Holiday houses in Southside

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Top-rated holiday rentals in Southside

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Guest favourite

An aerial view of the Villa Royale displays the spacious layout of the property, featuring a blue roof and white exterior. The pool area is visible at the top, surrounded by lounge chairs, while landscaped grounds with pathways lead towards the entrance.

Villa in Southside

4.92 out of 5 average rating, 24 reviews

Villa Royale

Welcome to beautiful Villa Royale (formerly Villa La Creole)! Come indulge in the tranquility and comfort of this open-concept Villa. Tiled floors, high beamed ceilings, and filled with tasteful furnishings and decor. Enjoy the breathtaking views of the Caribbean Sea and relax to the sounds of crashing waves. Gaze at the colors that fill the sky at sunset. Unwind poolside and take a dip. The villa is located in Frenchman’s Bay close to shops and restaurants. Villa Royale, your serene getaway!

Guest favourite

A spacious living area features large windows allowing for abundant natural light and ocean views. Comfortable seating is provided on a light-colored sofa, paired with a distinctive wooden coffee table. Decorative wall art and a floor lamp add character to the inviting atmosphere.

Condo in Southside

4.96 out of 5 average rating, 73 reviews

Oceanfront luxury penthouse

Fall asleep listening to the waves in our sunny & spacious 2-bedroom loft with panoramic 180-degree ocean views making it easy to let the sea breeze & natural sunlight fill the space. Gorgeous high-end furnishings, a fully-equipped kitchen & plenty of comfortable spots to relax. Each bedroom has an ensuite bathroom - perfect place for couples or families wanting to relax and explore ST. Quiet gated community 3 pools & a short walk to 3 restaurants including the famous Iggies Beach Bar. Paradise

Guest favourite

A serene ocean view is presented from a patio, featuring soft waves gently lapping at a sandy beach. Lush greenery and lounge chairs are visible on the shore, while a palm tree sways in the foreground under a bright blue sky with scattered clouds.

Guest suite in Southside

4.94 out of 5 average rating, 150 reviews

(Upper Level) Peaceful Getaway in Frenchman Bay

Indulge in the serenity of our Rock City retreat, where breathtaking ocean views meet refined comfort. Enjoy the patio, WiFi, AC, and eco-friendly solar energy. Ideally situated for families and travelers alike, our haven is close to Morningstar Beach, Westin conferences, and Havensight shopping. For added convenience, rent an SUV or utilize taxi services. Click on our Group Villa listing which offers ample space for up to 15 guests. For a seamless stay, review listing details and house rules.

Guest favourite

A beachfront view captures the clear turquoise waters lapping against a rocky shore. Lush palm trees sway gently in the foreground while various buildings line the beach. Rolling green hills rise in the background under a bright blue sky with scattered clouds.

Condo in Southside

4.94 out of 5 average rating, 127 reviews

Stay in Style right on the Ocean -Simply the BEST!

Take a look at the fabulous view from our unit, you will hear the waves every minute of every day. Your patio is so close to the ocean that you can actually throw a coconut and hit the water. I have done it! This is the PERFECT location for your stay in America's Tropical Paradise. We are constantly doing updates & recently added a new memory foam sofabed, new king mattress, new patio set and new stove all in Jan. 2026. You will NOT find a nicer condo for this price anywhere on the island.

Guest favourite

An open living area features a blue sectional sofa, complemented by a decorative round coffee table. The bright kitchen area includes white cabinetry and modern appliances. Natural light filters through the windows, enhancing the cozy atmosphere, while indoor plants add a touch of greenery.

Apartment in Southside

4.94 out of 5 average rating, 101 reviews

Hidden in Havensight! Guest Favorite 2BD/2BA

Centrally located 2 BR/2 BA, “Hidden Jewel” accommodates your every need. You’ll be steps away from Havensight Mall area with great shopping, restaurants & more. A 2 min walk to Skyride Tramway, 7 min walk to Yacht Haven Grande & a mile away from downtown Charlotte Amalie. Most importantly, you’ll be at most a 20 min drive to beautiful beaches. Feeling adventurous? Take a 15 min drive to Red Hook where you have access to a 15 min ferry ride to St. John! Everything you need plus great weather!

Top Guest favourite

A spacious deck features wooden flooring and a wooden ceiling supported by blue beams. Outdoor furniture includes a sectional couch with a red accent pillow, a coffee table, and a dining set. Views of the surrounding hills and the Caribbean Sea are visible in the distance.

Home in Southside

4.93 out of 5 average rating, 91 reviews

Recently Built House! - 3/3 w/ Amazing View & Deck

Just completed construction of a brand new 3 bed/3 bath house on the South Side of St Thomas. Centrally located close to beaches and restaurants. Modern amenities, high-end furniture, well insulated with cool air conditioning, huge 600 square foot deck with amazing view of the Caribbean. Two of the bedrooms have en-suite baths. Automatic backup generator. Additionally an SUV is offered through Property Manager. This House is brand new modern comfort located in the heart of paradise!

