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

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Our top choices for Southside holiday rentals

1. 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 £679
includes taxes & fees
12 Dec - 13 Dec
Marriott's Frenchman's Cove

2. 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 £302
includes taxes & fees
15 Dec - 16 Dec
Aqua

3. The Perch at Hawk Hill

The Perch at Hawk Hill
2.0 star property
St. Thomas
The price is £260
includes taxes & fees
16 Nov - 17 Nov
The Perch at Hawk Hill

4. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (973 reviews)
"Enjoyed my stay"
United States
James Theodore
The price is £136
includes taxes & fees
16 Nov - 17 Nov
Bluebeard's Castle Resort

5. Suite St. John at Gallows Point Resort

Suite St. John at Gallows Point Resort
4.0 star property
St. John
8.8 out of 10, Excellent, (106 reviews)
"Friendly staff. Beautiful property."
United States
Sean
The price is £689
includes taxes & fees
15 Nov - 16 Nov
Suite St. John at Gallows Point Resort

6. 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, (517 reviews)
"The ferry that the Westin provides was awesome. Everyone was very friendly"
United States
Jean
The price is £312
includes taxes & fees
28 Nov - 29 Nov
The Westin St. John Resort Villas

7. Beachfront Villas at Crystal Cove

Beachfront Villas at Crystal Cove
4.0 star property
St. Thomas
9.6 out of 10, Exceptional, (179 reviews)
"We had great 8 days at this property. We are so happy with our stay. We got everything we need for wonderful vacation. Location is excellent, villa very clean and staffed with everything and has a lot of extras."
United States
Olena
The price is £383
includes taxes & fees
25 Nov - 26 Nov
Beachfront Villas at Crystal Cove

8. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (42 reviews)
"View was amazing . Unit itself was very unique"
United States
Zach Ezekiel Azurus
The price is £413
includes taxes & fees
18 Nov - 19 Nov
Villa Island Paradise

9. The Breeze

The Breeze
2.0 star property
ST Thomas
The price is £143
includes taxes & fees
23 Nov - 24 Nov
The Breeze

10. Villa Indigo 1BR in Private Gated Estate

Villa Indigo 1BR in Private Gated Estate
3.5 star property
St. Thomas
8.8 out of 10, Excellent, (33 reviews)
"Excellent place"
United States
Trent
The price is £243
includes taxes & fees
15 Nov - 16 Nov
Villa Indigo 1BR in Private Gated Estate

11. The Landmark Apartment

The Landmark Apartment
2.5 star property
St. Thomas
8.6 out of 10, Excellent, (18 reviews)
"Wonderful place to stay and Ali the cab driver was also amazing "
United States
Eileen
The price is £324
includes taxes & fees
15 Dec - 16 Dec
The Landmark Apartment

12. The Cottage at Villa Indigo

The Cottage at Villa Indigo
3.0 star property
St. Thomas
8.8 out of 10, Excellent, (15 reviews)
"We got a true dose of the life experience on the island staying here. The entire experience was MAGICAL!!!! Me and my family will most definitely staying again when we come back "
United States
Oronde
The price is £338
includes taxes & fees
27 Nov - 28 Nov
The Cottage at Villa Indigo

13. Peter Bay Gatehouse

Peter Bay Gatehouse
4.0 star property
Maho Bay Quarter
8.2 out of 10, Very good, (21 reviews)
"Outstanding view from the villa"
United States
Thomas
The price is £793
includes taxes & fees
15 Nov - 16 Nov
Peter Bay Gatehouse

14. Little Indigo Apartments

Little Indigo Apartments
3.5 star property
St. Thomas
7.8 out of 10, Good, (30 reviews)
"The apartment had an amazing view. It was clean and well prepared prior to our arrival. I look forward to our next visit."
United States
Lynda
The price is £273
includes taxes & fees
4 Dec - 5 Dec
Little Indigo Apartments

15. St Thomas Cliffside Villa With Pool & Hot Tub!

St Thomas Cliffside Villa With Pool & Hot Tub!
3.5 star property
St. Thomas
The price is £856
includes taxes & fees
18 Nov - 19 Nov
St Thomas Cliffside Villa With Pool & Hot Tub!
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, apart-hotels, 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 depends 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 selected for you start as low as £302 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.