Waterfront holiday rentals in Southside

Amazing Sea Cliff Views 2 bed 2 bath 3 pools beach

Where Bolongo bay meets the Caribbean. Relax in this beautifully renovated 2-bedroom 2-bath villa. This unique corner unit at Sea Cliff Villas has amazing views from virtually every room. The spacious main bedroom with a 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 with generator!

Hidden in Havensight! Guest Favorite 2BD/2BA

Centrally located 2 BR/2 BA, “Hidden Jewel” accommodates your every need. You’ll be steps away from Havensight Mall area with great shopping, restaurants & more. A 2 min walk to Skyride Tramway, 7 min walk to Yacht Haven Grande & a mile away from downtown Charlotte Amalie. Most importantly, you’ll be at most a 20 min drive to beautiful beaches. Feeling adventurous? Take a 15 min drive to Red Hook where you have access to a 15 min ferry ride to St. John! Everything you need plus great weather!

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.

Frenchman's View Villa 2 BD/2.5 BA w/ Pool

Breathtaking sunset and ocean views from this gorgeous villa nestled among the trees in paradise. A generous living space with oversized sectional effortlessly flows into the outdoor patio and pool area, perfect for sunbathing, a BBQ with friends and family, or a cocktail under the shaded cabana area. 2 fully air-conditioned bedrooms and 2.5 baths round out this fabulous property! Minutes to Havensight, Yacht Haven Grande, Charlotte Amalie, and a variety of shops and restaurants!

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

Walk to the Beach - POOL - Pickleball Court!

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!

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."

Palm Vista - new 3 bedroom, 3 bath condo ocean

This incredibly spacious 3 bedroom/3 bathroom condo located at Sea Cliff Villas is newly renovated. Enjoy the 180-degree ocean view from the two gorgeous balconies! The fully equipped kitchen has bar seating and a large dining table. The condo comfortably sleeps 6 guests with three bedrooms that have king beds. Beautiful property with brand new tennis/basketball courts and access to 3 pools, and 2 restaurants. Back up generators for any island power outages.