Southside holiday rentals

We found 3,500 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Southside by choosing from 29 houses, 238 flats and other holiday rentals. Whether you’re staying in a holiday home with family or friends, you'll have the amenities that you expect and more, such as Wi-Fi and cable TV. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Popular Southside destinations on Stayz

Holiday rentals with weekly discounts – Southside

Showing deals for:13 Nov - 20 Nov

Main level living room
Outdoor entertainment area
Patio off main level
Main level dining
Exceptional
(43 reviews)

Minutes from Magens Bay, gated property, large pool & outdoor entertainment area

St. Thomas

8% off
AU$5,994
for 7 nights, 1 home
AU$856 per night
includes taxes & fees
Minutes from Magens Bay, gated property, large pool & outdoor entertainment area
Exterior
Incredible view of Caribbean Sea.
View of Caribbean Sea from the comfort of your bed. ☺️
Pathway to the airstream 😎
Exceptional
(33 reviews)

Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

St. Thomas

9% off
AU$1,253
for 7 nights, 1 home
AU$179 per night
includes taxes & fees
Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets
Living area
Living area
Living area
Exterior
Exceptional
(41 reviews)

Blue Serenity - Luxury, Oceanfront, Private Beach Access and Pool

St. Thomas

8% off
AU$18,344
for 7 nights, 1 villa
AU$2,621 per night
includes taxes & fees
Blue Serenity - Luxury, Oceanfront, Private Beach Access and Pool
Room
Down Island View!
Kitchen/Dining
Ocean View from your deck
Exceptional
(9 reviews)

Remodeled Corner Unit D211 with washer & dryer. Sleeps 4

St. Thomas

8% off
AU$5,287
for 7 nights, 1 apartment
AU$755 per night
includes taxes & fees
Remodeled Corner Unit D211 with washer & dryer. Sleeps 4
Pool
Dining
Interior
Room
Exceptional
(7 reviews)

Oceanfront Sunrise Escape + Backup Power & 3 Pools

St. Thomas

8% off
AU$2,399
for 7 nights, 1 apartment
AU$343 per night
includes taxes & fees
Oceanfront Sunrise Escape + Backup Power & 3 Pools
Living area
Outdoor dining
Pool
Dining
Exceptional
(17 reviews)

The Villa Michelle•Luxury•Ocean Views•Heated Salt Pool•Outdoor Living

St. Thomas

8% off
AU$11,833
for 7 nights, 1 villa
AU$1,690 per night
includes taxes & fees
The Villa Michelle•Luxury•Ocean Views•Heated Salt Pool•Outdoor Living
Relax reading a book on the bench with 
ocean splashing in the background.
Areal view og Cowpet Bat West.
Living area
Rainbow from terrace and the dock below
at the St. Thomas Yacht Club.
Exceptional
(82 reviews)

BELLA VISTA Villa - Cowpet Bay West; Beach, Pool, Restaurants, Views, & Breezes

St. Thomas

8% off
AU$5,584
for 7 nights, 1 apartment
AU$798 per night
includes taxes & fees
BELLA VISTA Villa - Cowpet Bay West; Beach, Pool, Restaurants, Views, & Breezes
Entrance
Ahhh...
Abi Beach below-beach bar and restaurant
Kitchen
Exceptional
(152 reviews)

Private Paradise! One level, panoramic views from every room!

St. Thomas

8% off
AU$9,398
for 7 nights, 1 villa
AU$1,343 per night
includes taxes & fees
Private Paradise! One level, panoramic views from every room!
Interior
Pool
Private kitchen
Dining
Exceptional
(96 reviews)

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

St. Thomas

8% off
AU$4,237
for 7 nights, 1 apartment
AU$605 per night
includes taxes & fees
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
Private kitchen
Deck at night
Dining table
Pool at night (Old pool look)
Exceptional
(70 reviews)

3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor

St. Thomas

8% off
AU$6,822
for 7 nights, 1 home
AU$975 per night
includes taxes & fees
3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor
Interior
Property grounds
Dining
Pool
Exceptional
(9 reviews)

Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!

