Vacation rentals with a pool in Southside

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Top-rated rentals with a pool in Southside

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

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 tranquil pool area is framed by tall, swaying palm trees, with lounge chairs arranged along the water's edge. The pool reflects the surrounding greenery and is set against a backdrop of calm waters and a distant rocky shoreline.

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.

Superhost

An aerial view captures the spacious patio featuring a refreshing pool, surrounded by lounge chairs and vibrant flowers. The surrounding hillside and ocean can be seen in the background, showcasing the property's elevated location and scenic views.

Villa in Southside

4.71 out of 5 average rating, 7 reviews

Southside 4BR/2.5BA

A spacious multi unit villa. Designed as a corporate retreat for executives, traveling with their family or friends. Four bedrooms king master with in-suite bathroom, three other bedrooms, two with two queen beds each and a third with a single queen share the 1.5 baths. The Half bath located in the dual living space with queen sleeper sofa not far from the fully equipped kitchen and open plan living/dining spaces. An ocean view deck completes this unit offering views of the pool below as well.

Guest favorite

An inviting ocean-side pool is surrounded by a spacious deck with several lounge chairs and tables. Clear blue water reflects the sunlight, while the vast ocean extends beyond the pool area, providing a stunning backdrop.

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

Condo in St Thomas

4.93 out of 5 average rating, 43 reviews

Ocean-Front w/ *Generator* - Right next 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 relax and fall into island time! Three pools, tennis/pickleball and #OMGViews!

Guest favorite

A jetted pool is framed by a spacious deck, overlooking a scenic view of the ocean. Comfortable seating is arranged nearby, inviting relaxation. The clear sky and sunlight enhance the tranquil atmosphere of this outdoor space.

Home in Southside

5 out of 5 average rating, 7 reviews

Breathtaking 3/2 Villa, walk to Limetree Resort

Welcome to this beautiful, newly built,3 bed,2 bath Villa, with a 17' jetted pool & back up Solar system. The property has the perfect mix of relaxation, comfort & privacy. We are located just above Limetree Resort on the South Side of the Island. **THIS PROPERTY HAS BEEN LISTED ON AIRBNB FOR 2 YEARS & RECENTLY SOLD. WE HAD TO START A NEW LISTING AND WERE NOT ABLE TO TRANSFER THE 30,5 STAR REVIEWS, THAT WE HAVE RECEIVED. I HAVE POSTED PICTURES OF THE REVIEWS UNDER "ADDITIONAL PHOTOS"

Guest favorite

An outdoor space featuring a sparkling pool surrounded by lounge chairs and a covered seating area. A stainless steel grill and lush palm trees are included, with scenic mountain and ocean views in the background under a partly cloudy sky.

Villa in Southside

4.95 out of 5 average rating, 63 reviews

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!

Guest favorite

A private patio features a wooden dining table surrounded by rattan chairs, overlooking the sparkling blue waters of Bolongo Bay. Lush greenery and palm trees are visible in the foreground, complementing the clear sunny sky and tranquil seaside setting.

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

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

A serene pool area is surrounded by lush green foliage, providing a natural frame. White umbrellas offer shade over the water, while palm trees and shrubs add to the tropical atmosphere. Clear blue skies with scattered clouds complete the scene.

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.

Guest favorite

Cottage in Saint Thomas

4.9 out of 5 average rating, 20 reviews

Island Breeze Cottage

Experience tranquillity and convenience at Island Breeze Cottage in Saint Thomas! Enjoy the serene ambience. Conveniently located 10 minutes to Charlotte Amalie, about 20 minutes to Magens Bay, and 13 minutes to Red Hook, by car. This cottage offers the perfect blend of relaxation and accessibility for your St. Thomas getaway. Be sure to keep a lookout for the Iguanas, but please do not feed them.

Superhost

Home in Southside

4.78 out of 5 average rating, 49 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.