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 beachfront hotel with multiple colorful buildings, a sandy beach, and rows of sun loungers with umbrellas.

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 NZ$1,061
includes taxes & fees
28 Sept - 29 Sept
Marriott's Frenchman's Cove
A bedroom with a bed, a nightstand, a lamp, and a view through a door.

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 NZ$710
includes taxes & fees
1 Oct - 2 Oct
Aqua
A room with two wicker chairs with blue cushions, a small table with a vase, and a door with a keyhole.

3. The Perch at Hawk Hill

The Perch at Hawk Hill
2.0 star property
St. Thomas
The price is NZ$566
includes taxes & fees
6 Oct - 7 Oct
The Perch at Hawk Hill
A coastal hotel with a beachfront view, a rocky shoreline, and a backdrop of hills.

4. NEW LISTING- Ideal Oceanside Location and Recent Renovation / DREAM Combination!

NEW LISTING- Ideal Oceanside Location and Recent Renovation / DREAM Combination!
St Thomas
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful ocean views with convenience of beach and restaurant access. Mike was fabulous to work with. He offers great tips and recommendations. "
United States
Susan R.
NEW LISTING- Ideal Oceanside Location and Recent Renovation / DREAM Combination!
A deck with a view of the ocean at dusk, featuring a palm tree, lounge chairs, and a railing.

5. 6 bedroom Villa and Pool side Villa with Private Pool, Sleeps 12

6 bedroom Villa and Pool side Villa with Private Pool, Sleeps 12
St Thomas
9.6 out of 10, Exceptional, (73 reviews)
"Wow, I was floored by my stay at the Frenchman's Villa. If this is available, jump on it, you won't regret it!The views, the pool, and all rooms are awesome. Victoria was an especially responsive host. We had a party of six staying and there was plenty of amenities for everyone. We cooked in one night and had all the comforts of home. "
United States
Andrew R.
The price is NZ$1,257
includes taxes & fees
28 Sept - 29 Sept
6 bedroom Villa and Pool side Villa with Private Pool, Sleeps 12
A tropical beach with clear turquoise water, rocky shoreline, and palm trees.

6. 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 NZ$1,032
includes taxes & fees
28 Sept - 29 Sept
Stunning St. Thomas Condo for Your Tropical Escape
A beach with clear water, palm trees, and distant hills.

7. 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 NZ$1,032
includes taxes & fees
28 Sept - 29 Sept
Discover Your Island Oasis: St. Thomas Condo
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 NZ$1,555
includes taxes & fees
28 Sept - 29 Sept
The Perch on Hawkhill, Lower Level
A spacious patio with a ceiling fan, wicker furniture, and a view of the ocean.

9. Charming, Hillside Villa with Ocean & Beach Views

Charming, Hillside Villa with Ocean & Beach Views
Southside
The price is NZ$1,190
includes taxes & fees
1 Oct - 2 Oct
Charming, Hillside Villa with Ocean & Beach Views
A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

10. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (861 reviews)
"Bluebeards is one of my favorite places to stay when I am on the island."
United States
Erica
The price is NZ$403
includes taxes & fees
26 Oct - 27 Oct
Bluebeard's Castle Resort
A clear turquoise sea with people swimming.

11. 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 NZ$503
includes taxes & fees
28 Sept - 29 Sept
Breathtaking Views from Sapphire Village II
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

12. 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, (254 reviews)
"Enjoyed our stay "
United States
Jason A.
The price is NZ$345
includes taxes & fees
29 Sept - 30 Sept
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
A beach with clear turquoise water, a sandy shore, and a distant island with buildings.

13. 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, (202 reviews)
"We LOVED our stay and would recommend it to anyone going to St. Thomas. The location was unbeatable, and the property was equipped with everything we needed and more!"
United States
Alessandra C.
The price is NZ$345
includes taxes & fees
29 Sept - 30 Sept
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

14. 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)
"Stayed for two and had a great time. Location was close to many tourist spots, hiking, shopping, and entertainments."
United States
Dede C.
The price is NZ$433
includes taxes & fees
28 Sept - 29 Sept
The Captain and the Mermaid - Adventures in Paradise are waiting!
An outdoor seating area with a pool view, covered by white canopies, and surrounded by potted plants.

15. Sophisticated Beach Condo-Ocean View-Sapphire

Sophisticated Beach Condo-Ocean View-Sapphire
Smith Bay
9.0 out of 10, Wonderful, (45 reviews)
"Clean room, AC worked great, pool is very close. Overall, a really cool place to stay."
United States
Michael
The price is NZ$504
includes taxes & fees
28 Sept - 29 Sept
Sophisticated Beach Condo-Ocean View-Sapphire
A living room with a sofa, chairs, a lamp, and a painting on the wall.

16. 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 NZ$649
includes taxes & fees
6 Oct - 7 Oct
The Landmark Apartment
A beach with clear turquoise water, sandy shore, and buildings in the background.

17. Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees

Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees
St. Thomas
9.8 out of 10, Exceptional, (142 reviews)
"We had an amazing stay, the condo was very clean and close to several beaches and restaurants."
United States
Jessica D.
The price is NZ$522
includes taxes & fees
28 Sept - 29 Sept
Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees
A beach with clear turquoise water, sandy shore, and buildings in the background.

18. Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307
St Thomas
9.8 out of 10, Exceptional, (128 reviews)
"Great place. I stay here two times a year. Always consistent. Always clean."
United States
John H.
The price is NZ$421
includes taxes & fees
28 Sept - 29 Sept
Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307
A beach with clear turquoise water and waves.

19. The Mermaid's Pearl at Sapphire Beach

The Mermaid's Pearl at Sapphire Beach
St. Thomas
9.8 out of 10, Exceptional, (164 reviews)
"The Mermaid’s Pearl was a comfortable fit for my son (19) and me. It is located in a quiet complex with a beautiful view from the balcony. The studio is a perfect size for two people and was very clean. We enjoyed the local restaurant (Sudi’s) and the pool just outside the front door, as well as the short walk to the Safire Beach complex (local coffee shop and eateries on the beach). We also walked into Red Hook which took about 20 minutes. Red Hook is small but has plenty of little shops and...
United States
Melissa
The price is NZ$471
includes taxes & fees
28 Sept - 29 Sept
The Mermaid's Pearl at Sapphire Beach
A living room with a sofa, a coffee table, a TV, and a view of the ocean through a sliding door.

20. Updated: Luxe Condo steps from Sapphire Beach!

Updated: Luxe Condo steps from Sapphire Beach!
St Thomas
9.8 out of 10, Exceptional, (98 reviews)
"Great stay, great place and great location"
United States
shane E.
The price is NZ$432
includes taxes & fees
12 Oct - 13 Oct
Updated: Luxe Condo steps from Sapphire Beach!
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

Buoy Haus Beach Resort St. Thomas, Autograph Collection

Buoy Haus Beach Resort St. Thomas, Autograph Collection

10/10 Excellent
"Karmissa and Armenia were"
Erica 4-night trip
Posted 2 days ago
Buoy Haus Beach Resort St. Thomas, Autograph Collection

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 favorite 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 NZ$1,061 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.