A marina with numerous sailboats and yachts docked, surrounded by a coastal town and lush green hills.

Southside Holiday Rentals

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Our top choices for Southside holiday rentals

A room with two wicker chairs with blue cushions, a small table with a vase, and a door with a keyhole.

1. The Perch at Hawk Hill

The Perch at Hawk Hill
2.0 star property
St. Thomas
The price is AU$495
includes taxes & fees
18 Oct - 19 Oct
The Perch at Hawk Hill
A beachfront hotel with multiple colorful buildings, a sandy beach, and rows of sun loungers with umbrellas.

2. Marriott's Frenchman's Cove

Marriott's Frenchman's Cove
4.0 star property
St. Thomas
9.0 out of 10, Wonderful, (207 reviews)
"The property is well maintained and comfortable. Our family enjoyed the private beach and the pool. The one on-site restaurant serves a variety of good food."
United States
Cathryn
The price is AU$1,019
includes taxes & fees
22 Oct - 23 Oct
Marriott's Frenchman's Cove
A bedroom with a bed, a nightstand, a lamp, and a view through a door.

3. Aqua

Aqua
3.0 star property
St. Thomas
9.4 out of 10, Exceptional, (8 reviews)
"Comfortable and beautiful area"
United States
Paola
The price is AU$547
includes taxes & fees
30 Oct - 31 Oct
Aqua
A beach with clear water, palm trees, and distant hills.

4. Discover Your Island Oasis: St. Thomas Condo

Discover Your Island Oasis: St. Thomas Condo
St. Thomas
8.8 out of 10, Excellent, (10 reviews)
"Lovely property and excellent communication with the host - we would be delighted to return"
United States
Hope and J.
The price is AU$820
includes taxes & fees
18 Oct - 19 Oct
Discover Your Island Oasis: St. Thomas Condo
A tropical beach with clear turquoise water, rocky shoreline, and palm trees.

5. Stunning St. Thomas Condo for Your Tropical Escape

Stunning St. Thomas Condo for Your Tropical Escape
St. Thomas
9.6 out of 10, Exceptional, (34 reviews)
"Very clean and easy to navigate. Beds were comfortable and the unit was quiet. Gorgeous view. Nice to be next to iggys and the bolongo restaurant"
United States
Kelly
The price is AU$820
includes taxes & fees
19 Oct - 20 Oct
Stunning St. Thomas Condo for Your Tropical Escape
A balcony with a white railing, a blue sofa, and a hanging plant.

6. Private Terrace Suite with Ocean Views

Private Terrace Suite with Ocean Views
Southside
Private Terrace Suite with Ocean Views
A spacious patio with a ceiling fan, wicker furniture, and a view of the ocean.

7. Charming, Hillside Villa with Ocean & Beach Views

Charming, Hillside Villa with Ocean & Beach Views
Southside
The price is AU$929
includes taxes & fees
23 Oct - 24 Oct
Charming, Hillside Villa with Ocean & Beach Views
A balcony with a blue railing, two chairs with cushions, and a small table with a vase.

8. The Perch on Hawkhill, Lower Level

The Perch on Hawkhill, Lower Level
Saint Thomas
The price is AU$1,252
includes taxes & fees
18 Oct - 19 Oct
The Perch on Hawkhill, Lower Level
A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

9. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (900 reviews)
"Property was very clean and a beautiful place to stay."
United States
Freo
The price is AU$293
includes taxes & fees
17 Nov - 18 Nov
Bluebeard's Castle Resort
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

10. Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
St. Thomas
9.4 out of 10, Exceptional, (258 reviews)
"We had an amazing time. It's highly recommended"
United States
Camierre
The price is AU$317
includes taxes & fees
23 Oct - 24 Oct
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
A coastal landscape with a beach, clear blue waters, and lush greenery.

11. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (41 reviews)
"View was amazing . Unit itself was very unique"
United States
Zach Ezekiel Azurus
The price is AU$704
includes taxes & fees
20 Oct - 21 Oct
Villa Island Paradise
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

12. The Captain and the Mermaid - Adventures in Paradise are waiting!

The Captain and the Mermaid - Adventures in Paradise are waiting!
St Thomas
9.8 out of 10, Exceptional, (243 reviews)
"Great clean and safe place to stay"
United States
angela C.
The price is AU$346
includes taxes & fees
20 Oct - 21 Oct
The Captain and the Mermaid - Adventures in Paradise are waiting!
A beach with clear turquoise water and waves.

