Vacation rentals in Southside

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Top-rated vacation rentals in Southside

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Guest favorite

Guest suite in Southside

4.94 out of 5 average rating, 108 reviews

(Upper Level) Peaceful Getaway in Frenchman's Bay

Mosey along the exquisite upper level with patio oceanview, WiFi, AC, eco-friendly solar energy. Experience a spacious, calm location. Families, business guests, or group trips enjoy Bolongo Bay, Limetree, or Havensight all under a 5 min ride. Stay here for airport transfers, Westin conferences. Explore St. John, Honeymoon Beach on Water Island, and STT with an SUV rental. Click on our Group Villa listing, sleeps 15 guests for more space. Book here for 8 guests to feel comfortable on Rock City!

Guest favorite

Home in Southside

4.95 out of 5 average rating, 101 reviews

Sunset Terrace – Perfect home for your vacation!

Sunset Terrace Villa offers a private and accommodating home for your Caribbean vacation! This fully air-conditioned home offers a private pool, new renovations, furnishing and spectacular views of the water and surrounding islands. Beautiful sunsets are an everyday experience and can be enjoyed inside or from the covered, outdoor patio space. Centrally-located in a safe and scenic neighborhood. Nearest beach is only a 5 minute drive. Concierge service included. Designed by Ashley-Interiors

Guest favorite

Condo in Southside

4.99 out of 5 average rating, 78 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 and a queen sofa sleeper* **Rental unit avail next door for 2 more guests! Inquire within**

Guest favorite

Condo in Southside

4.9 out of 5 average rating, 30 reviews

Spacious Studio Unit With Amazing Sunrises

At Jack's Hideaway, you'll wake up to the most amazing sunrises from your private balcony. This very clean and comfortable unit is newly renovated and nicely furnished with all new appliances, fully equipped kitchen, Tempur-Pedic king size bed, sofa sleeper, towels & linens, WiFi, cable TV, ice maker, washer/dryer in unit, designated parking space. This rare, gated community is close to Bolongo Bay Beach Resort and Mim’s Bistro and a short drive to Red Hook, downtown, and numerous beaches.

Guest favorite

Condo in St. Thomas

4.97 out of 5 average rating, 112 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 20 minutes from the airport. Steps to the oceanside pool, beach, and seaside dining.

Superhost

Condo in St. Thomas

4.94 out of 5 average rating, 53 reviews

Villa Crystalia Newly renovated 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.

Guest favorite

Guesthouse in Southside

5 out of 5 average rating, 35 reviews

Darling Palms Tree House: Beachside Studio Oasis

Welcome to our spacious studio apartment nestled among a paradise of palm trees, with a ‘tree house' atmosphere. Just a short stroll away, discover the allure of a nearby beach and resort, offering two restaurants, a market, and a pool bar for ultimate relaxation. Embrace the outdoor ambiance on our expansive patio, complete with comfortable seating and a grill, perfect for alfresco dining. Please note that the studio shares a wall with another rental unit. Parking on property is available!

Guest favorite

Condo in Southside

4.94 out of 5 average rating, 115 reviews

Stay in style right on the ocean -Simply the BEST!

Take a look at the fabulous view from our unit, you will hear the waves every minute of every day. Your patio is so close to the ocean that you can actually throw a coconut and hit the water. I have done it! This is the PERFECT location for your stay in America's Tropical Paradise. We just finished updating this unit in April ‘21 with new kitchen tile, new fridge, new cookware, dishware and kitchen utensils, Smart TV. You will NOT find a nicer condo for this price anywhere on the island.

Guest favorite

Rental unit in St. Thomas

5 out of 5 average rating, 13 reviews

Stunning ocean-view suite with kitchen and balcony

Welcome to 24 Acres of secluded St. Thomas Bliss. Limetree is nestled on a secluded Caribbean beach at the southern end of the island, making this is an idyllic oceanside spot for couples and smaller families. Free of crowds and commercialized tourist areas, you'll find this resort offers a swim-up bar, tennis courts, fitness center and some of the best snorkeling you will do on the island; right on property. Well appointed and recently updated suites offer a beautiful view of the ocean.

Guest favorite

Condo in Southside

4.97 out of 5 average rating, 38 reviews

Oceanfront luxury penthouse

Fall asleep listening to the waves in our sunny & spacious 2-bedroom penthouse loft with 180-degree ocean views making it easy to let the sea breeze & natural sunlight fill the space. Gorgeous high-end furnishings, a fully-equipped kitchen, & plenty of comfortable spots to relax. Each bedroom has an ensuite bathroom - perfect place for couples or families wanting to relax and explore ST. Quiet gated community 3 pools & a short walk to the beach & two restaurants. Enjoy our paradise

Guest favorite

Rental unit in Southside

5 out of 5 average rating, 35 reviews

Newly Renovated Oceanfront Condo

Welcome to your perfect Caribbean island getaway! Meticulous planning and very careful thought have gone into this fully renovated oceanfront condo in the gated community of Sea Cliff Villas. Take a relaxing swim in one of the 3 gorgeous pools located within the community. You can take a short 2 minute walk to enjoy Bolongo Bay Beach, where you can swim, snorkel or just sit back and enjoy the beautiful view. This is your perfect opportunity to satisfy your taste for adventure!

Guest favorite

Guest suite in St. Thomas

4.84 out of 5 average rating, 87 reviews

The Artsy Studio for solo traveler's

The Artsy Studio is located at a Traditional Island House with a perfect ambiance at a lower hillside. Independent entrance for you alone at the main home in a secure safe upscale exclusive residential area surrounded by lush gardens and endless Light Blue Caribbean Seaviews. A short drive to the best shopping area and the Port of Havensight & Yacht Haven Grande Marina. Approximately 15 min. from the airport. Welcoming easy going Solo's for short stays !