Southside Holiday Rentals

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Our top choices for Southside holiday rentals

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, (19 reviews)
"Beautiful view, clean, kitchen utensils , pots and pans need a little replacing but I would stay here again in a second. Nice pool. Responsive owner."
United States
kenneth
The price is HK$1,240
HK$3,054 total
includes taxes & fees
4 Feb - 5 Feb
Oceanfront Condo with Balcony, Pool & Fast Wi-Fi – Near Red Hook

Eagles Nest Near the Beach

Eagles Nest Near the Beach
St Thomas
9.4 out of 10, Exceptional, (23 reviews)
"Great spot, great host. Albert was super helpful "
United States
McRae W.
The price is HK$807
HK$1,813 total
includes taxes & fees
27 Jan - 28 Jan
Eagles Nest Near the Beach

Paradise near Limetree Beach

Paradise near Limetree Beach
St Thomas
9.6 out of 10, Exceptional, (13 reviews)
"This stay was very nice, the view was amazing,"
United States
Brandon r.
The price is HK$982
HK$2,004 total
includes taxes & fees
25 Jan - 26 Jan
Paradise near Limetree Beach

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 reviews)
"The apartment was great. The view was amazing! Very comfortable. Would definitely stay again!!!"
United States
Dawn C.
The price is HK$2,070
HK$5,253 total
includes taxes & fees
20 Jan - 21 Jan
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa

Discover Your Island Oasis: St. Thomas Condo

Discover Your Island Oasis: St. Thomas Condo
St. Thomas
8.8 out of 10, Excellent, (9 reviews)
"Lovely property and excellent communication with the host - we would be delighted to return"
United States
Hope and J.
The price is HK$2,164
HK$5,757 total
includes taxes & fees
12 Feb - 13 Feb
Discover Your Island Oasis: St. Thomas Condo

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 reviews)
"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 HK$1,516
HK$5,387 total
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 HK$2,027
HK$4,156 total
includes taxes & fees
26 Jan - 27 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, (190 reviews)
"the view was amazing… the room was perfect and very clean! Highly recommend! "
United States
Ron
The price is HK$7,945
HK$8,938 total
includes taxes & fees
21 Jan - 22 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 reviews)
"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 HK$1,240
HK$2,104 total
includes taxes & fees
5 Feb - 6 Feb
Lameshur Bay Glamping Site with AC

Family Glamping Site with AC

Family Glamping Site with AC
St John
10.0 out of 10, Exceptional, (32 reviews)
"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 HK$1,630
HK$2,730 total
includes taxes & fees
20 Jan - 21 Jan
Family Glamping Site with AC

Salt Pond Bay Glamping Site With AC

Salt Pond Bay Glamping Site With AC
St John
The price is HK$1,116
HK$1,949 total
includes taxes & fees
20 Jan - 21 Jan
Salt Pond Bay Glamping Site With AC

Lameshur Cottage's Guest House

Lameshur Cottage's Guest House
St John
10.0 out of 10, Exceptional, (136 reviews)
"Absolutely would stay here again. We had zero issues with our stay. "
United States
Mark P.
The price is HK$1,860
HK$3,254 total
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, (817 reviews)
"location nice pool "
United States
Gary
The price is HK$1,116
HK$1,367 total
includes taxes & fees
7 Feb - 8 Feb
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 reviews)
"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 HK$2,842
HK$4,955 total
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 reviews)
"We appreciated the beach chairs and cooler available for our use."
United States
Amber
The price is HK$870
HK$5,261 total
includes taxes & fees
25 Jan - 26 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 reviews)
"Clean, quiet, convenient location. Perfect stay!!!"
United States
Glenda
The price is HK$546
HK$2,017 total
includes taxes & fees
1 Feb - 2 Feb
Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

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, (183 reviews)
"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 HK$546
HK$2,017 total
includes taxes & fees
1 Feb - 2 Feb
Renovated/new condo-Walk to Beach, Marina, Pools. Red Hook, Ferry, Bars near by!

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, (155 reviews)
"Condo was everything it was advertised to be - Sudi’s was the cherry on top"
United States
John A.
The price is HK$468
HK$2,140 total
includes taxes & fees
20 Jan - 21 Jan
Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

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
9.6 out of 10, Exceptional, (119 reviews)
"Arrived to find a clean unit with an astonishing view. Proximity to Sapphire Beach and nearby dining was very convenient, and grocery stores and the St John ferry were close enough for affordable taxi trips. "
United States
Trevor
The price is HK$1,115
HK$2,307 total
includes taxes & fees
27 Jan - 28 Jan
Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

Peter Bay Gatehouse

Peter Bay Gatehouse
4.0 star property
Maho Bay Quarter
8.4 out of 10, Very good, (19 reviews)
"Staying at the gate house was wonderful. Walk to beach was a little longer than expected because of the sharp incline. Very nice place to stay!! "
United States
jonathan
The price is HK$6,978
HK$9,559 total
includes taxes & fees
26 Jan - 27 Jan
Peter Bay Gatehouse
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