Southside Holiday Rentals

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Our top choices for Southside holiday rentals

Paradise near Limetree Beach

Paradise near Limetree Beach
St Thomas
9.6 out of 10, Exceptional, (13)
"This stay was very nice, the view was amazing,"
United States
Brandon r.
The price is AU$380
includes taxes & fees
9 Jan - 10 Jan
Paradise near Limetree Beach

Oceanfront Condo with Balcony, Pool & Fast Wi-Fi – Near Red Hook

Oceanfront Condo with Balcony, Pool & Fast Wi-Fi – Near Red Hook
St. Thomas
9.8 out of 10, Exceptional, (17)
"Great location and a very nice 1BR condo overlooking the ocean. We walked to nearby spots for food and drinks. Really liked this place and would stay again. "
United States
David
The price is AU$573
includes taxes & fees
15 Jan - 16 Jan
Oceanfront Condo with Balcony, Pool & Fast Wi-Fi – Near Red Hook

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
St. Thomas
10.0 out of 10, Exceptional, (84)
"The apartment was great. The view was amazing! Very comfortable. Would definitely stay again!!!"
United States
Dawn C.
The price is AU$997
includes taxes & fees
20 Jan - 21 Jan
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

Beautifully Renovated 3 Bedroom Home with 2 Bathrooms Centrally Located

Beautifully Renovated 3 Bedroom Home with 2 Bathrooms Centrally Located
St. Thomas
8.6 out of 10, Excellent, (11)
"The villa was perfect for my family and I. We had plenty of room. It was very convenient for us. We had doubts at first but once we entered the villa it was very nice. Thank you to Amanda and her team. We will be back to visit!!"
United States
Resa S.
The price is AU$1,014
includes taxes & fees
26 Jan - 27 Jan
Beautifully Renovated 3 Bedroom Home with 2 Bathrooms Centrally Located

Klarissa’s by The Sea by Villa Sunbeam.

Klarissa’s by The Sea by Villa Sunbeam.
st Thomas
The price is AU$783
includes taxes & fees
13 Jan - 14 Jan
Klarissa’s by The Sea by Villa Sunbeam.

Marriott's Frenchman's Cove

Marriott's Frenchman's Cove
4.0 star property
St. Thomas
9.0 out of 10, Wonderful, (189)
"the view was amazing… the room was perfect and very clean! Highly recommend! "
United States
Ron
The price is AU$1,702
includes taxes & fees
11 Jan - 12 Jan
Marriott's Frenchman's Cove

Lameshur Bay Glamping Site with AC

Lameshur Bay Glamping Site with AC
St John
10.0 out of 10, Exceptional, (25)
"The location is amazing, the space was clean, and the kitchen area, shower, and snorkeling/beach gear were much appreciated!"
United States
Ann
The price is AU$367
includes taxes & fees
12 Jan - 13 Jan
Lameshur Bay Glamping Site with AC

Salt Pond Bay Glamping Site With AC

Salt Pond Bay Glamping Site With AC
St John
The price is AU$369
includes taxes & fees
10 Jan - 11 Jan
Salt Pond Bay Glamping Site With AC

Family Glamping Site with AC

Family Glamping Site with AC
St John
10.0 out of 10, Exceptional, (32)
"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$476
includes taxes & fees
12 Jan - 13 Jan
Family Glamping Site with AC

Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (135)
"Absolutely would stay here again. We had zero issues with our stay. "
United States
Mark P.
The price is AU$656
includes taxes & fees
25 Jan - 26 Jan
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, (810)
"location nice pool "
United States
Gary
The price is AU$239
includes taxes & fees
9 Jan - 10 Jan
Flamboyan on the Bay Resort and Villas

Penthouse Views Full AC Coral Bay St John, Easy drive restaurants, bars, beaches

Penthouse Views Full AC Coral Bay St John, Easy drive restaurants, bars, beaches
St John
10.0 out of 10, Exceptional, (23)
"My husband and I stayed here shortly after getting married on Island. It was perfect for the two of us! Very clean, beautiful views and Sally’s directions were perfect. We have stayed on Coral Bay several times and this was one of our favorites! "
United States
Charity B.
The price is AU$939
includes taxes & fees
31 Jan - 1 Feb
Penthouse Views Full AC Coral Bay St John, Easy drive restaurants, bars, beaches

Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
8.0 out of 10, Very good, (11)
"We appreciated the beach chairs and cooler available for our use."
United States
Amber
The price is AU$1,072
includes taxes & fees
11 Jan - 12 Jan
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, (223)
"Clean, quiet, convenient location. Perfect stay!!!"
United States
Glenda
The price is AU$354
includes taxes & fees
31 Jan - 1 Feb
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

Colorful Caribbean Cottage • King Bed, Pool, Lush Garden Views

Colorful Caribbean Cottage • King Bed, Pool, Lush Garden Views
st. john
10.0 out of 10, Exceptional, (32)
"A great place for a weekend getaway"
United States
Gregory K.
The price is AU$984
includes taxes & fees
16 Jan - 17 Jan
Colorful Caribbean Cottage • King Bed, Pool, Lush Garden Views

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, (154)
"Condo was everything it was advertised to be - Sudi’s was the cherry on top"
United States
John A.
The price is AU$439
includes taxes & fees
20 Jan - 21 Jan
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

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, (180)
"This room was absolutely perfect for my stay in St Thomas. It had everything I needed and was convenient to all the places I had to visit during my stay. A short walk to the beach, plenty of very good on site restaurants, nice pools, incredible views every day. As far as the room the bed was comfortable. It had a nice big TV, small kitchen with big frig, blender and Pod Coffee maker. I liked that they even supplied snorkeling gear, coolers, beach chairs, sunscreen lotion, bug spray, aloe and...
United States
Paul
The price is AU$430
includes taxes & fees
1 Feb - 2 Feb
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

Lazy Loft: Tiny Room Loft Queen w Pool

Lazy Loft: Tiny Room Loft Queen w Pool
St. Thomas
10.0 out of 10, Exceptional, (11)
"Awesome Laid Back Island Asthethics"
United States
Ryan
The price is AU$271
includes taxes & fees
22 Jan - 23 Jan
Lazy Loft: Tiny Room Loft Queen w Pool

The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address

The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address
Maho Bay Quarter
9.6 out of 10, Exceptional, (27)
"Beautiful property with gorgeous views! Tommy was very quick to answer any questions or just give us information!"
United States
Amy G.
The price is AU$2,288
includes taxes & fees
7 Feb - 8 Feb
The Peter Bay 1BR Penthouse Suite at St John's Most Prestigious Address
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$239 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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