Family-friendly holiday rentals in Southside

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.

Indoor spaces · Family · Quiet

Oceanfront Villa-walk to resort-Generator & Solar

Frenchman’s Breeze: private oceanfront villa on St. Thomas’ Southside with panoramic Caribbean views + snorkeling steps from your door (stairway to the sea). Spacious 2BR/2BA—two king en-suite bedrooms w/ step-in showers. Fully equipped kitchen, open living/dining, and a large terrace with multiple lounge & dining areas. Secluded, serene vibe—no resort crowds—yet minutes to Red Hook dining, shopping nightlife & ferries, and walkable to Limetree Beach Resort. Steep driveway—4WD required. Book now

Indoor spaces · Family · Accuracy

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

Family · Kitchen · Walkability

(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.

Family · Indoor spaces · View

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!

Indoor spaces · Family · View

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!

Kitchen · Indoor spaces · Outdoor spaces

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.

Indoor spaces · Family · Comfort

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! 🌴

Family · Kitchen · Comfort

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.

Family · Kitchen · Checkout

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.

Family · Indoor spaces · Bathroom

Villa View Caribe

Welcome to Villa View Caribe! This stylish-newly renovated villa offers dramatic views and a quiet, comfortable yet refined decor that immediately invites you as the guest to relax and unwind. Once inside this tropical compound, you will immediately experience both a sense of awe at the expansive ocean views as you enter Villa View Caribe. The soaring ceilings encourage you to open your mind to fully experience your next Caribbean Adventure!

Family · Indoor spaces · Pool

Sound of the Sea with Beach and Pools

Welcome to Sound of the Sea, a newly renovated one-bedroom, one-bath condo perfect for your Caribbean escape. Located on St. Thomas’s south side in the gated Regatta Point Villas, enjoy three sparkling pools, tennis/basketball/pickleball courts, and more. Stroll barefoot to Bolongo Bay Beach for the marina, dive shop, Iggy’s Oasis with live music, and the world-famous Mim’s Seaside Bistro, known for its Coconut Curry Lobster!

Beach · Location · Accuracy