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.

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!

Oceanfront w/ Balcony, Pool, Generator & Fast WiFi

🚨Oceanfront Flash Sale—Limited Dates Open🚨 Wake up to the sound of waves and enjoy coffee on your private balcony with stunning sea views. Rare opening at this updated condo with fast Wi-Fi, AC, full kitchen, and backup generator. 5–10 min to beaches, Red Hook dining, and ferries to St. John. Peaceful waterfront stay perfect for couples or remote work. This gap won’t last—book while discounted! All guests are welcome here—we’re proud to share our island home with guests from around the world.

Mermaid Hideaway

Charming ocean view studio located within the quiet, safe Regatta Point Villas (25 min from airport), with private balcony overlooking Bolongo Bay and panoramic views with sunrises and sunsets! Minutes walk to: -Mim’s Seaside Bistro -Bolongo Bay Beach Resort w/ catamaran cruises, kayak rentals, and more -Iggies Restaurant & Bar, live music -The beach: part sand, part rocky but still great! -*1 queen bed, sofa, hutch w/ drawers **Rental unit avail next door for 2 more guests! Inquire within**

"On the Rocks" 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!

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

Private Pickleball Court - 5 min walk to Beach

Does a cozy 3 bedroom vacation rental with 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 your cozy retreat on St. Thomas with all the amenities!

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* Ocean Front Sunsets, Next to 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 fall into island time! Three pools, tennis/pickleball and #OMGViews!

Oceanfront Villa: Stunning Sea Views, Pools, Gated

Experience serenity at Paradise Palm! Nestled in the gated Sea Cliff Villas, our condo offers breathtaking ocean views and a secluded yet central location right on the Caribbean Sea. Enjoy a clean, comfortable home with a stocked kitchen and bath, high-speed Wi-Fi, Smart TV, and a fabulous pool overlooking the sea. Beaches and dining are within walking distance, and nearby, you'll find exciting water sports and island activities. Your tropical escape awaits!