South Side Holiday Rentals
- St. Thomas
- ·
- Estate Lovenlund
- 0.28 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
- St. Thomas
- ·
- Estate Lovenlund
- 0.23 mi to center
- Pool
- Balcony/Terrace
- Parking
- Air Conditioner
- St. Thomas
- ·
- Estate Frenchman Bay
- 0.31 mi to center
- Ocean View
- Balcony/Terrace
- View
- Kitchen
- St. Thomas
- ·
- Green Cay Plantation
- 0.11 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Cabes Point
- 0.35 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- St. Thomas
- ·
- Red Hook
- 0.36 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Estate Peterborg
- 0.21 mi to center
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Estate Peterborg
- 0.10 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Pool
- St. Thomas
- ·
- Frydendal
- 0.26 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
Luxury Holiday Rentals in South Side
- St. Thomas
- ·
- Frydendal
- 0.11 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
- St. Thomas
- ·
- Frydendal
- 0.10 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
- St. Thomas
- ·
- Frydendal
- 0.10 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
- St. Thomas
- ·
- Frydendal
- 0.08 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
- St. Thomas
- ·
- Frydendal
- 0.11 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
- St. Thomas
- ·
- Frydendal
- 0.09 mi to center
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
- St. Thomas
- ·
- Estate Bakkero
- 0.22 mi to center
- Oceanfront
- Hot Tub
- Pool
- Ocean View
- St. Thomas
- ·
- Estate Peterborg
- 0.05 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- St. Thomas
- ·
- Green Cay Plantation
- 0.29 mi to center
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
Top-Rated Holiday Rentals with a Pool in South Side
- St. Thomas
- ·
- Red Hook
- 0.31 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Red Hook
- 0.34 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Red Hook
- 0.30 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- St. Thomas
- ·
- Frydendal
- 0.12 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Red Hook
- 0.35 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- St. Thomas
- ·
- Red Hook
- 0.32 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- St. Thomas
- ·
- Red Hook
- 0.38 mi to center
- Private Pool
- Hot Tub
- Pool
- Ocean View
- St. Thomas
- ·
- Red Hook
- 0.34 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- St. Thomas
- ·
- Red Hook
- 0.34 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
Pet-Friendly Holiday Rentals in South Side
- St. Thomas
- ·
- Red Hook
- 0.35 mi to center
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
- St. Thomas
- ·
- Estate Annas Retreat
- 0.43 mi to center
- Pet Friendly
- Parking
- Internet
- Child Friendly
- St. Thomas
- ·
- Red Hook
- 0.21 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Mafolie
- 0.19 mi to center
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
- St. Thomas
- ·
- Estate Charlotte Amalie
- 0.45 mi to center
- Pet Friendly
- Parking
- Internet
- Child Friendly
- St. Thomas
- ·
- Nazareth
- 0.38 mi to center
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
- St. Thomas
- ·
- Estate Bakkero
- 0.27 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
- St. Thomas
- ·
- Frydendal
- 0.37 mi to center
- Oceanfront
- Hot Tub
- Pool
- Ocean View
- St. Thomas
- ·
- Frydendal
- 0.08 mi to center
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
Large Holiday Rentals and Private Villas in South Side
- St. Thomas
- ·
- Frydendal
- 0.29 mi to center
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Estate Wintberg
- 0.35 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- U.S. Virgin Islands
- ·
- Magens Bay
- 0.58 mi to center
- Pool
- Balcony/Terrace
- Kitchen
- Parking
- St. Thomas
- ·
- Rosendal
- 0.06 mi to center
- Hot Tub
- Ocean View
- Balcony/Terrace
- View
- St. Thomas
- ·
- Estate Peterborg
- 0.68 mi to center
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Estate Lovenlund
- 0.27 mi to center
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Cabes Point
- 0.14 mi to center
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Cabes Point
- 0.04 mi to center
- Private Pool
- Oceanfront
- Hot Tub
- Pool
- St. Thomas
- ·
- Estate Lovenlund
- 0.27 mi to center
- Private Pool
- Oceanfront
- Pool
- Ocean View
Wheelchair Accessible Holiday Homes in South Side
- St. Thomas
- ·
- Estate Bolongo
- 0.54 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Anna's Retreat
- 0.18 mi to center
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- St. Thomas
- ·
- Estate Bakkero
- 0.18 mi to center
- Hot Tub
- Spa
- Pool
- Ocean View
- St. Thomas
- ·
- Estate Bakkero
- 0.22 mi to center