Superhost

A spacious living area features a light, neutral sofa adorned with green cushions. Large windows provide ocean views and ample natural light, while a white coffee table sits in the center. The ceiling showcases wooden beams, contributing to the open and airy atmosphere.

Home in Southside

4.84 out of 5 average rating, 45 reviews

Villa Breizh- Spacious 3 Bdrm- 3 Bath

Villa Briezh, located on St. Thomas's Southside, is a stunning retreat just a short walk from Abi Beach (7 mins) and Limetree Beach Resort (10 mins) with 2 restaurants, and beach access. This spacious, beautifully furnished condo offers 3 bedrooms, 3 bathrooms, a fully equipped kitchen, and a washer/dryer. Enjoy breathtaking ocean views from the amazing deck and benefit from free parking right outside the unit. Villa Briezh combines luxury and convenience for the ultimate island escape!

Guest favourite

A sparkling blue pool is framed by tropical palm trees and lounge chairs, set against panoramic views of the ocean. Umbrellas provide shade for seated guests, while the clear sky enhances the inviting atmosphere of this outdoor space.

Villa in Southside

4.96 out of 5 average rating, 71 reviews

Frenchman's View Villa 2 BD/2.5 BA w/ Pool

Breathtaking sunset and ocean views from this gorgeous villa nestled among the trees in paradise. A generous living space with oversized sectional effortlessly flows into the outdoor patio and pool area, perfect for sunbathing, a BBQ with friends and family, or a cocktail under the shaded cabana area. 2 fully air-conditioned bedrooms and 2.5 baths round out this fabulous property! Minutes to Havensight, Yacht Haven Grande, Charlotte Amalie, and a variety of shops and restaurants!

Top Guest favourite

An outdoor infinity pool is shown with tranquil waters extending towards the Caribbean Sea. Lush greenery and palm trees surround the area, with views of the coastline and sailboats on the horizon. The sky is partly cloudy, enhancing the serene atmosphere of the setting.

Home in Southside

5 out of 5 average rating, 100 reviews

Entire villa with beautiful views! Amazing

Overlooking Bolongo beach. Perfect for couples traveling together but want plenty of privacy as well. 1200 sf covered patio to enjoy sunning, relaxing, dinners with family and friends while being soothed by waves and wonderful breezes. Two bedrooms, each with full baths in main house AND two private apartments below each having the same wonderful views! Perfectly located between Red Hook for ferry to St. John and Havensight for shopping. Catch the beautiful sunrises and sunsets.

Guest favourite

A modern building is surrounded by lush greenery and features a landscaped pathway leading to a spacious deck. Cozy seating areas are arranged around a jetted swim spa, creating an inviting outdoor space overlooking the scenic hills.

Home in Southside

4.88 out of 5 average rating, 26 reviews

Private Pickleball Court - 5 min walk to Beach

Does a cozy 3 bedroom vacation rental with its own 17' lounge pool that's walking distance to Limetree Beach, Lanaii restaurant, and has a pickleball court, sound like your ideal vacation rental? Well, hi there! Welcome to Villa Hygge (hoo-gah)! We are conveniently located between Red Hook and Havensite, for restaurants and shopping. You are only 15 minutes to the St. John ferry and beautiful east end beaches. Villa Hygge is your cozy retreat on St. Thomas with all the amenities!

Top Guest favourite

The living area features a spacious sofa and a patterned armchair arranged around a coffee table. Large sliding glass doors provide a view of the ocean and access to the balcony. A dining table with chairs is positioned near the window, allowing for bright natural light.

Condo in St. Thomas

4.96 out of 5 average rating, 157 reviews

Oceanfront Bliss & Perfect Sunsets + Backup Power

Our fully renovated 1BR/1BA condo is PERFECT for couples, small families or a friends getaway. Enjoy stunning ocean views and the sound of waves from every room or your private balcony. Watch breathtaking sunsets and cool off in one of three crystal-clear pools. Located in a gated community, just steps from the beach, oceanside pool, and seaside dining. Only 10 min to Red Hook (ferries to St. John & BVI) and Havensight, and 15 min from the airport—your perfect island escape! 🌴

Guest favourite

A spacious bedroom features large glass doors opening to a balcony with ocean views. A king bed with a floral-patterned coverlet is complemented by bedside tables with lamps. Bright teal walls and ceiling fan provide a calming ambiance, while white tile flooring enhances the room's brightness.

Condo in Southside

4.91 out of 5 average rating, 11 reviews

2024 Remodel • W/D • King • Generator • Pickleball

Breathe in the Caribbean Sea breeze from your bedroom and watch yachts sail by! Welcome to your “Paradise View House!” Key Highlights: ☞ Newly Renovated (completed) ☞ Onsite Generator ☞ King Bed ☞ Fast Wifi & Office Desk ☞ Washer & Dryer in Unit ☞ 10 mins to Red Hook ☞ Parking Available ☞ Secure Gated Entrance ☞ Short Walk to Bolongo Beach ★ "To start Heidi was the most responsive airbnb host I’ve ever dealt with. From start to finish I felt valued and respected."