Waterfront holiday rentals in Southside

Oceanfront Villa-walk to resort-snorkle from home

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 spotless 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!

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!

Regatta’s Island Time Getaway

Escape to Regatta’s Island Time Getaway for the Ultimate Waterfront experience! With stunning ocean views, crystal clear waters, and all the amenities you need, this rental is the place! it is perfect for a romantic retreat or a fun family vacation. Spend your days lounging by the pool, exploring the island with the best snorkeling or enjoying the local restaurants and bars. Book your stay today and make some memories that will last forever while experiencing island living on St. Thomas USVI!

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 just finished updating this unit in April ‘21 with new kitchen tile, new fridge, new cookware, dishware and kitchen utensils, Smart TV. You will NOT find a nicer condo for this price anywhere on the island.

Escape the Cold/Ocean Front/1BR/1BA/Amazing Views/

Beautifully remodeled & stylishly furnished. 1BR/1BA condo w/amazing ocean & sunset views! "On the Rocks" is directly on the ocean w/an incredible ocean breeze. Hear the sound of the ocean waves crashing below as you enjoy sunset on your own private patio. Watch sailboats, ferries, and cruise ships pass by as you enjoy your favorite cocktail! This beautiful St. Thomas condo is centrally located in a gated community between Downtown Charlotte Amalie and Red Hook. The Perfect Location!

Coral cove studio - ocean view

This apartment offers floor-to-ceiling views of the majestic Caribbean Sea from its south-facing windows. The studio has a full kitchen, a ocean faced balcony and a cozy beachy vibe. Enjoy the warmth of glorious sunrises and sunsets, watching the amazing cruise ships pass by right outside the windows. Enjoy one of the three pools, the tennis court or the beach within walking distance! Centrally located on the island. Easy to take a taxi only 10-15 minutes to downtown or to redhook!

Marie's Gorgeous Oceanfront Condo-1 Bdrm-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 luxury penthouse

Fall asleep listening to the waves in our sunny & spacious 2-bedroom penthouse loft with 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 the beach & two restaurants. Enjoy our paradise

Klarissa’s by The Sea by Villa Sunbeam.

Klarissa’s by the Sea is a comfortably furnished and unique 1BR/1BA unit located at popular Villa Sunbeam in St. Thomas. It’s peaceful setting with distinctive Harbour Views and near town location offers easy walkable access to dining, attractions and activities in the Havensight area. With a polished new look, this carefully appointed space is perfect for remote working or a leisure getaway with its convenient to town location. Welcome to “Klarissa’s by the Sea” in St. 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 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! 🌴

*Generator* OceanFront Sunsets, Steps from Pool!

Welcome to Siren's Point! Beautifully remodeled 1BR/1BA condo with amazing views! Grab a cocktail and take in an island sunset while listening to the waves crash below your private balcony! Sea Cliff Villas, a gated community on the Southside, is centrally located between downtown Charlotte Amalie and Red Hook... Easy to get to all the best beaches, restaurants and shopping! Everything is ready for you to enjoy island time! Three pools, tennis/pickleball and #OMGViews!