Southside holiday homes

We found 3,550 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Southside by choosing from 30 houses, 253 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 Bookabach

Holiday rentals with weekly discounts – Southside

Showing deals for:25 Dec - 1 Jan

Aerial view
Interior
Room
Interior
Wonderful
(22 reviews)

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

St. Thomas

5% off
NZ$2,359
for 7 nights, 1 villa
NZ$337 per night
includes taxes & fees
Cozy stay, next to lookout and 10 minutes for Magens Bay Beach
Exterior
Incredible view of Caribbean Sea.
Pathway to the airstream 😎
View of Caribbean Sea from the comfort of your bed. ☺️
Exceptional
(33 reviews)

Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets

St. Thomas

9% off
NZ$1,561
for 7 nights, 1 home
NZ$223 per night
includes taxes & fees
Airstream Glamping Camping overlooking Caribbean Sea Amazing Sunrises & Sunsets
Spacious balcony with amzing ocean view
Beach
Living area
Living area
Exceptional
(19 reviews)

Playcation in Paradise villa with endless water view

St. Thomas

12% off
NZ$10,080
for 7 nights, 1 home
NZ$1,440 per night
includes taxes & fees
Playcation in Paradise villa with endless water view
Hummingbirds flock these flowers
From the balcony
Overlooking the ocean
Bedroom
Exceptional
(41 reviews)

Affordable, oceanfront and walk to private beach gem

St. Thomas

8% off
NZ$4,703
for 7 nights, 1 apartment
NZ$672 per night
includes taxes & fees
Affordable, oceanfront and walk to private beach gem
Newly furnished and freshly painted studio right on the ocean.
View from patio never gets old...you hear the waves at all times.
Private kitchen
Swimming in the pool and listening to the waves...the perfect relaxing afternoon
Exceptional
(30 reviews)

CHECK OUT THE VIEW! Fantastic Affordable Oceanfront Studio - Listen to the Waves

St. Thomas

8% off
NZ$3,586
for 7 nights, 1 apartment
NZ$512 per night
includes taxes & fees
CHECK OUT THE VIEW! Fantastic Affordable Oceanfront Studio - Listen to the Waves
Room
Exterior
Interior
Interior
Exceptional
(19 reviews)

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

St. Thomas

7% off
NZ$2,300
for 7 nights, 1 apartment
NZ$329 per night
includes taxes & fees
Modern Cozy Studio 🎨 Shopping 🛍Historical 10 minute drive to 🏖
Dining
Pool
Private kitchen
Outdoor dining
Exceptional
(96 reviews)

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

St. Thomas

8% off
NZ$8,053
for 7 nights, 1 apartment
NZ$1,150 per night
includes taxes & fees
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
Living area
Outdoor dining
Property grounds
Interior
Exceptional
(5 reviews)

The Ampersand Garden Villa: Romantic, Artful Luxury

St. Thomas

13% off
NZ$6,182
for 7 nights, 1 villa
NZ$883 per night
includes taxes & fees
The Ampersand Garden Villa: Romantic, Artful Luxury
Living area
Exterior detail
Exceptional
(12 reviews)

Luxe Loft ❤️ of Downtown AC WiFi 5 minute 🚶🏽‍♀️to beautiful waterfront 🚤

St. Thomas

8% off
NZ$3,015
for 7 nights, 1 home
NZ$431 per night
includes taxes & fees
Luxe Loft ❤️ of Downtown AC WiFi 5 minute 🚶🏽‍♀️to beautiful waterfront 🚤
Bedroom
The Pool
Exterior
Gorgeous outdoor deck on the sand!
Exceptional
(13 reviews)

Sapphire Beach Resort Rental

St. Thomas

21% off
NZ$7,086
for 7 nights, 1 apartment
NZ$1,012 per night
includes taxes & fees
Sapphire Beach Resort Rental

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. 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)
  • Bolongo Bay (0.7 mi / 1.1 km)
  • Frenchman's Bay (1 mi / 1.5 km)
  • Morningstar Beach (1.4 mi / 2.2 km)
  • Wyndham Sugar Bay Beach (2.8 mi / 4.5 km)
  • Coki Point Beach (2.9 mi / 4.6 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, Bookabach 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 Bookabach 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 Bookabach 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, Bookabach 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 Bookabach.
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 Bookabach 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 Bookabach, 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 Bookabach holiday homes may also offer weekly or monthly discounted prices, so you can stick around for longer for less.