Top Vacation Homes in Southside in 2026

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Our top choices for Southside vacation homes

A terrace with chairs and a table, overlooking a coastal cityscape at dusk with illuminated buildings.

1. 3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor

Frenchman's Bay, St. Thomas

Douglas B.

A coastal hotel with a beach view, clear turquoise waters, and lush greenery.

2. Darling Palms Retreat: Beachside 2-Bedroom Oasis

ST THOMAS

Evan L.

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

3. Charming, Hillside Villa with Ocean & Beach Views

Southside

AED 2,395 total

includes taxes & fees

23 Oct - 24 Oct

A table set for two with dark plates, clear glasses, and a small potted plant.

4. Escape to Paradise! Ocean View, Convenient Location, Solar/Backup Power/WIFI

St Thomas

Connor B.

A beach with lounge chairs and umbrellas, a hotel in the background, and a pier extending into the water.

5. Amazing views and great location - 4 Bedroom Estate Bakekroe in St Thomas

St Thomas

Cielo F.

A resort with a beach, a swimming pool, and several buildings with blue roofs.

6. Villa Breizh- Spacious 3 Bedroom

St Thomas

Edward B.

A kitchen with wooden cabinets, a white stove, and a window providing natural light.

7. Beautifully Renovated 3 Bedroom Home with 2 Bathrooms Centrally Located

St. Thomas

A flat-screen TV on a wooden cabinet, a window with a view, and a patterned curtain.

8. Coral Cottage Cove-Amazing Ocean Views - 3 Bedroom 2 Bath in St. Thomas

St. Thomas

Lou G.

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Top Southside Hotel Reviews

Hampton by Hilton St. Thomas

10/10 Excellent

"I wish it had a balcony to over look the harbor"

Limetree Beach Resort by Club Wyndham

8/10 Good

"Here are the important things you need to know about the Windham Limetree Beach resort: First off, the grounds are beautiful. It's a super nice facility that has an open feel, it is well kept, and the rooms are nice - 20 seconds from the beach. The swim up pool bar is fun with good drinks/food. The property is private, safe, and even at full occupancy, does not feel crowded. So here is the zinger: This is a “timeshare” (Windham Beach Club). Ok, not a big deal so far. Just be aware that when you check in, you will have to sit down with the “concierge” (not a real concierge, but more of a sales person) to get your room key. This person was very nice and offered a few tips on the area but was primarily there to convince you to go to a timeshare sales meeting. What!! I didn't even know was this was a timeshare. She will keep you for 20-30 minutes until she feels that there is little chance to get you to agree to the “sales presentation”. She will offer room nights at other locations, food, gifts etc. to agree to go the 2 hour session. I don't know about you, but I hate being passively pressured to buy stuff. BUT, no matter what you do, don't give them your cell phone number. They wanted my number to send me “updates on my room”. Well what I got texts and calls that was just more pressure to attend the sale presentations. That continued for WEEKS after my stay. This is a beautiful property – go there, but don't give them your phone number."

Bolongo Bay Beach Resort

10/10 Excellent

"This is as small property with a laid back vibe. Not your typical all inclusive resort. It is an older property and dated but that is what gives it charm. The only complaint is the small shower, but we knew about that prior to our visit. No biggie! Rooms are very clean! The staff are great and the food is hands down the best we have ever had at an all inclusive. It is not gourmet, but good food done well! No buffets here! Make sure you meet Big Dog at Iggies. If she does not put a smile on your face, no one will! Then you have Rosie, the resort dog! She is just the sweetest and adds little extra to your stay! Highly recommend Jermaine with Island Life Jeep Tour! He is great, knows the island and it's history. Your day is all customized to what you want to do! We will be back soon for sure!"

Boundless Bliss Hotel

10/10 Excellent

"Rooms were clean and insect free, quiet atmosphere and beautiful view of island plus your in the middle of both sides of were the beaches are 6 minute drive to either side of the things to do, middle of the beaches which are located on both sides of the island and Quiet away from the busy streets and up high"

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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Check prices for these dates

Our top choices for Southside vacation homes

1. 3 Bedroom House and Pool with Spectacular views of Charlotte Amalie Harbor

2. Darling Palms Retreat: Beachside 2-Bedroom Oasis

3. Charming, Hillside Villa with Ocean & Beach Views

4. Escape to Paradise! Ocean View, Convenient Location, Solar/Backup Power/WIFI

5. Amazing views and great location - 4 Bedroom Estate Bakekroe in St Thomas

6. Villa Breizh- Spacious 3 Bedroom

7. Beautifully Renovated 3 Bedroom Home with 2 Bathrooms Centrally Located

8. Coral Cottage Cove-Amazing Ocean Views - 3 Bedroom 2 Bath in St. Thomas

9. Bellevue Horizon Villa: Luxurious Island Retreat with Stunning Views & Pool

10. Private Resort Experience | Arcade + Gym + Pool

11. 4BR Prime location, Ocean view, Backup Power, Strong Wifi, Jeep Rental Available

12. Panoramic Ocean View.

13. FULL RESORT ACCESS! Marriott Two Bedroom Suites with full kitchen

14. Misty's Point of View

15. Walk to Beach + Dining | Private Pickleball Court

Find vacation rentals that suit your style

Top Southside Hotel Reviews

Hampton by Hilton St. Thomas

Buoy Haus Beach Resort St. Thomas, Autograph Collection

Limetree Beach Resort by Club Wyndham

Bolongo Bay Beach Resort

Boundless Bliss Hotel

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!

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