Holiday Rentals Southside from £184: Find Short-Term Rentals & Holiday Accommodations

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

St. Thomas

Cathryn

includes taxes & fees

22 Aug - 23 Aug

Luxury Apartment, 1 Bedroom, Sea Facing | 1 bedroom, Egyptian cotton sheets, premium bedding, down duvets

2. Aqua

St. Thomas

Paola

includes taxes & fees

13 Aug - 14 Aug

Family Apartment, Ocean View | Terrace/patio

3. The Perch at Hawk Hill

St. Thomas

includes taxes & fees

13 Aug - 14 Aug

4. Bluebeard's Castle Resort

Charlotte Amalie

Janice

includes taxes & fees

10 Sept - 11 Sept

5. Villa Island Paradise

St. John

Quoc Phong Eric

includes taxes & fees

16 Aug - 17 Aug

Outdoor pool, pool cabanas (surcharge), pool loungers

6. The Westin St. John Resort Villas

St. John

Rituparna

includes taxes & fees

1 Sept - 2 Sept

City Apartment, 3 Bedrooms, Kitchen, City View | Living room | 45-inch TV with digital channels, Netflix, Hulu

7. The Landmark Apartment

St. Thomas

Eileen

includes taxes & fees

14 Aug - 15 Aug

8. Shibui Cove

St. Thomas

William Eric

includes taxes & fees

22 Aug - 23 Aug

Luxury Suite Ocean View Upper 15D | View from room

9. Suite St. John at Gallows Point Resort

St. John

Sean

includes taxes & fees

13 Aug - 14 Aug

10. Villa Indigo 1BR in Private Gated Estate

St. Thomas

Trent

includes taxes & fees

22 Aug - 23 Aug

Panoramic Apartment, 2 Bedrooms, Harbor View, Sea Facing, Apt#3 | Terrace/patio

11. Little Indigo Apartments

St. Thomas

Lynda

includes taxes & fees

13 Aug - 14 Aug

Cottage | 2 bedrooms, premium bedding, down duvets, pillow-top beds

12. The Cottage at Villa Indigo

St. Thomas

Oronde

includes taxes & fees

13 Aug - 14 Aug

13. The Breeze

ST Thomas

includes taxes & fees

18 Aug - 19 Aug

14. Peter Bay Gatehouse

Maho Bay Quarter

Thomas

includes taxes & fees

13 Aug - 14 Aug

15. Sunset Ridge Villas Unit D

St. John

Jessica

includes taxes & fees

5 Sept - 6 Sept

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

St. Thomas

includes taxes & fees

16 Aug - 17 Aug

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Top Southside Hotel Reviews

Hampton by Hilton St. Thomas

10/10 Excellent

"I absolutely loved my stay at the Hampton by Hilton in St.Thomas. The staff was INCREDIBLY helpful with EVERYTHING and oh so kind. Front desk Deva and Icesha (maybe misspelled) went above and beyond to be kind and welcoming. The place is SPOTLESS! They’re constantly cleaning and each time you walk in there is this pleasant smell that drifts towards you. The breakfast is actually good (hot waffles!) and it’s always stocked and area kept clean. We were on the first floor right outside by the pool where the cruise ships docked (although only one came) and had great access to everything. The outside veranda area where the bar is , is great with a spectacular view and again very well kept and clean . I highly recommend Hampton Inn as it is a great , good value stay"

Limetree Beach Resort by Club Wyndham

10/10 Excellent

"The room was nice and clean, loved the property, they do use golf carts to pick you up from the room. loved how the beach was so close by. Had an electricity problem in the room which was resolved in about 20 minutes. Was reeled into a timeshare meeting but nothing we haven’t done already and it cane with some perks afterwards so if you have the time on vacation but can easily be skipped by telling them you are not interested"

Very Romantic Secluded Beach Getaway in St. Thomas Island

8/10 Good

"Everyone was so nice! The check in process was easy and the concierge gave us some great recommendations. The rooms were super clean and came with plenty of shampoo and conditioner which is a plus for me! The beach view from our room was amazing and the terrace was incredibly clean."

3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor

10/10 Excellent

"Pictures do not do this villa justice. It is even more impressive in person. The cleanest and most equipped rental we have ever stayed in to date. Excellent communication from Tony and Leah answered our every question quickly and thoroughly. We spent a ton of time enjoying the outside deck and pool. It was so quiet and peaceful at all times of the day. We would definitely book again without hesitation."