St. Thomas

8% off
AU$2,872
for 7 nights, 1 apartment
AU$410 per night
includes taxes & fees
Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
Hummingbirds flock these flowers
From the balcony
Fully equipped kitchen
Overlooking the ocean
Exceptional
(41 reviews)

Affordable, oceanfront and walk to private beach gem

St. Thomas

8% off
AU$3,714
for 7 nights, 1 apartment
AU$531 per night
includes taxes & fees
Affordable, oceanfront and walk to private beach gem
Mimosas, anyone?
Welcome to our slice of paradise!
Evening Cocktails......can't beat that view!
Property grounds
Steps, literally steps, to the beautiful waters of the Caribbean
Exceptional
(10 reviews)

Carribean Sea Just Steps from Your Patio!!

St. Thomas

8% off
AU$4,015
for 7 nights, 1 apartment
AU$574 per night
includes taxes & fees
Carribean Sea Just Steps from Your Patio!!
Interior
Exterior
Interior
Exterior detail
Exceptional
(19 reviews)

Modern Cozy Studio 🎨 Shopping 🛍Historical 10 minute drive to 🏖

St. Thomas

7% off
AU$1,887
for 7 nights, 1 apartment
AU$270 per night
includes taxes & fees
Modern Cozy Studio 🎨 Shopping 🛍Historical 10 minute drive to 🏖
Private kitchen
Property grounds
Exterior
Villa from the pond in kayak
Exceptional
(18 reviews)

"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.

St. John

9% off
AU$3,975
for 7 nights, 1 villa
AU$568 per night
includes taxes & fees
"Villa Isabelle"-2bed 2 bath, Chocolate Hole on pond Ocean view manicured yard.
Terrace level pool (one of 3 on the property including the ocean level pool)
The view looking out from living room
First bedroom has a  king sized bed, ac, flat screen tv, bathroom
Private kitchen
Exceptional
(166 reviews)

Stunning Ocean Views! Walk To Beaches/Beach Bars/Restaurants

St. Thomas

8% off
AU$3,899
for 7 nights, 1 villa
AU$557 per night
includes taxes & fees
Stunning Ocean Views! Walk To Beaches/Beach Bars/Restaurants
The Beach Bar with live music and grill on the property
Pool
The patio and beach right in front of you!
Socially distancing beach bar area for taking a drink or lunch to the beach
Exceptional
(65 reviews)

Beach, Bed and Beyond! WiFi included , New Tiled Shower!

St. Thomas

9% off
AU$3,866
for 7 nights, 1 apartment
AU$552 per night
includes taxes & fees
Beach, Bed and Beyond! WiFi included , New Tiled Shower!
Main bedroom 2 ( upstairs)
Property grounds
Cliff and ocean view from main bedroom 2
Lounge area
Exceptional
(23 reviews)

Villa Mangorosa

St. Thomas

8% off
AU$7,668
for 7 nights, 1 home
AU$1,095 per night
includes taxes & fees
Villa Mangorosa
Resort.  Our condo is right at the tip of the arrow.
Another view of the pool area.
View of condo from front door entrance.
Counter area with smart TV.
Exceptional
(215 reviews)

Oceanfront Ground Floor Condo. 37 Steps to the Water

St. Thomas

8% off
AU$3,673
for 7 nights, 1 apartment
AU$525 per night
includes taxes & fees
Oceanfront Ground Floor Condo. 37 Steps to the Water
Living area
Property grounds
Living area
Interior
Exceptional
(5 reviews)

The Ampersand Sky Villa: Iconic, Artful Luxury

St. Thomas

13% off
AU$4,895
for 7 nights, 1 villa
AU$699 per night
includes taxes & fees
The Ampersand Sky Villa: Iconic, Artful Luxury
Living area
Exterior
Terrace/patio
Interior
Exceptional
(20 reviews)

Home with panoramic views with access to private beach!

St. Thomas

8% off
AU$17,645
for 7 nights, 1 villa
AU$2,521 per night
includes taxes & fees
Home with panoramic views with access to private beach!
Private kitchen
Property grounds
Room
Living area
Exceptional
(12 reviews)

Beautiful Villa on Point Pleasant Resort

St. Thomas

8% off
AU$7,636
for 7 nights, 1 villa
AU$1,091 per night
includes taxes & fees
Beautiful Villa on Point Pleasant Resort
Room
Our Actual Balcony and View of the Amazing Sapphire Beach Marina!
A casually elegant space to enjoy your time at the beach! Photos from Sept 2022!
Apple TV, Netflix App, DVD/BlueRay with movies & 50MB Fiber Internet!
Exceptional
(134 reviews)

5★ Sapphire Dream! Ocean & Marina Views-Sapphire Beach Condo-Luxury Reno!

