Holiday rentals with a pool in Southside

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**

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.

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!

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!

Sunshine Daydream - Our little piece of paradise!

Spend your days between at Sunshine Daydream with its beautiful ocean views. Rise up to paradise enjoying the gorgeous sunrises and sunsets from the private rooftop deck. This rental offers a fully equipped kitchen, 3 different pools, one of which is steps from the condo. There is easy beach access and we are centrally located between Charlotte Amalie and Red Hook. To top it off there are 2 restaurants and a bar within walking distance from the unit.