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

Holiday Rentals in Southside

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Our top choices for Southside holiday rentals

A room with two wicker chairs with blue cushions, a small table with a vase, and a door with a keyhole.

1. The Perch at Hawk Hill

The Perch at Hawk Hill
2.0 star property
St. Thomas
The price is €307
includes taxes & fees
28 Oct - 29 Oct
The Perch at Hawk Hill
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 €359
includes taxes & fees
28 Oct - 29 Oct
Aqua
A beachfront hotel with multiple colorful buildings, a sandy beach, and rows of sun loungers with umbrellas.

3. 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 €662
includes taxes & fees
29 Oct - 30 Oct
Marriott's Frenchman's Cove
A balcony with wicker chairs and a small table overlooking a turquoise sea and green hills.

4. 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 €521
includes taxes & fees
27 Oct - 28 Oct
Stunning St. Thomas Condo for Your Tropical Escape
A coastal view with palm trees, a grassy area, and a rocky shoreline.

5. 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.
Discover Your Island Oasis: St. Thomas Condo
A balcony with a white railing, a blue sofa, and a hanging plant.

6. Private Terrace Suite with Ocean Views

Private Terrace Suite with Ocean Views
Southside
The price is €413
includes taxes & fees
20 Nov - 21 Nov
Private Terrace Suite with Ocean Views
A spacious patio with a ceiling fan, wicker furniture, and a view of the ocean.

7. Charming, Hillside Villa with Ocean & Beach Views

Charming, Hillside Villa with Ocean & Beach Views
Southside
The price is €648
includes taxes & fees
9 Nov - 10 Nov
Charming, Hillside Villa with Ocean & Beach Views
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 €809
includes taxes & fees
27 Oct - 28 Oct
The Perch on Hawkhill, Lower Level
A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

9. Bluebeard's Castle Resort

Bluebeard's Castle Resort
4.0 star property
Charlotte Amalie
9.0 out of 10, Wonderful, (920 reviews)
"Property was very clean and a beautiful place to stay."
United States
Freo
The price is €153
includes taxes & fees
24 Nov - 25 Nov
Bluebeard's Castle Resort
A coastal resort with beachfront villas, a golf course, and lush greenery.

10. 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, (258 reviews)
"We had an amazing time. It's highly recommended"
United States
Camierre
The price is €222
includes taxes & fees
6 Nov - 7 Nov
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!
A round wooden dining table set for six with wicker chairs, a vase of yellow flowers, and a hanging light fixture.

11. Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.6 out of 10, Exceptional, (41 reviews)
"View was amazing . Unit itself was very unique"
United States
Zach Ezekiel Azurus
The price is €503
includes taxes & fees
31 Oct - 1 Nov
Villa Island Paradise
A beachfront hotel with multiple buildings, a sandy beach, and rocky shoreline.

12. 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, (244 reviews)
"Great clean and safe place to stay"
United States
angela C.
The price is €219
includes taxes & fees
1 Nov - 2 Nov
The Captain and the Mermaid - Adventures in Paradise are waiting!
A swimming pool with lounge chairs and thatched umbrellas.

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, (203 reviews)
"Great place to stay and peaceful"
United States
Candice D.
The price is €222
includes taxes & fees
6 Nov - 7 Nov
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!
A modern kitchen with a marble countertop, bar seating, and a television.

14. 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
9.8 out of 10, Exceptional, (207 reviews)
"Greetings from St Thomas Capitol of the United States Virgin Islands. 90 Days Residency Required to become a United States Virgin Islands Citizen. USVI 5% IRS Corporate Tax rate on All World-Wide income without City or State Taxes just Open a Headquarters Expedia....."
United States
Kevin
The price is €238
includes taxes & fees
29 Oct - 30 Oct
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!
A covered outdoor seating area with wicker furniture, a bar, and a yellow building.

15. Octopus Den Glamping Site with AC

Octopus Den Glamping Site with AC
St John
10.0 out of 10, Exceptional, (8 reviews)
"Great for a short stay!"
United States
Kimberly J.
The price is €198
includes taxes & fees
30 Oct - 31 Oct
Octopus Den Glamping Site with AC
A poolside area with lounge chairs and tables, a pool, and surrounding greenery.

16. 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 €284
includes taxes & fees
27 Oct - 28 Oct
Breathtaking Views from Sapphire Village II
A bedroom with a bed, a desk, a chair, a ceiling fan, and a balcony with a view.

17. The Mermaid's Pearl at Sapphire Beach

The Mermaid's Pearl at Sapphire Beach
St. Thomas
9.8 out of 10, Exceptional, (164 reviews)
"Host was very courteous!! I will definitely be back!!"
United States
Tyneisha
The price is €239
includes taxes & fees
27 Oct - 28 Oct
The Mermaid's Pearl at Sapphire Beach
A wooden deck with lounge chairs and a pool, overlooking a body of water with boats and a mountainous backdrop.

18. Villa East - Panoramic waterfront view - Best location

Villa East - Panoramic waterfront view - Best location
6600 Estate Smith Bay, East End
9.6 out of 10, Exceptional, (52 reviews)
"Room was very clean and the staff at the resort were very helpful and friendly. The view was incredible!"
United States
Konner
Villa East - Panoramic waterfront view - Best location
A resort with a central pool, palm trees, and a view of the ocean.

19. 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, (510 reviews)
"Everything was amazing! It will always be my go to when I come to visit."
United States
Treacy
The price is €393
includes taxes & fees
11 Nov - 12 Nov
The Westin St. John Resort Villas
A balcony with a glass table and wicker chairs, overlooking a scenic landscape with hills and a body of water.

20. 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, (129 reviews)
"Super clean, hotness responsive. Would highly recommend"
United States
Nolan Y.
The price is €213
includes taxes & fees
27 Oct - 28 Oct
Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307
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

Hampton by Hilton St. Thomas

Hampton by Hilton St. Thomas

10/10 Excellent
"Loved the breakfast buffet! The staff was very helpful getting transportation our entire trip!"
Katie 4-night trip
Posted 3 days ago
Hampton by Hilton St. Thomas

Find out more about Southside

Holiday Homes in Southside

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