St. Thomas

8% off
AU$4,080
for 7 nights, 1 apartment
AU$583 per night
includes taxes & fees
5★ Sapphire Dream! Ocean & Marina Views-Sapphire Beach Condo-Luxury Reno!
Room
Interior
Private kitchen
Interior
Excellent
(20 reviews)

Cozy stay, next to lookout and 10 minutes for Magens Bay Beach

St. Thomas

5% off
AU$1,938
for 7 nights, 1 villa
AU$277 per night
includes taxes & fees
Cozy stay, next to lookout and 10 minutes for Magens Bay Beach

Choose a holiday rental for your Southside getaway

Learn about the unique charm of Southside with a stay in a holiday home rental. This city has something for everyone. Sapphire Beach and Trunk Bay are just a couple of the must-see attractions in the area. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Southside

Are you looking for top things to see and do during your stay? Venture out of your cosy holiday rental and check out everything that makes Southside a fun spot to go on holiday. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Mahogany Run Golf Course (2.6 mi / 4.2 km)
  • The Self Centre (7.6 mi / 12.3 km)

Exploring the natural landscape of Southside

Whether you're an active traveller or just want to spend some time taking in the scenery, Southside is a great place to get outside. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Sapphire Beach (3.4 mi / 5.5 km)
  • Trunk Bay (8.8 mi / 14.2 km)
  • Virgin Islands National Park (10.2 mi / 16.4 km)
  • Bolongo Bay (0.7 mi / 1.1 km)
  • Frenchman's Bay (1 mi / 1.5 km)
  • Wyndham Sugar Bay Beach (2.8 mi / 4.5 km)

Frequently asked questions

What is the most popular type of holiday home accommodation in Southside?
Condos are the most popular type of holiday home in Southside, according to our data. Even if you have something different in mind, Stayz has properties in loads of sizes and shapes. Take a look at our options to find your perfect pad.
How much does it cost to rent a holiday home in Southside?
Season, length of stay and property type are among the factors that can determine the price of a holiday home. Simply click on your dates of travel to find your ideal match. From quaint country cottages to sprawling luxury villas, all Stayz holiday homes offer amazing value.
How much does it cost to rent a beach house in Southside?
Prices for beach houses in Southside can differ depending on the size and style of the property and when you plan to travel. Simply enter your dates of travel into Stayz and the number of guests to see your home options and prices. From there you can use our filters to refine your search by amenities, nearby activities, ratings and more.
What are popular home amenities in Southside?
A microwave oven, a fridge and a stovetop head the list of most popular home amenities in Southside. Whether you're heading away on your own, with your other half or as a family group, Stayz will help you find a holiday home that fits your style with all the features you're looking for.
Are there large group holiday homes in Southside?
Take your pick of 17 properties in Southside that can host 10 or more people. Whether you're planning time away with extended family or an event like a party, there's enough room to get your group together under the same roof.
Can I find two-bedroom holiday homes in Southside?
Southside has 152 two-bedroom holiday homes that you can choose from. Experience a holiday home with all the comfort and privacy you need at a fantastic price on Stayz.
Are there holiday homes with WiFi in Southside?
Whether you want to keep up with world events, make a video call or update your social media, there are 96 holiday homes with WiFi in Southside. Check the "WiFi" box when searching on Stayz and stay connected on your getaway.
How old do you have to be to rent a holiday home in Southside?
The minimum age requirements can differ across properties on Stayz, so be sure to check the rules of the holiday home in Southside you're interested in. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Southside for?
The amount of time you can rent a Southside holiday home for depends on each property. Just enter your travel dates to find available options offering extended stays. They feature everything you need to make your extended getaway more enjoyable such as kitchens and laundries. Some Stayz holiday homes may also offer weekly or monthly discounted prices, so you can stick around for longer for less.