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.

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

Amazing Sea Cliff Views 2 bed 2 bath 3 pools beach

Where Bolongo bay meets the Caribbean. Relax in this peaceful oceanfront 2-bedroom 2-bath villa. This unique corner unit at Sea Cliff Villas has amazing views from virtually every room. Huge main bedroom with king size bed, full bath,walk in closet, sitting area , balcony and ocean view. Even the guest room has an ocean view. Living room has a air dream sofa sleeper with ocean view. Two balcony’s to watch the ships pass by. Full kitchen & outdoor cooking area. Gated private oasis with generator!

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!

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 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! 🌴

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.

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.

Three Little Sandpipers – Oceanfront!

Oceanfront! New remodel! This beautiful, 2-bedroom, 2-bath condo, “Three Little Sandpipers", is located in Watergate Villas in Bolongo Bay. It is steps away from beach, pool and restaurant/bar access. Bolongo Beach is walking distance and has excellent snorkeling. Centrally-located 20 minutes from the airport and 10 minutes between Havensight and Redhook with many beaches and restaurants to choose from. Come relax and enjoy the breezy island right outside your front door!

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."