Condo holiday rentals in Southside

Sea You Soon Retreat- OCEAN VIEWS, pool, Jeep

Relax with a whole family or group of friends at this peaceful condo overlooking Caribbean Sea. Wake up to ocean views gorgeous sunrises and incredible sunsets.. This amazing rental offers, 3 different pools, tennis & pickleball courts, beach access, 2 oceanfront restaurants walking distance, one with live music, beach access with diving shop. The property is centrally located btw. Charlotte Amalie and Red Hook. The best part is Jeep rental option with complimentary delivery to the airport.

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.

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

Your Piece of Paradise

Enjoy your home away from home in your comfortable SMOKE-FREE condo centrally located on St Thomas. It is within walking distance to Bolongo Bay Resort and Mim’s Seafood Restaurant. Start your day off on your patio looking out at the turquoise water as you sip your breakfast beverage of choice before going to the multi-level pool or the beach with your own beach towels. Then end the day on your KING Tempurpedic Mattress watching your favorite Netflix. This really is your "Piece of Paradise"!

Ocean Serenity! Directly on the Water @Sea Cliff!

Ocean Serenity! Relaxing, tranquil Vacation! Step into this beautifully remodeled 1 BR/1BA condo @Sea Cliff, you are greeted by the breathtaking view and sound of the ocean just a few steps away. Private Balcony to enjoy morning coffee/or drinks during Sunset! 3 pools to enjoy - walk to Bolongo Beach, 2 great restaurants including Mim's Seaside Bistro next door at Watergate and Iggie's Oasis at Bolongo Bay. Bedroom Tucked away so you can sleep in! Open concept living, dining & kitchen.

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!

Corner Pocket Island Retreat

Welcome to your tropical retreat in a secure, gated community. Within walking distance are outstanding restaurants and beach bars including 12 acres of beautiful beach front property, overlooking the white sand beaches of Bolongo Bay and the Caribbean Sea. This beautifully appointed, fully furnished end unit loft condo offers two spacious levels of stylish island living. Enjoy high-end finishes, tasteful furnishings, and cool comfort with the three mini-split A/C units throughout.

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! 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.

*Generator* Ocean-Front Sunsets, Steps 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 embrace island time! Three pools, tennis/pickleball and #OMGViews!

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."