Southside Holiday Rentals from €346: Search Short-Term Rentals

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

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

1. Marriott's Frenchman's Cove

St. Thomas

Cathryn

includes taxes & fees

12 Sept - 13 Sept

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

2. The Perch at Hawk Hill

St. Thomas

includes taxes & fees

12 Sept - 13 Sept

A bedroom with a bed, a nightstand, a lamp, and a view through a door.

3. Aqua

St. Thomas

Paola

includes taxes & fees

1 Oct - 2 Oct

A tropical beach with clear turquoise water, rocky shoreline, and palm trees.

4. Stunning St. Thomas Condo for Your Tropical Escape

St. Thomas

Liz O.

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

St Thomas

Andrew R.

includes taxes & fees

24 Sept - 25 Sept

A beach with clear water, palm trees, and distant hills.

6. Discover Your Island Oasis: St. Thomas Condo

St. Thomas

Hope and J.

A balcony with a white railing, a blue sofa, and a hanging plant.

7. Private Terrace Suite with Ocean Views

Southside

A spacious patio with a ceiling fan, wicker furniture, and a view of the ocean.

8. Charming, Hillside Villa with Ocean & Beach Views

Southside

includes taxes & fees

1 Oct - 2 Oct

A balcony with a blue railing, two chairs with cushions, and a small table with a vase.

9. The Perch on Hawkhill, Lower Level

Saint Thomas

includes taxes & fees

24 Sept - 25 Sept

A restaurant with outdoor seating, palm trees, and a mountain in the background.

10. Octopus Den Glamping Site with AC

St John

Kimberly J.

includes taxes & fees

30 Sept - 1 Oct

A beach with turquoise water, sandy shore, and distant mountains.

11. Lameshur Cottage's Guest House

St John

Shawn C.

includes taxes & fees

12 Sept - 13 Sept

12. Turtle Nest Family Glamping Site with AC

St John

Carlee D.

includes taxes & fees

12 Sept - 13 Sept

13. Flamingo Grove Glamping Site with AC

St John

John

includes taxes & fees

12 Sept - 13 Sept

A balcony with a table, chairs, and a view of a turquoise sea and green hills.

14. Peter Bay Gatehouse

Maho Bay Quarter

Thomas

includes taxes & fees

19 Sept - 20 Sept

A beach with clear turquoise water, palm trees, and a distant island.

15. The Peter Bay 1BR Honeymoon Suite at St. John's Most Prestigious Address

Maho Bay Quarter

Tara C.

includes taxes & fees

11 Oct - 12 Oct

A resort with a central pool, palm trees, and a view of the ocean.

16. The Westin St. John Resort Villas

St. John

Rituparna

includes taxes & fees

24 Sept - 25 Sept

A coastal resort with multiple buildings, a swimming pool, and boats in the background.

17. Sunset Ridge Villas Unit D

St. John

Jessica

A wooden chair and table set against a lush green backdrop with a view of a valley and distant buildings.

18. Cozy Island Studio-5 Mins to Cruz Bay & Beaches

St John

Ashley

includes taxes & fees

12 Sept - 13 Sept

A tropical beach with clear turquoise waters, white sand, and lush greenery.

19. Villa Island Paradise

St. John

Angelo

includes taxes & fees

29 Sept - 30 Sept

A room with a hammock chair, a colorful door, and a wall-mounted sculpture.

20. St John Inn Boutique Hotel Suite w/ Kitchenette

Cruz Bay

Paul D.

includes taxes & fees

30 Sept - 1 Oct

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Top Southside Hotel Reviews

Buoy Haus Beach Resort St. Thomas, Autograph Collection

10/10 Excellent

"I loved the pool right on the beach. The food at all 3 restaurants was great. Staff was very friendly and helpful. Higher recommend staying here."

Bolongo Bay Beach Resort

10/10 Excellent

"This place is amazing and we will definitely be coming back!! It was the perfect Honeymoon Destination and lived up to the hype that is seen on TikTok and other social media platforms. The All Inclusive Option is truly All Inclusive, no extra fees, no hidden fees, and that makes it even more worth the trip to stay here. The staff is super friendly, helpful, and goes the extra mile. The food is amazing, every meal was delicious!! The chef’s are hilarious!! You can’t go wrong staying at Bolongo Bay!!!"

