Villa holiday rentals in Southside

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Top-rated villa rentals in Southside

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Guest favourite

An aerial view of the Villa Royale displays the spacious layout of the property, featuring a blue roof and white exterior. The pool area is visible at the top, surrounded by lounge chairs, while landscaped grounds with pathways lead towards the entrance.

Villa in Southside

5 out of 5 average rating, 15 reviews

Villa Royale

Welcome to beautiful Villa Royale (formerly Villa La Creole)! Come indulge in the tranquility and comfort of this open-concept Villa. Tiled floors, high beamed ceilings, and filled with tasteful furnishings and decor. Enjoy the breathtaking views of the Caribbean Sea and relax to the sounds of crashing waves. Gaze at the colors that fill the sky at sunset. Unwind poolside and take a dip. The villa is located in Frenchman’s Bay close to shops and restaurants. Villa Royale, your serene getaway!

Top Guest favourite

A spacious deck offers stunning views of the ocean and surrounding islands during sunset. Comfortable seating is arranged for relaxation, with palm trees swaying gently in the breeze. The vibrant colors of the sky create a serene atmosphere perfect for unwinding.

Villa in St. Thomas

5 out of 5 average rating, 48 reviews

WOW Views! King Bd Studio w/Deck, AC,Pool,Gym,WIFI

Take a deep breath & enjoy EPIC views in our Spacious Comfortable Studio Cottage that command GRAND VIEWS. Count the many shades of BLUE & neighboring islands that circle the massive deck overlooking SPRING BAY. The salty ocean breeze, fluttering butterflies, swaying palms & majestic falcons will keep you mesmerized for hours. Or if you're adventurous, get lost star gazing at night w/ a nightcap & dose off in a hammock. Perfect Spot to UNWIND. Pool, Outdoor gym, on-site laundry, back up power.

Guest favourite

A serene beach scene features soft sand leading to clear turquoise waters. Smooth rocks delineate the shoreline, complemented by lush greenery in the background. A staircase ascends from the sand, providing access to the surrounding vibrant landscape and stunning coastal views.

Villa in Saint Thomas

4.92 out of 5 average rating, 136 reviews

Eau Claire- Magens Bay Affordable Beachfront Villa

Villa Eau Claire is a private gated affordable beachfront home directly on Magens Bay. Walk into the water at roughly half the price of any other waterfront home in the Virgin Islands. The property has 4 private individual villas each with breathtaking views of the bay. The Coral Studio is a 1 Bed/1 Bath villa located on a secluded beach in the world-famous Magens Bay. Guests will find the vibrant nightlife, charming boutiques, and fine dining restaurants just a few minutes away from home.

Top Guest favourite

The spacious living area features high vaulted ceilings, with ample natural light from large windows. A long dining table accommodates multiple guests, while a cozy seating area is arranged for relaxation. A decorative bookshelf filled with various books extends along one wall, enhancing the inviting atmosphere.

Villa in Charlotte Amalie

4.99 out of 5 average rating, 93 reviews

Tropical Modern Loft | SoHo Style | Concierge

Single night bookings welcome! A luxe art loft experience in the heart of St. Thomas, this exclusive space in a convenient central location provides a chic home base, with sleek design, concierge options, + creative vibes. Perfect for both adventure and serenity. Ample space to lounge, with a balanced historic/contemporary aesthetic, and near beaches, restaurants, historic landmarks, boutiques, + ferry/airport/transportation. Private gated parking and a cafe and art gallery right downstairs.

Guest favourite

The living room features vaulted ceilings with wooden beams, large windows providing views of the water, and comfortable seating arrangements. A neutral color palette is complemented by decorative plants and light fabrics. Natural light fills the space, enhancing the open layout.

Villa in Southside

4.93 out of 5 average rating, 121 reviews

Sunset Terrace | Epic Views, Pool & Family Fun!

Sunset Terrace offers panoramic views of the Caribbean Sea and surrounding islands from nearly every room. This fully air-conditioned villa features a private saltwater pool, four en-suite bedrooms, and spacious living and dining areas. . Relax on the covered patio, grill outdoors, or lounge poolside. Just a 5-minute drive to beaches, restaurants, and shopping. Perfect for families or groups, with kid-friendly amenities, backup generator, and concierge support for a seamless St. Thomas stay.

Guest favourite

A modern kitchen boasts sleek black and white cabinetry, with a large island at its center. Stools are arranged around the island, while large windows offer panoramic views of the mountains and water. Natural light fills the space, enhancing its contemporary design.

Villa in St. Thomas

4.87 out of 5 average rating, 141 reviews

NEW WATERFRONt Villa at Magens Bay, hot tub, Jeep

This new waterfront villa is conveniently located steps away from the Platform beach and 5 min. drive to famous Magens Bay Beach. Enjoy morning coffee watching turtles or Eagle rays flying above the turquoise water right from your balcony. This extraordinary furnishing and modern feel will provide cozy and exceptional vacation for your family and friends. The outdoor space offers great relaxing area overlooking the Caribbean sea. Hot tub brings the resort feel with the privacy you deserve.

