Waterfront vacation 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.

Private Pickleball Court - 5 min walk to Beach

Does a cozy 3 bedroom vacation rental with a back up generator, 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 a cozy retreat on St. Thomas with all the amenitie

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

Ocean View, Near Town, Backup Power/Strong Wifi

Brand new! Unwind in this stylish, tranquil retreat with breathtaking panoramic ocean views. Feel the Caribbean breeze as sailboats pass & the sun sets over the water. Enjoy sights of St. Croix, Puerto Rico, Water Island, and lush gardens. Minutes from Havensight & Charlotte Amalie, this private retreat features a deck, parking, and a pullout couch. Solar & battery-powered for uninterrupted comfort. Jeep rental available. Beach chairs, cooler, and concierge service included for a seamless stay!

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!

180° Oceanfront Views Sunrise/Sunset From Balcony

****Entire building has GENERATOR**** No passports required to enjoy the sound of waves crashing below a 2 bed/2 bath oceanfront cliffside condo. Take in 180 degree views over the ocean & capture breathtaking sunrises/sunsets from the 500 sq ft balcony. Within the gated community, you will have access to 3 pools and a basketball/tennis court. Bolongo Bay Beach Resort is next door for easy access to snorkel/dive excursions and catamaran cruises. Responsible renters (no parties, please)

Marie’s Oceanfront Condo | 1BR | 3 Pools

Welcome to our beautiful one-bedroom condo at Sea Cliff Villas! Featuring a king-sized bed, a sleeper sofa, a fully equipped kitchen, and a private balcony with breathtaking ocean views. Guests enjoy exclusive access to pickle-ball/tennis courts, 3 fresh-water pools, beach access, and a charming oceanfront restaurant. Nestled on the sought-after south side of St. Thomas, you're close to the island's top beaches and attractions, with the airport just a convenient 15-minute drive away.

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! 🌴

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.

Bolongo Bay Oceanfront•Pool•Beach•Generator

Bring the whole family to the Caribbean in our brand new updated, oceanfront, two bedroom / two bathroom condo on the south side of beautiful St Thomas. Relaxing at Bolongo Bay beach or the pool is only steps away. The property is backed up by a new generator. Enjoy dining at the Caribbean restaurant on property, Mim’s Bistro, Iggie's beach bar, or in the condo with a full kitchen. Pickleball, tennis, and basketball courts available for use next door at Regatta point villas.

Situated above the Caribbean Sea with Beach Access

Tortuga Bliss is perched above the turquoise waters of the Caribbean Sea. During your stay you’ll enjoy breathtaking views and sunsets from your private deck, cruise ships on the horizon and be lulled into a meditative state by the gentle wave action on the diverse rocks and cliffs below. Decorated with quality interiors, linens, bedding and household goods, our goal is to pamper you and provide everything you could need for a memorable Holiday.

Ocean View • Pool • Clean • Couples & Families

Experience serenity at Paradise Palm, a 1BR ocean view condo in gated Sea Cliff Villas. Perfect for couples or small families, enjoy comfort without overpaying for space you don’t need. Walk to beaches, dining, and activities near Bolongo Bay. Relax by the oceanfront pool, and unwind with a full kitchen, Wi-Fi, and Smart TV. A perfect beachside escape with easy access to all St. Thomas offers.