Condo vacation rentals in Southside

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Top-rated condo rentals in Southside

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Guest favorite

An aerial view captures the three pool areas, surrounded by lush tropical greenery. Sun loungers are arranged around the pools, which glisten under the sunlight, with the Caribbean Sea visible in the background. The landscape features palm trees and colorful plant arrangements.

Condo in Southside

4.94 out of 5 average rating, 18 reviews

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.

Top guest favorite

A clear view of the ocean is presented, showcasing turquoise water gently lapping against the shore. A small boat floats on the water, while waves create a soft white foam. The horizon stretches into the distance, blending with a blue sky dotted with a few clouds.

Condo in Southside

4.94 out of 5 average rating, 124 reviews

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.

Guest favorite

Condo in St. Thomas

4.95 out of 5 average rating, 127 reviews

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.

Guest favorite

A private balcony offers views of the ocean, where waves crash against the shore. Two chairs and a table are positioned to enjoy the scenery, complemented by a clear blue sky and gentle cloud cover.

Condo in St. Thomas

4.95 out of 5 average rating, 64 reviews

Villa Crystalia Oceanside condo

Relax and take in the views and sounds of this brand new stunning seaside villa. Listen to the waves and watch the ship and boat traffic pass by your balcony. Centrally located, with Charlotte Amalie and Red hook only a quick ten minute drive. Enjoy pool and tennis courts on site with great restaurants close by. Villa is equipped with mini split AC’s and new appliances, including washer and dryer. All linens and towels provided. Beach chairs, a cooler and tennis rackets are available for use.

Top guest favorite

Condo in Southside

4.99 out of 5 average rating, 82 reviews

Mermaid Hideaway

Charming ocean view studio located within the quiet, safe Regatta Point Villas (25 min from airport), with private balcony overlooking Bolongo Bay and panoramic views with sunrises and sunsets! Minutes walk to: -Mim’s Seaside Bistro -Bolongo Bay Beach Resort w/ catamaran cruises, kayak rentals, and more -Iggies Restaurant & Bar, live music -The beach: part sand, part rocky but still great! -*1 queen bed, sofa, hutch w/ drawers **Rental unit avail next door for 2 more guests! Inquire within**

Guest favorite

A serene view of a bright blue pool surrounded by a wooden deck, positioned near the edge of a calm ocean. Lush palm trees and vibrant pink bougainvillea add color to the scene, enhancing the relaxing atmosphere. The clear sky complements the tranquil water.

Condo in Southside

4.9 out of 5 average rating, 30 reviews

Amazing views,touch the waves from the balcony !

This unique place has a style all its own. Newly renovated with full Kitchen and laundry. Situated right on the beach with beautiful views of the ocean and sunsets . Perfect for romantic get away for 2 , but can accommodate up to 2 children as well! Has 2 pools and tennis court , conveniently located , only 15 min from airport or 15 min to St. John ferry from Redhook. Attention: Our resort has fully automatic generator, that is very important on our island since electricity goes off a lot !

Top guest favorite

A private balcony offers a blue view of the ocean, with waves gently lapping against rocky shores. The scene includes a bistro table and chairs in a matching blue, inviting relaxation and enjoyment of the coastal surroundings under a clear sky.

Condo in Southside

5 out of 5 average rating, 14 reviews

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.

Guest favorite

A spacious living area features a comfortable sofa facing a flat-screen television. Natural light enters through sliding glass doors, connecting the indoors to the ocean view outside. A dining table with seating and modern decor complement the open layout, creating an inviting atmosphere.

Condo in St. Thomas

4.98 out of 5 average rating, 43 reviews

Beautiful Ocean Views/Amazing Sunsets/three pool!

Relax in this beautifully designed, comfortable 1bdrm/1bath ocean view condo at Sea Cliff Villas. Comfortably furnished, spacious with modern décor, sofa bed and pack & play. Fully equipped kitchen w/private balcony only steps from the ocean! Watch the ships, boats, surfers & beautiful sunset from your balcony! Relax to the peaceful sounds of the ocean. Steps away from Iggie's and Mims restaurants & Bolongo Bay Beach. Access to 3 pools, tennis court, parking w/backup generator onsite.

Guest favorite

An aerial view captures the inviting pool area surrounded by lush greenery, with several lounge chairs arranged around a large circular pool. The ocean glimmers in the background, while the adjacent coastline features gentle waves and a picturesque landscape.

Condo in Southside

5 out of 5 average rating, 6 reviews

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.

Guest favorite

A dining area is presented with a marble-top table surrounded by brown chairs. A decorative bowl with fruit sits at the center, while large windows provide views of the ocean and greenery outside. Natural light fills the space through the glass doors leading to a balcony.

Condo in Southside

4.93 out of 5 average rating, 41 reviews

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.

Guest favorite

The image captures a serene view of a multi-level pool surrounded by lush greenery and palm trees. The expansive blue ocean glimmers in the background under a clear sky, while sun loungers are positioned around the pool, inviting relaxation.

Condo in Southside

4.92 out of 5 average rating, 106 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.

Guest favorite

Condo in St Thomas

4.93 out of 5 average rating, 43 reviews

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.