Family-friendly holiday rentals in Southside

A private balcony features two wicker chairs and a round table, providing an inviting space to enjoy the ocean view. The turquoise waters and gentle waves are visible in the distance, complemented by a clear blue sky.

4.94 out of 5 average rating, 139 reviews

So close you can taste the ocean - PRIME Location

Welcome to our FANTASTIC oceanfront condo at Watergate Villas. When it comes to your vacation, as they say in real estate, it's location, location, location! As you can see from our pictures, this unit's prime location is just 30 feet from the OCEAN. If you want to be closer to the water, you are going to need a BOAT. Take a look at the fabulous view from our unit....you will hear the waves every minute of every day. This is the PERFECT location for your stay in America's tropical paradise.

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4.96 out of 5 average rating, 80 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

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4.94 out of 5 average rating, 160 reviews

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

(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.

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Superhost

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

4.92 out of 5 average rating, 108 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!

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4.88 out of 5 average rating, 57 reviews

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

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!

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5.0 out of 5 average rating, 104 reviews

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

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.

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4.96 out of 5 average rating, 169 reviews

A balcony table is set with two plates of breakfast, accompanied by cups, overlooking the tranquil blue waters of the Caribbean Sea. The rhythmic sound of waves enhances the serene dining experience, with a clear sky and fluffy clouds visible in the background.

Condo in Saint Thomas

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 ocean, 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! 🌴

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A private patio features a wooden dining table surrounded by rattan chairs, overlooking the sparkling blue waters of Bolongo Bay. Lush greenery and palm trees are visible in the foreground, complementing the clear sunny sky and tranquil seaside setting.

4.94 out of 5 average rating, 47 reviews

Generator! 4BR remodeled, w/BEACH and 3 POOLS!

Looking for the perfect vacation rental on St. Thomas to kick back, soak up the sun, and live your best island life? Look no further. This stunning, freshly remodeled condo on St. Thomas is perched above the calm waters of Bolongo Bay and ready to welcome you to paradise. Whether you're traveling with family, friends, or just someone who deserves a getaway (that’s you, by the way), this vacation rental on St. Thomas is the ultimate home base for making unforgettable memories.

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A bright living area features large windows revealing ocean views. Natural light fills the space, which includes a sofa, dining table with blue placemats, and decorative plants. A wall-mounted flat-screen TV adds to the modern appeal. The color palette emphasizes calming tones.

4.94 out of 5 average rating, 122 reviews

Sea Dreams at Regatta Point Villas

Regatta Point Villas is located in Bolongo Bay, St. Thomas. This spacious condo (2 full baths and 1 bedroom) features 1000sq.ft. of living space and is located steps away from the pool. It has beautiful ocean views from each room. Bolongo beach is a short walk and has great snorkeling. 2 Tennis Courts, basketball hoop, and 3 pools are all accessible and steps away from the ocean. A short drive to Havensight and Redhook with many beaches and restaurants to choose from.

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Natural light floods the open space from expansive glass windows, framing ocean views. A wooden ceiling adds warmth to the interior, while a staircase leads down to a casual dining area nearby. Clean lines and neutral tones create a serene atmosphere.

4.9 out of 5 average rating, 139 reviews

Sunshine Daydream - Our little piece of paradise!

Spend your days between at Sunshine Daydream with its beautiful ocean views. Rise up to paradise enjoying the gorgeous sunrises and sunsets from the private rooftop deck. This rental offers a fully equipped kitchen, 3 different pools, one of which is steps from the condo. There is easy beach access and we are centrally located between Charlotte Amalie and Red Hook. To top it off there are 2 restaurants and a bar within walking distance from the unit.

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A tranquil pool area is framed by palm trees, with lounge chairs arranged around a clear blue pool. The ocean can be seen in the background, featuring gentle waves and a vibrant sky, enhancing the scenic coastal vista.

4.82 out of 5 average rating, 60 reviews

Ocean-Front 3 Bedroom Villa! Optional SUV Rental

Gorgeous views from this ocean front 3 bedroom villa in St. Thomas USVI. With three spacious bedrooms and sleeper sofa in living room, it is a great value for families and friends to stay together. Newly remodeled, with new A/C system. Cook in or enjoy on-site restaurant for dinner/drinks plus 2 min beach walk to Bolongo Bay Resort for restaurant serving 3 meals, with swim up bar. Steps to pool and beach.

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