Trips to South Side

Plan Your Next Trip to South Side and explore unforgettable sights, local flavors, and exciting experiences.

Villa Palmera - 5-Star Modern Tropical Paradise From US $1,593
         

Wild Ginger Villa From US $704
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool
Down Island Dream - your perfect getaway! 1BR/1BA From US $399
         

Luxury Places to Stay in South Side

Over 2220+ Luxury Places to Stay in or Near South Side

Top-Rated Vacation Rentals with a Pool in South Side

Over 1565+ Top-Rated Vacation Rentals with a Pool in or Near South Side
Island Time on Sapphire Beach, Beach level walkout, Bldg A From US $410
         

On The Beach, Few Steps To The Ocean unit D-204 From US $328
         

10.0 (221 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Paradise For The Two Of You Or Your Family. From US $455
         

10.0 (219 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in South Side

Over 81+ Pet-Friendly Vacation Rentals in or Near South Side
Come Chill on the Hill From US $110
         

10.0 (2 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Security/Safety
Villa Marina Vista From US $470
         

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9.6 (50 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Little Indigo Apartment #2 with BIG Harbor View From US $425
         

6.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
PROMO 5% WEEKLY AND 10% MONTHLY DISCOUNT 4 bedrooms with great views From US $515
         

Villa Mas: Also available as a 3 bedroom. From US $1,293
         

10.0 (96 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Exquisite Paradise View Condo From US $461
         

10.0 (5 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in South Side

Over 345+ Large Vacation Homes & Villas in or Near South Side
Wintberg Tropical Villas From US $225
         

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9.7 (38 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Private villa w/5 oceanfront suites, heated pool From US $1,705
         

Wheelchair Accessible Vacation Homes in South Side

Over 306+ Wheelchair Accessible Vacation Homes in or Near South Side
The Westin St Thomas Beach Resort & Spa From US $324
         

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8.4 (144 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Marriott's Frenchman's Cove From US $1,203
         

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9.0 (193 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Sea You Soon Retreat+Jeep option From US $354
         

10.0 (1 Review)
Condo
  • Air Conditioner
  • Parking
  • Pool

South Side Varoom and Airbnb Places to Stay Under $200

Over 257+ South Side Varoom and Airbnb Places to Stay Under $200
Hidden Hilltop Treasure From US $95
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Flamboyan on the Bay Resort and Villas From US $175
         

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8.6 (829 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pool
Mermaid Hideaway Regatta Point Studio Condo From US $197
         

10.0 (16 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Seahorse:1 Queen Bed From US $183
         

10.0 (16 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in South Side

Over 1250+ Instantly Bookable Vacation Homes in or Near South Side
Beach Front Villa with Down Island View - Priceless! From US $441
         

Our Home is Your Home in St Thomas, ~USVI~ From US $321
         

9.4 (103 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
RENOVATED, Large 1 BDRM, Luxurious, BEACHFRONT. From US $572
         

9.8 (110 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Beautiful Oceanfront Condo From US $307
         

9.8 (39 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Two bedroom beachfront condo at Sapphire Beach! From US $546
         

9.8 (213 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

About South Side Vacation Rentals

With more than 2229 South Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Smartours and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in South Side.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Smartours South Side, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in South Side. Places to stay near South Side are 550.35 ft² on average, with prices averaging $645 a night.

Smartours makes it easy and safe to find and compare vacation rentals in South Side with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in South Side

Type Count
Holiday Apartments 477
Villas 247
Resorts 246
Vacation Homes 206
Hotels with Suites 43
Cottages 11
B&B 5
Others 2
Cabin Rentals 1
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in South Side

Pro Tip: Smartours makes it easy to compare the best listings on Smartours homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Smartours homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in South Side.

Weather in South Side

View the weather forecast for South Side before booking your South Side Vacation Rentals to confirm your best time to go.

December - February
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March - May
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June - August
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September - November
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