Villa holiday rentals in Southside

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Top-rated villa rentals in Southside

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Guest favourite

Villa in St. Thomas

4.82 out of 5 average rating, 250 reviews

Amazing Villa in Paradise: Views of 9 Islands

Take advantage of our great rates at one of the 10 BEST places to stay on St Thomas. I personally promise you will love it! Incredible views over 9 islands from everywhere! 50 steps from the pool. This villa has all new furniture, gorgeous new kitchen, remodeled bath, high end sheets and towels, beach towels, beach chairs, snorkel gear, a 42" TV, free WiFi and so much more. I provide a robust info packet with all the best beaches, restaurants, bars, grocery store and more. You will LOVE it!

Superhost

Villa in Water Island

5 out of 5 average rating, 5 reviews

Seagrape Villa on Water Island

Windswept Villa is a semi-attached condo situated on peaceful Water Island, USVI. This oceanfront property boasts two bedrooms, two bathrooms, and a beautiful cliffside setting. It offers an excellent opportunity for those who want to relax and escape civilization's hustle and bustle. You can enjoy breathtaking sunrises and sunsets from each balcony. Take a dip in the shared pool or take a short golf cart ride to Honeymoon Beach (golf cart included). Additional space is available upon request.

Guest favourite

Villa in Saint Thomas

4.93 out of 5 average rating, 130 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

Villa in Charlotte Amalie

4.99 out of 5 average rating, 89 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

Villa in St. Thomas

4.88 out of 5 average rating, 136 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

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.

Superhost

Villa in East End

4.85 out of 5 average rating, 27 reviews

4BR Hilltop vacation bliss! Incredible views!

Welcome to The Lazy Lizard, a stunning villa on the East End of St. Thomas. - 4 bedrooms and 3.5 baths with spacious, elegantly decorated interiors - Inviting living areas perfect for relaxation or entertaining - Expansive outdoor spaces featuring a private pool and multiple viewing decks - Nearly 360º views of the Caribbean Sea - Complimentary Concierge Service to enhance your stay - Just a 2-minute drive to Secret Harbor and 5 minutes to Red Hook -Automatic backup generator

Guest favourite

Villa in Anna's Retreat

4.97 out of 5 average rating, 71 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.

Guest favourite

Villa in Southside

4.95 out of 5 average rating, 66 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 favourite

Villa in Charlotte Amalie

5 out of 5 average rating, 70 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.

Guest favourite

Villa in Southside

5 out of 5 average rating, 11 reviews

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.

Guest favourite

Villa in Southside

4.94 out of 5 average rating, 16 reviews

Villa View Caribe

Welcome to Villa View Caribe! This stylish-newly renovated villa offers dramatic views and a quiet, comfortable yet refined decor that immediately invites you as the guest to relax and unwind. Once inside this tropical compound, you will immediately experience both a sense of awe at the expansive ocean views as you enter Villa View Caribe. The soaring ceilings encourage you to open your mind to fully experience your next Caribbean Adventure!