Family-friendly vacation rentals in Southside

4.93 out of 5 average rating, 135 reviews

Guest suite 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.

4.96 out of 5 average rating, 145 reviews

Condo in St. Thomas

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.

4.94 out of 5 average rating, 125 reviews

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.

4.97 out of 5 average rating, 58 reviews

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

5 out of 5 average rating, 61 reviews

Apartment in Southside

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.

4.95 out of 5 average rating, 108 reviews

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.

Superhost

Guest suite in St. Thomas

4.83 out of 5 average rating, 96 reviews

The Artsy' Studio for solo travellers

The Artsy' Studio is located at a Tropical Island house with a perfect ambiance at a lower hillside. Independent entrance for you alone at the main home in a secure safe upscale exclusive residential area surrounded by lush gardens and endless Light Blue Caribbean Seaviews A short drive to the best shopping area and the Port of Havensight & Yacht Haven Grande Marina Approximately 15 min. from the airport Welcoming easy going Solo's for short stays !

5 out of 5 average rating, 47 reviews

Peaceful Oceanfront Oasis / 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. Enjoy dining at the Caribbean restaurant on property, Mim’s Bistro, or in the condo with a full kitchen. Pickleball, tennis, and basketball courts available for use next door at Regatta point villas. The property is backed up by a new generator.

Superhost

4.89 out of 5 average rating, 114 reviews

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.

Superhost

Home in Southside

4.77 out of 5 average rating, 60 reviews

Regatta Point! Ocean View Condo!

Regatta Point Villas is situated in a secured gated community in bolongo bay St. Thomas. Very spacious studio! Everything is brand new! Appliances etc…Very clean and comfortable! Newly renovated! You can see & hear the ocean from inside! Cable TV, Excellent WiFi. Close to Red hook (10 minutes) and downtown (15 minutes) Excellent location! Hot & Cold water in bathroom and kitchen.

5 out of 5 average rating, 23 reviews

Condo in St Thomas

Oceanfront, 3 POOLS, Central Location, Generator!

Searching for the perfect condo on St. Thomas, near restaurants, beaches, shopping, pools, and the ferry to St. John? Well, look at that—you’ve found us! Your dream vacation starts here at On the Rocks St. Thomas, a fully updated vacation rental on St. Thomas that combines modern luxury, family-friendly amenities, and an unbeatable oceanfront location near Red Hook and Havensight.