Holiday rentals with outdoor seating in Southside

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.

(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.

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**

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.

"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!

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

Oceanfront Sunrise Escape + Backup Power & 3 Pools

Welcome to your Caribbean oceanfront escape! This renovated condo was designed for the perfect island retreat, set in a secure gated community. Enjoy sunrise views and relax with a swim in one of three sparkling pools. In just two minutes you can stroll to Bolongo Bay Beach to snorkel, swim, or simply unwind by the sea. Whether you crave pure relaxation or a hint of adventure, this condo offers it all—complete with modern comforts, backup generator, and unforgettable island vibes.

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! 🌴

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.

Ocean View in Paradise- King Bed-3 Pools-No Stairs

Welcome to our tranquil oasis at Regatta Point Villas! Experience modern elegance in our charming studio apartment with a plush KING-SIZE bed and FULL SLEEPER SOFA. Enjoy amenities like 3 pools, tennis/pickle ball court, and an ocean front restaurant all on property! Prepare your favorite meals in the well-appointed kitchenette! Dine al fresco on the charming balcony overlooking the shimmering ocean! Quick 15 min drive from the airport! Perfect for your next getaway!

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!