Southside Vacation Rentals from ￥94,487: 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 vacation 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

￥94,487 total

includes taxes & fees

Sep 28 - Sep 29

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

￥54,049 total

includes taxes & fees

Sep 28 - Sep 29

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

3. Aqua

St. Thomas

Paola

￥63,829 total

includes taxes & fees

Oct 1 - Oct 2

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

4. Stunning St. Thomas Condo for Your Tropical Escape

St. Thomas

Kelly

￥92,918 total

includes taxes & fees

Sep 27 - Sep 28

A deck with a view of the ocean at dusk, featuring a palm tree, lounge chairs, and a railing.

5. 5 bedroom Villa, Pool side Villa, and De Bunk house with Pool, Sleeps 1-8

St Thomas

Andrew R.

￥106,902 total

includes taxes & fees

Sep 29 - Sep 30

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

6. Discover Your Island Oasis: St. Thomas Condo

St. Thomas

Hope and J.

￥92,918 total

includes taxes & fees

Sep 27 - Sep 28

A coastal hotel with a beachfront view, a rocky shoreline, and a backdrop of hills.

7. NEW LISTING- Ideal Oceanside Location and Recent Renovation / DREAM Combination!

St Thomas

Susan R.

￥106,379 total

includes taxes & fees

Oct 9 - Oct 10

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

8. Private Terrace Suite with Ocean Views

Southside

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

￥133,492 total

includes taxes & fees

Sep 28 - Sep 29

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

10. Charming, Hillside Villa with Ocean & Beach Views

Southside

￥103,505 total

includes taxes & fees

Oct 8 - Oct 9

A stone building with a staircase leading to an entrance, surrounded by potted plants and a clear sky.

11. Bluebeard's Castle Resort

Charlotte Amalie

Erica

￥35,915 total

includes taxes & fees

Oct 25 - Oct 26

A coastal landscape with a beach, clear blue waters, and lush greenery.

12. Villa Island Paradise

St. John

Zach Ezekiel Azurus

￥79,387 total

includes taxes & fees

Oct 11 - Oct 12

A beach with clear turquoise water, a sandy shore, and a small island with buildings in the background.

13. Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

St. Thomas

Jason A.

￥31,353 total

includes taxes & fees

Sep 27 - Sep 28

A clear turquoise sea with people swimming.

14. Breathtaking Views from Sapphire Village II

St Thomas

Jason

￥45,383 total

includes taxes & fees

Sep 28 - Sep 29

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

15. The Westin St. John Resort Villas

St. John

"Unfortunately, the pool was under construction during our stay and unusable, but we didn't allow that to stop us. The beach was quite and relaxing, thus Westin has a family vibe and good for children. The staff was friendly. I do think they can do better at advertising the water and children's activities. The rooms were excellent and resturants too. Ferry service and crew were great too. Great stay for a family of 5!"

Shani

￥62,106 total

includes taxes & fees

Oct 10 - Oct 11

A beach with clear turquoise water, sandy shore, and buildings in the background.

16. Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees

St. Thomas

Jessica D.

￥44,924 total

includes taxes & fees

Sep 28 - Sep 29

17. Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

St Thomas

John H.

￥36,392 total

includes taxes & fees

Sep 28 - Sep 29

A living room with a sofa, chairs, a lamp, and a painting on the wall.

18. The Landmark Apartment

St. Thomas

Eileen

￥57,040 total

includes taxes & fees

Oct 11 - Oct 12

19. Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

St Thomas

Quincy

￥37,747 total

includes taxes & fees

Sep 28 - Sep 29

20. The Captain and the Mermaid - Adventures in Paradise are waiting!

St Thomas

Dede C.

￥38,160 total

includes taxes & fees

Sep 27 - Sep 28

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Top Southside Hotel Reviews

The Westin St. Thomas Beach Resort & Spa

10/10 Excellent

"Great stay! Beautiful, BEAUTIFUL scenery! But a bit pricey! Be ready to spend some money! Food at the resort is priceyyyy, so try to eat away from resort. Be sure to have cash because a lot of the taxis may/may not have Cashapp or Zelle to receive payments. Swim up bar was so nice!"

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."

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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Vacation Apartments in Southside

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Look no further and take a look at our great range of rental properties in Southside!

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Southside vacation 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. 5 bedroom Villa, Pool side Villa, and De Bunk house with Pool, Sleeps 1-8

6. Discover Your Island Oasis: St. Thomas Condo

7. NEW LISTING- Ideal Oceanside Location and Recent Renovation / DREAM Combination!

8. Private Terrace Suite with Ocean Views

9. The Perch on Hawkhill, Lower Level

10. Charming, Hillside Villa with Ocean & Beach Views

11. Bluebeard's Castle Resort

12. Villa Island Paradise

13. Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

14. Breathtaking Views from Sapphire Village II

15. The Westin St. John Resort Villas

16. Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees

17. Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

18. The Landmark Apartment

19. Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

20. The Captain and the Mermaid - Adventures in Paradise are waiting!

Find vacation rentals that suit your style

Top Southside Hotel Reviews

The Westin St. Thomas Beach Resort & Spa

Buoy Haus Beach Resort St. Thomas, Autograph Collection

Bolongo Bay Beach Resort

Limetree Beach Resort by Club Wyndham

Sunset Terrace – Epic Views, Pool, & Family Fun!

Oceanfront Villa-walk to resort-Generator & Solar

Villa Mas: Also available as a 3 bedroom.

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

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

Find out more about Southside

Vacation Apartments in Southside

Vacation Rentals in Southside

Change your mind

Treat yourself

Be picky

Our top choices for Southside vacation 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. 5 bedroom Villa, Pool side Villa, and De Bunk house with Pool, Sleeps 1-8

6. Discover Your Island Oasis: St. Thomas Condo

7. NEW LISTING- Ideal Oceanside Location and Recent Renovation / DREAM Combination!

8. Private Terrace Suite with Ocean Views

9. The Perch on Hawkhill, Lower Level

10. Charming, Hillside Villa with Ocean & Beach Views

11. Bluebeard's Castle Resort

12. Villa Island Paradise

13. Modern, furnished condo- Walk to Beach & Marina. Red Hook, Ferry & Bars nearby!

14. Breathtaking Views from Sapphire Village II

15. The Westin St. John Resort Villas

16. Sapphire Sunny Summer Special-1BR Sleeps 4- WIFI -No Excess Owner Fees

17. Paradise @ Sapphire Village Studio- H-S WIFI -No Excess Owner Fees #307

18. The Landmark Apartment

19. Amazing new/modern condo-Walk to beach, Marina and pools. Red Hook/bars near by!

20. The Captain and the Mermaid - Adventures in Paradise are waiting!

Find vacation rentals that suit your style

Top Southside Hotel Reviews

The Westin St. Thomas Beach Resort & Spa

Find out more about Southside

Vacation Apartments in Southside