Oceanfront Villa-walk to resort-Generator & Solar

10/10 Excellent

"Absolutely loved our stay at Frenchman’s Breeze. The minute we walked in I could feel myself relax. The view is incredible and you can’t beat the waking up and falling asleep to the sounds of the waves. Snorkeling right off the beach was great! The driveway is a little daunting at first but you do get used to it. Tressa was extremely responsive and helpful with local recommendations. We would definitely stay here again!"

Very Romantic Secluded Beach Getaway in St. Thomas Island

10/10 Excellent

"Great pool with iguanas. Each room had an outdoor seating space. There are a lot of steps up to rooms, so if you can't do them you may want to ask about ground floor. Our studio had a full kitchenette with dishes etc. There was a great Market on-site with sandwiches, beer,wine,snacks and eggs, milk etc. The restaurant Longboards was amazing and pool bar was great. Overall, wonderful experience"

Private Paradise! One level, panoramic views from every room!

10/10 Excellent

"Dream vacation of a life-time! The property is as described, and then some. The home was spotless! The pool to die for! The view - majestic! Our hosts - perfect!Our family of six adults thoroughly enjoyed our 7-day stay. Weather was perfect and there are many things to do in Charlotte Amalie. There were many amenities that were very much appreciated (i.e. beach towels & chairs, coffee pot, a good selection of pots and pans, cutlery, dishes, and plenty of kitchen towels. There is a washer/dryer for use, an office area if you need one. All bedrooms are king beds with separate air-conditioning units, that kept us cool during the night. Each bedroom had a large slider to the porch with a view to die for. We could see the cruise ships coming and going and the evening lights from our porch were beautiful.We enjoyed one special dinner night where we hired a private chef [Ultimate Chefs] that was one of the listed recommendations from our hosts. This dinner was the highlight of our stay. LeAnne and Beige from Ultimate Chefs were engaging and very professional and the dinner was awesome! If you have the opportunity to enjoy this villa, I would highly recommend it. Our hosts, Melissa and Juanda were responsive and very friendly and accommodating. There is a notebook full of great information and helpful suggestions. Go! Do It!"

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Holiday Apartments in Southside

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Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Southside holiday rentals

1. Marriott's Frenchman's Cove

2. Aqua

3. The Perch at Hawk Hill

4. Bluebeard's Castle Resort

5. Villa Island Paradise

6. The Westin St. John Resort Villas

7. The Landmark Apartment

8. Shibui Cove

9. Suite St. John at Gallows Point Resort

10. Villa Indigo 1BR in Private Gated Estate

11. Little Indigo Apartments

12. The Cottage at Villa Indigo

13. The Breeze

14. Peter Bay Gatehouse

15. Sunset Ridge Villas Unit D

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

Find holiday rentals that suit your style

Top Southside Hotel Reviews

Hampton by Hilton St. Thomas

Buoy Haus Beach Resort St. Thomas, Autograph Collection

Villa Mas: Also available as a 3 bedroom.

Limetree Beach Resort by Club Wyndham

Very Romantic Secluded Beach Getaway in St. Thomas Island

3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor

Oceanfront Villa-walk to resort-Generator & Solar

Very Romantic Secluded Beach Getaway in St. Thomas Island

Private Paradise! One level, panoramic views from every room!

Find out more about Southside

Holiday Apartments in Southside

Explore a world of travel with Expedia

Search Holiday Rentals in Southside

Change your mind

Treat yourself

Be picky

Our top choices for Southside holiday rentals

1. Marriott's Frenchman's Cove

2. Aqua

3. The Perch at Hawk Hill

4. Bluebeard's Castle Resort

5. Villa Island Paradise

6. The Westin St. John Resort Villas

7. The Landmark Apartment

8. Shibui Cove

9. Suite St. John at Gallows Point Resort

10. Villa Indigo 1BR in Private Gated Estate

11. Little Indigo Apartments

12. The Cottage at Villa Indigo

13. The Breeze

14. Peter Bay Gatehouse

15. Sunset Ridge Villas Unit D

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

Find holiday rentals that suit your style

Top Southside Hotel Reviews

Hampton by Hilton St. Thomas

Find out more about Southside

Holiday Apartments in Southside

Explore a world of travel with Expedia