands provide the perfect setting for swimming, sunbathing, or building sandcastles.
- Skyride to Paradise Point: Take a scenic cable car ride offering breathtaking views of the harbor and coastline, creating memorable photo opportunities for your family adventure.
- Blackbeard's Castle: Discover the history of the region at this historic site, which combines stunning vistas with engaging stories suitable for all ages.
Adult Activities
- Snorkeling and Scuba Diving: Discover vibrant marine life just off the coast, making it an ideal activity to explore underwater beauty during your stay here.
- Island Hopping Tours: Embark on guided excursions to nearby islands, offering stunning views and unique experiences within this tropical region.
- Sailing Adventures: Enjoy the tranquil waters around the area by chartering a sailing trip that caters to your desire for relaxation and exploration.
- Art Galleries and Cultural Centers: Immerse yourself in local art, history, and culture at various galleries and centers nestled within this destination.
Other Places to Stay in Southside
Estate Bovoni
Mangrove Lagoon
Estate Charlotte Amalie
Estate Hoffman
Havensight
Bellevue
Frenchman's Bay
Estate Bakkero
South Coast
Estate Bolongo
Estate Frenchman Bay
Green Cay Plantation
Southside Travel Tips
How Can You Make the Most of Your Stay?
- Plan your excursions early: Taking advantage of local activities and attractions ensures you experience the best this destination has to offer while making the most of your stay in the region.
- Choose a well-located vacation rental: Staying near key beaches and amenities allows for easy access to the area's top sights, enhancing your overall experience.
- Explore local cuisine: Sampling authentic dishes at nearby restaurants will enrich your visit and provide a better understanding of the island’s culinary culture.
- Respect the environment: Practicing eco-friendly habits helps preserve the natural beauty of the area for future visitors and ensures a sustainable travel experience.
Transportation Options
- St. Thomas Ferry:** This trusted ferry service offers convenient transportation between the island and nearby destinations, ensuring easy access to the region's beautiful beaches and attractions.
- Taxi Services:** Reliable taxi options are readily available in this area, providing quick and comfortable transfers to key spots around Southside and beyond.
- Car Rentals:** Dedicated car rental agencies allow you to explore the region at your own pace, securing economic and flexible transportation directly from the airport or local hubs.
- Public Buses:** Local bus routes offer an affordable way to navigate here, connecting major points of interest and making it simple to move around the area economically.
Local Customs Options
- Local Greetings and Politeness: When visiting here, you’ll notice that greeting with a friendly "hello" or "good morning" is customary and demonstrates respect for the vibrant local culture.
- Dining Etiquette: It’s common to share meals family-style and engage in warm conversations, reflecting the area's emphasis on community and connection.
- Celebration of Festivals: Participating in or observing local festivals is a cherished tradition, offering insights into the region’s rich heritage and lively spirit.
- Respect for Nature and Environment: The residents highly value environmental preservation, so responsible behavior and eco-consciousness are appreciated during your stay in this area.
Frequently Asked Questions About Southside?
1. What are the top vacation rentals in Southside?
There are a lot of options in Southside. If you plan on staying in the Southside area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Southside:
- Private Paradise! One level, panoramic views from every room!
- Villa Mas: Also available as a 3 bedroom.
- Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
- Featured on HGTV! Sea Cliff Villa at Bolongo Bay
- 3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor
- Easy location, Ocean view, Sunsets, Jeep Available, Solar, Battery Power, Wifi
- 4bd 4.5 baths House and two private apartments. Beautiful views! Self check in!
- Darling Palms Tree House: Beachside Studio Oasis
- Marriott's Frenchman's Cove-ALL DATES DIRECT FROM OWNER
- Recently Built! - 3 Bed/3 Bath House with Amazing View & Large Private Deck
2. How many vacation rentals have private pools in Southside?
There are 35 vacation rentals with private pools near Southside. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Southside are best for families?
If you are looking for a family-friendly vacation home in Southside, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Southside:
4. How many Rentbyowner vacation rentals are available in Southside?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 581 in the Southside 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 Southside.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property; you should review the specific listing details or contact the owner directly to understand the terms and any applicable fees before booking.
6. How do I confirm my reservation and what are the payment options?
Reservations are confirmed once you complete the booking process on the platform, and payment methods typically include credit card, debit card, or other secure online payment options specified in the listing.
7. Are there any additional fees I should be aware of when booking vacation rentals here?
Additional fees such as cleaning, service charges, or local taxes may apply; these will be clearly listed during the booking process or detailed in the property description.
8. What amenities are usually available in the vacation rentals in this region?
Most properties offer amenities like Wi-Fi, air conditioning, fully equipped kitchens, and outdoor spaces, but it’s best to check each listing for specific features included.
9. Is there a minimum stay requirement for booking a rental in this destination?
Minimum stay requirements can vary based on the property and season; please refer to the individual listing or contact the owner directly to confirm your desired dates.
Southside Top Rated Vacation Rentals
House
10.0(30 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
R12,159/Night
7 Nights - R85,115
Resort
10.0(29 Reviews)
2 Baths
8 Guests
1245 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
R11,689/Night
7 Nights - R81,824
Condo
10.0(29 Reviews)
3 Bedrooms
2 Baths
6 Guests
900 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R7,132/Night
7 Nights - R49,918
Hotel
10.0(24 Reviews)
2 Baths
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R15,285/Night
7 Nights - R106,985
Condo
10.0(23 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R4,633/Night
7 Nights - R32,425
Apartment
10.0(17 Reviews)
1 Bedroom
1 Bath
3 Guests
500 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R3,665/Night
7 Nights - R25,648
Condo
10.0(14 Reviews)
4 Bedrooms
4 Baths
8 Guests
2600 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R10,117/Night
7 Nights - R70,816
Condo
10.0(12 Reviews)
1 Bedroom
2 Baths
6 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
R4,876/Night
7 Nights - R34,127
