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Our top choices for Southside holiday rentals

Exterior
Marriott's Frenchman's Cove

Marriott's Frenchman's Cove

Marriott's Frenchman's Cove
4.0 star property
St. Thomas
9.0 out of 10, Wonderful, (187)
"the view was amazing… the room was perfect and very clean! Highly recommend! "
United States
Ron
The price is 26.814.985 ₫
30.166.990 ₫ total
includes taxes & fees
12 Jan - 13 Jan 2026
Marriott's Frenchman's Cove
View from property
Suite St. John at Gallows Point Resort

Suite St. John at Gallows Point Resort

Suite St. John at Gallows Point Resort
4.0 star property
St. John
8.6 out of 10, Excellent, (95)
"Amazing property and helpful staff. "
United States
Joseph
The price is 20.920.425 ₫
28.528.881 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Suite St. John at Gallows Point Resort
Terrace/patio
Shibui Cove

Shibui Cove

Shibui Cove
2.0 star property
St. Thomas
10.0 out of 10, Exceptional, (1)
"I had a great stay here. The view was absolutely stunning. Being up on the side of the mountain was great. Very private but less than 5 min away from town. I will definitely stay again. "
United States
Adam R
The price is 4.973.535 ₫
10.039.830 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Shibui Cove
Terrace/patio
Crystal Cove Beachfront Pool Tennis

Crystal Cove Beachfront Pool Tennis

Crystal Cove Beachfront Pool Tennis
3.0 star property
St. Thomas
8.0 out of 10, Very good, (12)
"Room was great. Beach was very good"
United States
Jeff
The price is 6.039.292 ₫
12.394.694 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Crystal Cove Beachfront Pool Tennis
Deluxe Apartment | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Villa Indigo 1BR in Private Gated Estate

Villa Indigo 1BR in Private Gated Estate

Villa Indigo 1BR in Private Gated Estate
3.5 star property
St. Thomas
9.0 out of 10, Wonderful, (26)
"It was great, clean apartment and definitely recommend going again or booking in the future."
United States
John
The price is 5.094.321 ₫
8.872.043 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Villa Indigo 1BR in Private Gated Estate
Aerial view
Beachfront Villas at Crystal Cove

Beachfront Villas at Crystal Cove

Beachfront Villas at Crystal Cove
4.0 star property
St. Thomas
9.6 out of 10, Exceptional, (150)
"Second time there. Just an over all beautiful property. "
United States
Erik
Beachfront Villas at Crystal Cove
Exterior
Villa Island Paradise

Villa Island Paradise

Villa Island Paradise
4.0 star property
St. John
9.2 out of 10, Wonderful, (7)
"Very safe and secure place! Also very clean! Just uphill from cruz bay "
United States
Tyler
The price is 3.407.818 ₫
18.796.795 ₫ total
includes taxes & fees
19 Jan - 20 Jan 2026
Villa Island Paradise
Terrace/patio
The Breeze St Thomas

The Breeze St Thomas

The Breeze St Thomas
2.0 star property
St. Thomas
The price is 7.631.350 ₫
13.295.655 ₫ total
includes taxes & fees
24 Dec - 25 Dec
The Breeze St Thomas
Interior
The Cottage at Villa Indigo

The Cottage at Villa Indigo

The Cottage at Villa Indigo
3.0 star property
St. Thomas
8.8 out of 10, Excellent, (15)
"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 6.844.531 ₫
11.673.925 ₫ total
includes taxes & fees
13 Jan - 14 Jan 2026
The Cottage at Villa Indigo
Cottage | 1 bedroom, iron/ironing board, free WiFi
Cottage at West 7 Palms

Cottage at West 7 Palms

Cottage at West 7 Palms
2.0 star property
St. Thomas
Cottage at West 7 Palms
Property entrance
The Landmark Apartment

The Landmark Apartment

The Landmark Apartment
2.5 star property
St. Thomas
8.8 out of 10, Excellent, (15)
"I loved the historic nature of the building. It had an interesting layout, but it was very spacious and clean, and had a wonderful location for walking around downtown and seeing the sights."
United States
Mercy
The price is 6.160.079 ₫
10.877.339 ₫ total
includes taxes & fees
23 Dec - 24 Dec
The Landmark Apartment
Deluxe Apartment, 1 Queen Bed with Sofa bed, Harbor View, Slope side, Apt#2 | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Little Indigo Apartments

Little Indigo Apartments

Little Indigo Apartments
3.5 star property
St. Thomas
8.4 out of 10, Very good, (22)
"Amazing views, very nice people"
United States
Ramie
The price is 5.068.269 ₫
8.840.130 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Little Indigo Apartments
Exterior
Bettyes Villa

Bettyes Villa

Bettyes Villa
4.0 star property
Charlotte Amalie
The price is 18.946.800 ₫
40.314.580 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Bettyes Villa
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

The Westin St. Thomas Beach Resort & Spa

The Westin St. Thomas Beach Resort & Spa

10/10 Excellent
"Was nervous to stay here after reading a sting of bad reviews and I must say my hotel stay blew me away!! Amazing ocean views from every angle of the hotel, delightful staff. "
Katherine 5-night trip
Posted 3 days ago
The Westin St. Thomas Beach Resort & Spa