- Oceanfront
- Hot Tub
- Pool
- Ocean View
- St. Thomas
- ·
- Estate Bakkero
- 0.37 mi to center
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
- St. Thomas
- ·
- Estate Bakkero
- 0.22 mi to center
- Oceanfront
- Hot Tub
- Pool
- Ocean View
- St. Thomas
- ·
- Estate Bakkero
- 0.22 mi to center
- Oceanfront
- Hot Tub
- Pool
- Ocean View
- St. Thomas
- ·
- Estate Bakkero
- 0.22 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- St. Thomas
- ·
- Estate Frenchman Bay
- 0.37 mi to center
- Oceanfront
- Hot Tub
- Pool
- Ocean View
South Side Private Villas and Holiday Homes Under $200
- St. Thomas
- ·
- Estate Bolongo
- 0.23 mi to center
- Ocean View
- Balcony/Terrace
- View
- Kitchen
- St. Thomas
- ·
- Estate Kings Quarter
- 0.38 mi to center
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
- St. Thomas
- ·
- Estate Charlotte Amalie
- 0.21 mi to center
- Spa
- Balcony/Terrace
- Kitchen
- Parking
- St. Thomas
- ·
- Red Hook
- 0.31 mi to center
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
- St. Thomas
- ·
- Cabes Point
- 0.37 mi to center
- Private Beach
- Oceanfront
- Pool
- Ocean View
- St. Thomas
- ·
- Estate Frenchman Bay
- 0.08 mi to center
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
- St. Thomas
- ·
- Estate Hospital Ground
- 0.24 mi to center
- Ocean View
- Balcony/Terrace
- View
- Kitchen
- St. Thomas
- ·
- Estate Bolongo
- 0.09 mi to center
- St. Thomas
- ·
- Nazareth
- 0.52 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
Instantly Bookable Holiday Homes in South Side
- St. Thomas
- ·
- Red Hook
- 0.30 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- U.S. Virgin Islands
- ·
- South Side
- 0.16 mi to center
- Air Conditioner
- Internet
- Child Friendly
- Laundry
- St. Thomas
- ·
- Red Hook
- 0.34 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- St. Thomas
- ·
- Estate Bolongo
- 0.47 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
- St. Thomas
- ·
- Red Hook
- 0.32 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Red Hook
- 0.32 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Frydendal
- 0.25 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Red Hook
- 0.32 mi to center
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
- St. Thomas
- ·
- Red Hook
- 0.34 mi to center
- Pool
- Ocean View
- Balcony/Terrace
- View
Book a Last Minute Place to Stay in South Side
About Casai's Private Villas and Holiday Rentals in South Side
Discover more than 2295 vacation rentals available in South Side. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in South Side.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in South Side, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near South Side. On average, places to stay near South Side offer 559.8 ft², with nightly prices averaging د.إ.2,321.
With Casai, finding and comparing holiday rentals in South Side is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in South Side
| Type | Count |
|---|---|
| Holiday Apartments | 504 |
| Villas | 250 |
| Vacation Homes | 212 |
| Cottages | 12 |
Use these Quick Filters to Find a Holiday Rental in South Side
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in South Side.
Frequently Asked Questions About South Side?
What are the top holiday rentals in South Side?
With numerous options available in South Side, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday 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
- TreeTops! RedHook! Great Location, View, Pool! Perfect for 2-4 persons!
- DIRECTLY ON SAPPHIRE BEACH, 50 FEET FROM CARIBBEAN SEA ,AWESOME VIEWS OF ST JOHN
- New York Designer's Caribbean Hideaway on Sapphire Beach
- As Seen on HGTV Two Level Renovated Beachfront Villa Generator
How many holiday rentals have private pools in South Side?
Discover a selection of holiday rentals with private pools near South Side with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Salt Life at Sapphire Beach
- The Breeze Villa, A Private Resort
- 37 Steps to the Sea – Oceanfront Ground Floor Paradise w/Backup Generator.
- Sapphire Outlook Villa : Beachfront 2-story Villa on Sapphire Beach, St. Thomas
Which holiday homes in South Side are best for families?
If you're searching for a family-friendly holiday home in South Side, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in South Side:
- Point Pleasant Resort- Luxury Waterfront Villa with Amazing Ocean Views!
- Sapphire Beach 2 bd Condominium w/washer and dryer
- Amazing Views Ocean Front Sapphire Village
How many Casai.ae holiday rentals are available in South Side?
As of 2026, Casai boasts over 2295 properties listed in the South Side area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in South Side.









































































