Southside Holiday Rentals

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Our top choices for Southside holiday rentals

Regatta’s Island Time Getaway

Regatta’s Island Time Getaway
St Thomas
9.2 out of 10, Wonderful, (13 reviews)
"Perfect for a couple. Has everything you need for a comfortable stay. Quiet in the evenings for good nights sleep. Looking forward to returning. "
United States
Frank
The price is AU$504
includes taxes & fees
24 Apr - 25 Apr
Regatta’s Island Time Getaway

Aqua

Aqua
3.0 star property
St. Thomas
9.8 out of 10, Exceptional, (6 reviews)
"Comfortable and beautiful area"
United States
Paola
The price is AU$535
includes taxes & fees
22 Apr - 23 Apr
Aqua

1 bed, 1 bath, Ocean views, 3 Pools, Walk to Beach

1 bed, 1 bath, Ocean views, 3 Pools, Walk to Beach
St. Thomas
The price is AU$1,035
includes taxes & fees
14 Apr - 15 Apr
1 bed, 1 bath, Ocean views, 3 Pools, Walk to Beach

Generator! 4BR remodeled, w/BEACH and 3 POOLS!

Generator! 4BR remodeled, w/BEACH and 3 POOLS!
St. Thomas
10.0 out of 10, Exceptional, (14 reviews)
"The view was so beautiful, you can see the bay along with the land/mountains and the beach! The property is right next to the beach entrance (so convenient!!) along with a couple of great restaurants. The place was clean on arrival and the hosts were responsive. Overall, a GREAT place to stay—my family and I loved it!!"
United States
Nandini R.
Generator! 4BR remodeled, w/BEACH and 3 POOLS!

FABULOUS! So close you can taste the ocean - Amazing NEWLY RENOVATED condo !

FABULOUS! So close you can taste the ocean - Amazing NEWLY RENOVATED condo !
St Thomas
10.0 out of 10, Exceptional, (23 reviews)
"Was a super relaxing atmosphere! Great place to unwind .an"
United States
Alicia L.
The price is AU$1,396
includes taxes & fees
4 May - 5 May
FABULOUS! So close you can taste the ocean - Amazing NEWLY RENOVATED condo !

The Perch at Hawkhill, Lower Level

The Perch at Hawkhill, Lower Level
Saint Thomas
The price is AU$780
includes taxes & fees
9 Apr - 10 Apr
The Perch at Hawkhill, Lower Level

Marriott's Frenchman's Cove

Marriott's Frenchman's Cove
4.0 star property
St. Thomas
9.0 out of 10, Wonderful, (196 reviews)
"Beautiful pool and beach. Great view from the villa. "
United States
Daniel
The price is AU$1,371
includes taxes & fees
4 May - 5 May
Marriott's Frenchman's Cove

Oceanview 2BR Villa | Marriott Frenchman's Cove

Oceanview 2BR Villa | Marriott Frenchman's Cove
Charlotte Amalie
The price is AU$1,651
includes taxes & fees
7 May - 8 May
Oceanview 2BR Villa | Marriott Frenchman's Cove

Family Glamping Site with AC

Family Glamping Site with AC
St John
10.0 out of 10, Exceptional, (33 reviews)
"Thoughtful to have bug swatters, dart boards, honor system drinks/snacks, sunscreen/bug spray. Couches/chairs/hammocks decks were great and Frisbee golf hole/discs!"
United States
Kelly
The price is AU$490
includes taxes & fees
1 May - 2 May
Family Glamping Site with AC

Salt Pond Bay Glamping Site With AC

Salt Pond Bay Glamping Site With AC
St John
10.0 out of 10, Exceptional, (5 reviews)
"Very clean"
United States
James
The price is AU$350
includes taxes & fees
16 Apr - 17 Apr
Salt Pond Bay Glamping Site With AC

Lameshur Bay Glamping Site with AC

Lameshur Bay Glamping Site with AC
St John
10.0 out of 10, Exceptional, (29 reviews)
"Really enjoyed our stay. We felt well taken care of and loved the location!"
United States
John
The price is AU$357
includes taxes & fees
13 Apr - 14 Apr
Lameshur Bay Glamping Site with AC

Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (140 reviews)
"Best place for a vacation, great view from the cottage.Great host and thank you very much Bill for the Christmas gift."
United States
Suresh Kumar B.
The price is AU$592
includes taxes & fees
1 May - 2 May
Lameshur Cottage's Guest House

Flamboyan on the Bay Resort and Villas

Flamboyan on the Bay Resort and Villas
3.5 star property
St. Thomas
8.6 out of 10, Excellent, (854 reviews)
"Excellent stay resort was perfectly located "
United States
andrew
The price is AU$171
includes taxes & fees
7 May - 8 May
Flamboyan on the Bay Resort and Villas

Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
8.8 out of 10, Excellent, (22 reviews)
"Everything was clean and well appointed."
United States
Josh
The price is AU$990
includes taxes & fees
29 Apr - 30 Apr
Villa Island Paradise

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, (236 reviews)
"The place was spotless "
United States
Harvey A
The price is AU$314
includes taxes & fees
12 Apr - 13 Apr
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

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, (165 reviews)
"Great location"
United States
Aleric
The price is AU$402
includes taxes & fees
19 Apr - 20 Apr
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire
Smith Bay
9.0 out of 10, Wonderful, (38 reviews)
"Clean, comfortable and conveniently located to beach, ferry and restaurants."
United States
Deborah
The price is AU$398
includes taxes & fees
5 May - 6 May
Sophisticated Beach Condo-Ocean View-Sapphire

Studio Double @ WorldMark Elysian Beach Resort

Studio Double @ WorldMark Elysian Beach Resort
St Thomas
9.6 out of 10, Exceptional, (4 reviews)
"Facilities were nice and check in easy. We enjoyed our stay."
United States
Joe L.
The price is AU$663
includes taxes & fees
15 Apr - 16 Apr
Studio Double @ WorldMark Elysian Beach Resort

On the Beach! 1 Min Walk to Dining - STJ Ferry

On the Beach! 1 Min Walk to Dining - STJ Ferry
St. Thomas
10.0 out of 10, Exceptional, (26 reviews)
"Excellent place. Great restaurant and bar right next door!"
United States
Darryl
On the Beach! 1 Min Walk to Dining - STJ Ferry

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, (187 reviews)
"Very nice condo"
United States
Janice B.
The price is AU$317
includes taxes & fees
17 Apr - 18 Apr
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, 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

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$171 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. 

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