Southside Holiday Rentals

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Top Holiday Rentals Destinations in Southside

Marriott's Frenchman's Cove

4.0 star property
9.0 out of 10, Wonderful, (185)
"Loved our time at this property! Stunning views!"
The price is AU$1,084
includes taxes & fees
30 Aug - 31 Aug
Marriott's Frenchman's Cove

Hotel Sophia Boutique Hotel

4.0 star property
8.2 out of 10, Very good, (31)
" Beautiful views of the water. The room was clean, comfortable, and the host was great to deal with. "
The price is AU$604
includes taxes & fees
1 Sept - 2 Sept
Hotel Sophia Boutique Hotel

Pirates Pension at Bluebeard's Castle

3.0 star property
8.4 out of 10, Very good, (753)
"Safe and tranquil stay with a beautiful view of the port."
Pirates Pension at Bluebeard's Castle

Flamboyan on the Bay Resort and Villas

3.5 star property
8.6 out of 10, Excellent, (725)
"Great place to stay for Megan’s bay"
The price is AU$163
includes taxes & fees
7 Sept - 8 Sept
Flamboyan on the Bay Resort and Villas

Hilltop Villas at Bluebeard's Castle

3.0 star property
8.6 out of 10, Excellent, (1719)
"great place to stay"
Hilltop Villas at Bluebeard's Castle

Castle Villas at Bluebeard's

2.5 star property
8.6 out of 10, Excellent, (1179)
"Our stay at Bluebeards was phenomenal. The bar tenders were excellent. "
The price is AU$374
includes taxes & fees
3 Sept - 4 Sept
Castle Villas at Bluebeard's

Beachfront Villas at Crystal Cove

4.0 star property
9.6 out of 10, Exceptional, (135)
"The area was perfect as it’s close to red hook & the ferry to St. John, taxis everywhere to get wherever you need to go. "
Beachfront Villas at Crystal Cove

Sapphire Beach Resort

3.0 star property
6.8 out of 10, (267)
"It was close to the beach was a definite plus, only minus was having to leave. "
Sapphire Beach Resort

Gallows Point Resort

4.0 star property
9.6 out of 10, Exceptional, (528)
"Amazing accomodations!"
Gallows Point Resort

Sapphire Beach Villa

3.5 star property
9.4 out of 10, Exceptional, (65)
"Liked everything-villa, location, beach, pool, condition of community. "
Sapphire Beach Villa

Calichi at Picture Point

4.0 star property
9.8 out of 10, Exceptional, (72)
"Absolutely beautiful breathtaking view with beautiful sunrises. It was private and clean. I highly recommend this place. "
Calichi at Picture Point

Suite St. John at Gallows Point Resort

4.0 star property
8.6 out of 10, Excellent, (94)
"Amazing folks and space was beautiful..."
The price is AU$1,121
includes taxes & fees
30 Aug - 31 Aug
Suite St. John at Gallows Point Resort

ONE BEACH ROAD; 6 Bedroom, 5 1/2 Bath Beachfront Oasis St Thomas VI

10.0 out of 10, Exceptional, (118)
"We could not have asked for a more beautiful setting. "
ONE BEACH ROAD; 6 Bedroom, 5 1/2 Bath Beachfront Oasis St Thomas VI

Villa Marina Vista

4.0 star property
9.6 out of 10, Exceptional, (48)
"Great view. Accessible to ferries and restaurants. "
Villa Marina Vista

Virgin Islands Campground

2.0 star property
9.4 out of 10, Exceptional, (115)
"Excellent place to stay! "
Virgin Islands Campground

Blue Wrasse - Cute Little Cottage with Gorgeous Deck Views

9.8 out of 10, Exceptional, (179)
"Great views, wonderful natural setting sleeping with the trees!"
Blue Wrasse - Cute Little Cottage with Gorgeous Deck Views

“Secluded Romantic Villa with Private Pool—Nestled in Lush National Park Beauty”

9.8 out of 10, Exceptional, (94)
"It was clean and had an amazing view "
“Secluded Romantic Villa with Private Pool—Nestled in Lush National Park Beauty”

Celebrate time with friends & family! Private pool, float and take in the view!

9.6 out of 10, Exceptional, (173)
"Amazing views, pool was great and overall layout of house was excellent. The only reason it was not a 5 out 5 for us was the cleanliness of the kitchen. The bedrooms and bathrooms were clean. Emphasis on amaxing views. Simply stunning. The pictures of it on VRBO although beautiful do not do it justice."
Celebrate time with friends & family! Private pool, float and take in the view!

Sapphire Beach; St Thomas USVI; Sleep 4; STEPS FROM BEACH

10.0 out of 10, Exceptional, (61)
"The location was fantastic as it was just steps from the beach with restaurants on site. You could stay on property your entire visit and never need to leave. The unit also had a pool but we chose to spend all our time on the beautiful beach. The rental was very well furnished and had all the amenities you could need. We look forward to staying here again! "
Sapphire Beach; St Thomas USVI; Sleep 4; STEPS FROM BEACH

Crystal Shores Estate, Beautiful Island Estate Overlooking Fish Bay w/ Large Saltwater Pool

9.2 out of 10, Wonderful, (15)
"All in all our entire group was very satisfied and enjoyed this vacation Home. This location is great for large groups. The main kitchen and dining area were excellent with very nice views off of the attached decking. Our only complaint was with one bedroom in the lower level of the main house that obviously had a smoker that previously stayed there. We would definitely book this location again!"
Crystal Shores Estate, Beautiful Island Estate Overlooking Fish Bay w/ Large Saltwater Pool
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

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$163 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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia