Vacation rentals in Southside

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Top-rated vacation rentals in Southside

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Guest favorite

Condo in St. Thomas

4.88 out of 5 average rating, 76 reviews

Your Piece of Paradise

Enjoy your home away from home in your comfortable condo centrally located on St Thomas within walking distance to Bolongo Bay Resort and Mimm’s Seafood Restaurant. Start your day off on your patio looking out at the turquoise water as you sip your breakfast beverage of choice before going to the multi-level pool or the beach with your own beach chairs/snorkel gear/towel. Then end the day on your KING Tempurpedic Mattress watching your favorite Netflix. This really is your "Piece of Paradise"!

Jan 4 – 11

$152 per night

Guest favorite

Condo in St. Thomas

4.97 out of 5 average rating, 96 reviews

Enjoy Sunsets at Fully Renovated Oceanfront Condo

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.

Sep 24 – Oct 1

$136 per night

Guest favorite

Condo in Southside

4.97 out of 5 average rating, 39 reviews

Three Little Sandpipers – Oceanfront!

Oceanfront! New remodel! This beautiful, 2-bedroom, 2-bath condo, “Three Little Sandpipers", is located in Watergate Villas in Bolongo Bay. It is steps away from beach, pool and restaurant/bar access. Bolongo Beach is walking distance and has excellent snorkeling and ocean rentals. Centrally-located 20 minutes from the airport and 10 minutes between Havensight and Redhook with many beaches and restaurants to choose from. Come relax and enjoy the breezy island right outside your front door!

Sep 27 – Oct 4

$309 per night

Superhost

Condo in Southside

4.93 out of 5 average rating, 106 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.

Nov 8 – 15

$119 per night

Superhost

Condo in Southside

4.96 out of 5 average rating, 28 reviews

Oceanfront penthouse oasis

You will smile as you wake up and 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. 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 explore ST. Gated community 3 pools & a short walk to the beach & two restaurants. Enjoy our paradise

Feb 25 – Mar 4

$449 per night

Guest favorite

Condo in Southside

4.96 out of 5 average rating, 24 reviews

"On the Rocks" Ocean Front 1BR/1BA Amazing Views!

Beautifully remodeled & stylishly furnished. 1BR/1BA condo w/amazing ocean & sunset views! "On the Rocks" is directly on the ocean w/an incredible ocean breeze. Hear the sound of the ocean waves crashing below as you enjoy sunset on your own private patio. Watch sailboats, ferries, and cruise ships pass by as you enjoy your favorite cocktail! This beautiful St. Thomas condo is centrally located in a gated community between Downtown Charlotte Amalie and Red Hook. The Perfect Location!

Jun 25 – Jul 2

$243 per night

Guest favorite

Condo in St. Thomas

4.97 out of 5 average rating, 39 reviews

Beautiful Ocean Views/Amazing Sunsets/three pool!

Relax in this beautifully designed, comfortable 1bdrm/1bath ocean view condo at Sea Cliff Villas. Comfortably furnished, spacious with modern décor, sofa bed and pack & play. Fully equipped kitchen w/private balcony only steps from the ocean! Watch the ships, boats, surfers & beautiful sunset from your balcony! Relax to the peaceful sounds of the ocean. Steps away from Iggie's and Mims restaurants & Bolongo Bay Beach. Access to 3 pools, tennis court, parking w/backup generator onsite.

Aug 2 – 9

$253 per night

Guest favorite

Apartment in Southside

5.0 out of 5 average rating, 21 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!

Jul 16 – 23

$218 per night

Superhost

Apartment in St. Thomas

4.88 out of 5 average rating, 128 reviews

"Cove Blanco" in St. Thomas

Freshly renovated and cozy, this one bedroom apartment is super comfortable and places you in a perfect spot between the country beaches and shopping hub of Charlotte Amalie. My place is close to the city center, shopping center, movie theater, 15 Minutes away from the world famous Magen's Bay & 15 minutes away from Main Street, Charlotte Amalie. My place is good for couples, solo adventurers, and business travelers. Back up generator on premises.

Sep 19 – 26

$103 per night

Guest favorite

Condo in St Thomas

4.93 out of 5 average rating, 30 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.

Feb 28 – Mar 7

$221 per night

Superhost

Condo in Southside

5.0 out of 5 average rating, 3 reviews

2BR condo -3 Pools, 2 restaurants and beach!

Step into "Almost Heaven," a stunning 2-bedroom, 2-bath condominium located at Watergate Villas on the southside of St. Thomas. This newly updated unit offers an exceptional waterfront lifestyle that provides a front-row seat to the breathtaking views of Bolongo Bay. The veranda, outfitted with comfortable outdoor furniture, is the perfect place to start your day with a coffee or wind down with a sunset cocktail.

Sep 15 – 22

$259 per night

Guest favorite

Condo in St. Thomas

4.92 out of 5 average rating, 73 reviews

Nala's Oceanview Play & Work Condo

This condo is spaciously comfortable, clean and stylishly decorated efficiency facing the bay at Regatta Point Villas. Located on a peninsula, providing an amazing view by day and night. A gated long and short term community on the southside of the island with convenient access to Bolongo beach, Mims Seaside Bistro, Iggies Beach Bar & Grill and other parts of the island.

Oct 8 – 15

$163 per night