Limetree Beach Resort by Club Wyndham

8/10 Good

"We had a great time staying at the Limetree resort St. Thomas. The room was clean and as shown in the pictures. The pool, poolside bar, restaurant, outdoor areas were really nice. The beach right on the property is awesome (do recommend water shoes as it is rocky at most entries as others have mentioned). Great snorkeling to the left side near the rocks where the water remains a bit more calm. Highly recommend renting a car to get around the island (and to St. John via car ferry) if you stay here. I would give 5 stars all around but I will say in a 1 week stay there was no changing sheets or towels in the room. Not sure if this is something we were supposed to call for or not. Additionally when you check in they will likely try to get you to sign up for a timeshare presentation at the sister property (Margaritaville). JUST SAY NO IMMEDIATELY AND SHUT IT DOWN. We were pretty much hostage in the lobby for 30 minutes before they gave us our room key wristbands while trying desperately to get us to sign up for a meeting which we declined. On top of that, the associate lied to us about the price of parking at some of the beaches in attempt to scare us into going to the meeting so we could use their shuttle and parking service. (None of the beaches cost $50 to park which is just ridiculous). Anyway really enjoyed our stay and the location on island is phenomenal… just wish the staff were a little more attentive and it could have been 5 stars."

Gorgeous, Spa-like 3BR with Island Elegance & Stunning Ocean Views

10/10 Excellent

"I think this was our 2nd stay at CliffTop Villa and maybe 5th time staying at the Clifftop Apt! Every time has been STELLAR stay! Barb, the Host, is excellent in her communication, accessible and accommodating! Thanks Barb! The house and apartment have PERFECT views, were exceptionally clean and we found all that we needed for cooking meals, for movie night, for visiting the beaches and of course to relax! It was and always is the perfect stay! Can't wait til next year Barb!!! "

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."

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Holiday Homes 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. The Perch at Hawk Hill

3. Aqua

4. Stunning St. Thomas Condo for Your Tropical Escape

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

6. Discover Your Island Oasis: St. Thomas Condo

7. Private Terrace Suite with Ocean Views

8. Charming, Hillside Villa with Ocean & Beach Views

9. The Perch on Hawkhill, Lower Level

10. Octopus Den Glamping Site with AC

11. Lameshur Cottage's Guest House

12. Turtle Nest Family Glamping Site with AC

13. Flamingo Grove Glamping Site with AC

14. Peter Bay Gatehouse

15. The Peter Bay 1BR Honeymoon Suite at St. John's Most Prestigious Address

16. The Westin St. John Resort Villas

17. Sunset Ridge Villas Unit D

18. Cozy Island Studio-5 Mins to Cruz Bay & Beaches

19. Villa Island Paradise

20. St John Inn Boutique Hotel Suite w/ Kitchenette

Find holiday rentals that suit your style

Top Southside Hotel Reviews

Buoy Haus Beach Resort St. Thomas, Autograph Collection

Bolongo Bay Beach Resort

Hampton by Hilton St. Thomas

Limetree Beach Resort by Club Wyndham

Marriott's Frenchman's Cove

Oceanfront Villa-walk to resort-Generator & Solar

Gorgeous, Spa-like 3BR with Island Elegance & Stunning Ocean Views

Villa Mas: Also available as a 3 bedroom.

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

Find out more about Southside

Holiday Homes in Southside

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. The Perch at Hawk Hill

3. Aqua

4. Stunning St. Thomas Condo for Your Tropical Escape

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

6. Discover Your Island Oasis: St. Thomas Condo

7. Private Terrace Suite with Ocean Views

8. Charming, Hillside Villa with Ocean & Beach Views

9. The Perch on Hawkhill, Lower Level

10. Octopus Den Glamping Site with AC

11. Lameshur Cottage's Guest House

12. Turtle Nest Family Glamping Site with AC

13. Flamingo Grove Glamping Site with AC

14. Peter Bay Gatehouse

15. The Peter Bay 1BR Honeymoon Suite at St. John's Most Prestigious Address

16. The Westin St. John Resort Villas

17. Sunset Ridge Villas Unit D

18. Cozy Island Studio-5 Mins to Cruz Bay & Beaches

19. Villa Island Paradise

20. St John Inn Boutique Hotel Suite w/ Kitchenette

Find holiday rentals that suit your style

Top Southside Hotel Reviews

Buoy Haus Beach Resort St. Thomas, Autograph Collection

Find out more about Southside

Holiday Homes in Southside