Holiday rentals in Southside

(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.

Oceanfront Condo Perfect Sunsets Backup Generator!

Our completely renovated one bedroom, one bathroom condo is PERFECT for couples, small families or a friends getaway. See the ocean and hear the waves from every room. Beautiful views, sounds, and location with private balcony. Centrally located, in a gated community, to some of the best beaches in the world and only 10 minutes from Red Hook (Ferries to St. John & BVI), Havensight (Cruise ship docks) and about 15 minutes from the airport. Steps to the oceanside pool, beach, and seaside dining.

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!

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!

Newly Renovated Oceanfront Condo

Welcome to your perfect Caribbean island getaway! Meticulous planning and very careful thought have gone into this fully renovated oceanfront condo in the gated community of Sea Cliff Villas. Take a relaxing swim in one of the 3 gorgeous pools located within the community. You can take a short 2 minute walk to enjoy Bolongo Bay Beach, where you can swim, snorkel or just sit back and enjoy the beautiful view. This is your perfect opportunity to satisfy your taste for adventure!

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.

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.

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.

2 oceanfront suites with water access! Solar/batt

Frenchman’s Breeze 🌊 is a beautiful oceanfront villa on the Southside of St. Thomas 🌴 just minutes from Red Hook and Charlotte Amalie 🛍️. Enjoy 10% off stays of 5+ nights 💸. This 2-bedroom, 2-bath 🛏️🚿 property features king en-suites, a full kitchen 🍽️, spacious living/dining areas 🛋️, and a large terrace 🌅 overlooking the Caribbean Sea. Direct ocean access via private stairs makes it perfect for snorkeling 🤿 and relaxing in total privacy.