Condo 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.

Seaside Calm at Paradise Palms

Located in a private gated community on the island’s centrally-located southside, this peaceful escape allows you to choose between the quiet solitude of endless ocean views in Paradise, or tropical adventures ziplining the jungle northside, historical tours in Charlotte Amalie, shopping in Havensight, dining in Yacht Haven Grande, or dancing the night away in Red Hook after a day boating around St. John. Regatta Point is home to 3 pools, a tennis/pickleball court, 2 beaches, and 2 restaurants.

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

180° Oceanfront Views Sunrise/Sunset From Balcony

****Entire building has GENERATOR**** No passports required to enjoy the sound of waves crashing below a 2 bed/2 bath oceanfront cliffside condo. Take in 180 degree views over the ocean & capture breathtaking sunrises/sunsets from the 500 sq ft balcony. Within the gated community, you will have access to 3 pools and a basketball/tennis court. Bolongo Bay Beach Resort is next door for easy access to snorkel/dive excursions and catamaran cruises. Responsible renters (no parties, please)

*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 relax and enjoy island life! Three pools, tennis/pickleball and #OMGViews!

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 ocean, 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! 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.

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.

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.

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."

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.

Situated above the Caribbean Sea with Beach Access

Tortuga Bliss is perched above the turquoise waters of the Caribbean Sea. During your stay you’ll enjoy breathtaking views and sunsets from your private deck, cruise ships on the horizon and be lulled into a meditative state by the gentle wave action on the diverse rocks and cliffs below. Decorated with quality interiors, linens, bedding and household goods, our goal is to pamper you and provide everything you could need for a memorable Holiday.