Villa vacation rentals in Southside

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Top-rated villa rentals in Southside

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Guest favorite

Villa in Charlotte Amalie

4.97 out of 5 average rating, 29 reviews

Tropical Modern Loft | SoHo Style | Concierge

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. Recently re-listed under new mgmt.

Guest favorite

Villa in Southside

4.96 out of 5 average rating, 56 reviews

Frenchman's View Villa 2 BD/2.5 BA w/ Pool

NEW LISTING! 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

Villa in East End

4.81 out of 5 average rating, 225 reviews

Private Pool Romantic Villa. Walk 2 Sapphire Beach

I fell in love w/ life on the island of perpetual summer. There's something special about having your own villa w/ a private pool. I also love the garden shower & the location. Pangea, the restaurant on site is phenomenal. The property is so close to my fave spots. Beautiful Sapphire Beach is in walking distance via a gate at the south end of the property. It boasts the Beach Buzz coffee & bfast spot, a Beach bar & grill w/ live music weekly, Paradise Pie pizza & SeaSalt fine dining restaurants.

Guest favorite

Villa in Anna's Retreat

5 out of 5 average rating, 53 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 and fully stocked kitchen. Additional Queen sleepers in living & master + 1/2 bath. Enjoy stunning ocean views with direct line of site over to White Bay in the BVI, Tortola, Hans Lollik and Mandahl Beach/Salt Pond. The villa is equipped with multiple patio areas & stunning pool w/ soothing trade-winds that blow through the property for comfortable outdoor living.

Guest favorite

Villa in Water Island

4.94 out of 5 average rating, 35 reviews

5 Star LUXE VACAY Designer Villa 38’POOL w BEACH!

LUX 3,000 sq. ft. BIG PRIVATE VILLA, HUGE POOL & only a 3 min walk to the BEACH! Want one of the finest beach homes in the Caribbean with all new furnishings? Our rates for six (6) are unbeatable!🥂🥂🥂 Our ‘bedrooms’ are VERY LARGE individual private suites with mahogany & coral en-suite bathrooms! Nothing compares to ‘Happy Hour in the comfort of a chic, newly furnished designer beach house, a huge 38’ infinity pool with a 60’ long gorgeous veranda—just steps from gorgeous Honeymoon Beach

Guest favorite

Villa in Northside

4.89 out of 5 average rating, 63 reviews

Sailfish Villa Beachfront Magens Bay St. Thomas!

Private beautiful Villa on the world's famous Magens Bay Beach. Enjoy swimming with Sea Turtles, Snorkeling & Kayaking on Magens Bay, just steps below Sailfish Villa with direct beach access. The property is a 4 Bed/4.5 Bath estate, a main house and two private detached cottages on the beach. Enjoy an amazing Outdoor Shower, Clear Kayak, Paddle Board and Stairs to the water! Sailfish Villa is located in the exclusive neighborhood of Peterborg, a short stroll along the shoreline to Magens Bay.

Superhost

Villa in Saint Thomas

4.92 out of 5 average rating, 117 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.

Guest favorite

Villa in St. Thomas

4.89 out of 5 average rating, 104 reviews

New Waterfront Villa on Magens bay, with 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 favorite

Villa in Charlotte Amalie

4.94 out of 5 average rating, 32 reviews

Salty Sway I - 2bed/2bath Beach House

Salty Sway I is a villa nestled on the coastline of Frenchman's Bay at the southern end of the island. The property has three private villas each with breathtaking ocean views. Salty Sway I is a 2 bed/2 bath unit with a kitchen, spacious living room, seaside balcony, and all the comforts of home. You'll love the property's private beach and offshore snorkeling. And the convenience of dining at the nearby Limetree Beach Club is great. Get the best of the Virgin Islands at Salty Sway Villas.

Guest favorite

Villa in Northside

5 out of 5 average rating, 15 reviews

Private Villa*MagensBay*Ocean views*Private Pool

Villa Del Mar is a luxury vacation rental villa offering two bedroom suites, luxurious great room, three dining areas and five private terraces. Our guests enjoy ocean views from every room including the pool and terraces. The villa sleeps up to four guests within two private suites with king beds, en-suite bath, walk in closets, individual A/C units & private terraces with unobstructed ocean views. Suite One's private outdoor double shower looking over the palm trees is dreamy.

Superhost

Villa in Northside

4.88 out of 5 average rating, 8 reviews

Newly remodeled 4br cliffside with dramatic views!

Enjoy a luxurious escape perched atop the majestic cliffs of Estate Peterborg! At Ruby Ridge, you will experience unparalleled views of the glorious Caribbean Sea as you take in the magnificence of this newly-renovated villa. Relax in the comfort and privacy of a one-of-a-kind getaway - there's no better place to escape the stresses of everyday life! Immerse yourself in the tranquility of paradise while taking advantage of the incredible panoramic views and aura of luxury.

Superhost

Villa in Southside

4.9 out of 5 average rating, 10 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!