13. The Mermaid's Pearl at Sapphire Beach

The Mermaid's Pearl at Sapphire Beach
St. Thomas
9.8 out of 10, Exceptional, (164 reviews)
"Host was very courteous!! I will definitely be back!!"
United States
Tyneisha
The price is AU$370
includes taxes & fees
18 Oct - 19 Oct
The Mermaid's Pearl at Sapphire Beach
A clear turquoise sea with people swimming.

14. Breathtaking Views from Sapphire Village II

Breathtaking Views from Sapphire Village II
St Thomas
8.8 out of 10, Excellent, (40 reviews)
"The room was beautiful great View locations on point for everything you needed within the area the only downfall I would say was the hill if you're walking and if you have any type of handicap but other than that beautiful place to stay"
United States
Jason
The price is AU$439
includes taxes & fees
24 Oct - 25 Oct
Breathtaking Views from Sapphire Village II
A beach with clear turquoise water, a sandy shore, and a distant island with buildings.

15. Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
St. Thomas
9.6 out of 10, Exceptional, (203 reviews)
"Great place to stay and peaceful"
United States
Candice D.
The price is AU$320
includes taxes & fees
18 Oct - 19 Oct
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
A beach with clear turquoise water, gentle waves, and distant islands.

16. 1BR Oceanfront Sapphire Beach, LOCATION, LOCATION, B-106 Beach level

1BR Oceanfront Sapphire Beach, LOCATION, LOCATION, B-106 Beach level
St Thomas
9.8 out of 10, Exceptional, (160 reviews)
"Perfect room for our vacation! Close enough to the sapphire beach restaurant and pool but far enough away to still be quiet at night. "
United States
Michelle M.
The price is AU$736
includes taxes & fees
31 Oct - 1 Nov
1BR Oceanfront Sapphire Beach, LOCATION, LOCATION, B-106 Beach level
A resort with a central pool, palm trees, and a view of the ocean.

17. The Westin St. John Resort Villas

The Westin St. John Resort Villas
4.5 star property
St. John
8.4 out of 10, Very good, (509 reviews)
"Everything was amazing! It will always be my go to when I come to visit."
United States
Treacy
The price is AU$568
includes taxes & fees
1 Nov - 2 Nov
The Westin St. John Resort Villas
A spacious living area with a sofa, dining table, and chairs, overlooking a scenic ocean view.

18. The Breeze

The Breeze
2.0 star property
ST Thomas
The price is AU$1,221
includes taxes & fees
18 Oct - 19 Oct
The Breeze
A beach with clear turquoise water, rocky shore, and a wooden walkway leading to beach chairs.

19. Villa East - Panoramic waterfront view - Best location

Villa East - Panoramic waterfront view - Best location
6600 Estate Smith Bay, East End
9.6 out of 10, Exceptional, (52 reviews)
"Room was very clean and the staff at the resort were very helpful and friendly. The view was incredible!"
United States
Konner
Villa East - Panoramic waterfront view - Best location
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

20. Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
St Thomas
9.6 out of 10, Exceptional, (174 reviews)
"Excellent location and very nice place to visit and Sudi's Bar/restaurant is the place to be and the whole staff is Excellent and the food is delicious and reminds you of Cheers 😎."
United States
Quincy
The price is AU$408
includes taxes & fees
19 Oct - 20 Oct
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southside Hotel Reviews

The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

8/10 Good
"We had a wonderful stay at The Westin St. Thomas! Beautiful ocean views, a relaxing atmosphere, and an overall amazing experience. The perfect getaway!"
Harry 4-night trip
Posted 22 hours ago
The Westin St. Thomas Beach Resort & Spa

Find out more about Southside

Everything you need to know about Southside holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southside holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southside holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Southside holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southside. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southside holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Southside holiday rentals we have chosen for you start as low as AU$547 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Southside rentals

At Expedia, we put the best Southside holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southside holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.