Guest favourite

A private deck features two lounge chairs facing an expansive view of Charlotte Amalie, with the Caribbean Sea and distant hills visible. A round table sits between the chairs, providing a space for relaxation and enjoyment of the surrounding natural beauty.

Villa in Charlotte Amalie

5 out of 5 average rating, 38 reviews

The Ampersand Sky Villa: Iconic, Artful Luxury

The Ampersand Sky Villa: Established 1873, Reimagined 2021 Wake up fresh as morning dew after a heavenly night and step onto your expansive private deck overlooking city, sky, and sea. Leave the world behind while sipping freshly brewed espresso and watching ships cruise by. Beyond the gate, wander Charlotte Amalie's winding streets in pursuit of histories and mysteries of a complex past -- piracy, colonialism, the slave trade -- while discovering restaurants, bars, and other hidden gems.

Guest favourite

A panoramic view reveals vibrant turquoise waters and several nearby islands, bordered by lush greenery. The sky is partially filled with fluffy clouds, and the distant shoreline features contrasting structures amidst the natural landscape.

Villa in St. Thomas

4.83 out of 5 average rating, 263 reviews

Amazing Villa in Paradise: Views of 9 Islands

You will love this villa's amazing views, and perfect location on the East End of St Thomas. This villa has all new furniture, a gorgeous kitchen, remodeled bath, high end sheets and towels, beach towels, beach chairs, snorkel gear, a 42" TV, great WiFi and so much more. You are 50 steps from the pool and one of our on-site restaurants, plus 5 mins to 4 of the best beaches on island. I'll provide details on all the beaches, restaurants, bars, stores and more. You will absolutely love it!

Superhost

Villa in Southside

5 out of 5 average rating, 5 reviews

X-Mas Week at Marriott's Frenchman's Cove!

Don't miss out! This is a great way to spend the Holidays. From the Marriott's website: "Tucked along a picturesque hillside overlooking the calm azure waters of Pacquereau Bay...this luxurious resort is reminiscent of a quaint village surrounded by a secluded beach with amazing views of the Bay and St. Thomas harbor. Like the nearby historic town of Charlotte Amalie, the overall design reflects the Danish and British architectural influences set amidst a colorful tropical landscape."

Guest favourite

An aerial view of a modern villa showcases its spacious layout atop a rocky coastline. Solar panels are visible on the roof, surrounded by lush tropical vegetation. The property features a saltwater pool, patio areas, and close proximity to the ocean with crashing waves.

Villa in Anna's Retreat

4.98 out of 5 average rating, 80 reviews

Good Vibes Only Ocean Villa-Private Pool-Views!

Gorgeous Caribbean paradise w/ a salt water pool. Sleeping for 10 including 3 private bedrooms w/ensuite bathrooms. Sprawling living & fully stocked kitchen. Additional Queen sleepers in living & master + 1/2 bath. Enjoy stunning ocean views w/ direct line of site over to White Bay in the BVI, Tortola, Hans Lollik & Mandahl Beach/Salt Pond. The villa is equipped w/multiple patio areas & stunning pool w/ soothing trade-winds that blow through the property for comfortable outdoor living.

Superhost

A spacious outdoor lanai offers comfortable seating arranged around a coffee table, with vibrant cushion patterns. Beyond, a private pool reflects the expansive sky, showcasing views of distant islands and azure waters. Tall white pillars frame the area, creating a bright and open atmosphere.

Villa in St Thomas

5 out of 5 average rating, 13 reviews

Luxury Villa with Private Pool in St. Thomas

Welcome to Bella Vida, your private Caribbean oasis nestled in the heart of St. Thomas, Virgin Islands. - Artist-owned villa with personal artwork - Two spacious bedrooms with en-suite baths and AC - Large kitchen and elegant dining area - Private pool and covered lanai for outdoor dining - Stunning views of Charlotte Amalie Harbor and surrounding islands - Backup generator for uninterrupted comfort - Ample private parking - Washer and dryer for convenience

Guest favourite

An aerial view of a contemporary home reveals a red roof and an infinity pool lined with lounge chairs. Surrounding greenery enhances the sense of privacy, while a spacious driveway provides easy access. Large windows allow for plenty of natural light to enter the interior.

Villa in Charlotte Amalie

5 out of 5 average rating, 75 reviews

Hilltop Paradise Vacation Package with Jeep

Start your next adventure and step into this brand new contemporary modern home hidden in the hills of St. Thomas. Here, you will be greeted with incredible, breathtaking views and an infinity pool overlooking the beautiful Charlotte Amalie. This carefully designed retreat sets the tone for a perfect adventure getaway for a group of friends/couples, or the perfect relaxation stop for a family. Whatever you choose, this home will not disappoint.