Holiday houses in Southside

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Top-rated holiday rentals in Southside

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Guest favourite

Villa in Southside

4.96 out of 5 average rating, 46 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!

25 July – 1 Aug

$5,923 AUD total

Guest favourite

Condo in Southside

4.99 out of 5 average rating, 74 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**

25 Aug – 1 Sept

$2,173 AUD total

Guest favourite

Condo in St. Thomas

4.97 out of 5 average rating, 97 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.

7 – 14 Aug

$2,586 AUD total

Guest favourite

Condo in Southside

4.95 out of 5 average rating, 22 reviews

Palm Vista - new 3 bedroom, 3 bath condo ocean

This incredibly spacious 3 bedroom/3 bathroom condo located at Sea Cliff Villas is newly renovated. Enjoy the 180-degree ocean view from the two gorgeous balconies! The fully equipped kitchen has bar seating and a large dining table. The condo comfortably sleeps 6 guests with two bedrooms that have king beds and one bedroom with a queen bed. Beautiful property with brand new tennis/basketball courts and access to 3 pools, and 2 restaurants. Back up generators for any island power outages.

13 – 20 Nov

$5,668 AUD total

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.

18 – 25 Nov

$2,158 AUD total

Guest favourite

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

17 – 24 Sept

$6,401 AUD total

Guest favourite

Condo in Southside

4.92 out of 5 average rating, 26 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!

18 – 25 Feb

$4,524 AUD total

Guest favourite

Apartment in Southside

5.0 out of 5 average rating, 22 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!

12 – 19 Oct

$2,919 AUD total

Guest favourite

Condo in St. Thomas

4.88 out of 5 average rating, 77 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 towels. Then end the day on your KING Tempurpedic Mattress watching your favorite Netflix. This really is your "Piece of Paradise"!

7 – 14 Oct

$2,107 AUD total

Guest favourite

Home in Southside

4.89 out of 5 average rating, 9 reviews

Central Location-Ocean View-Ask About Weekly Rate

Rare 2 Bedroom with minimal stairs! The beautiful views from the living room and bedroom will enhance your stay at this centrally-located, easily accessible condo. Active pickleball community - walk-ons welcome! Perfect for families as well as seniors, this well appointed-rental has access to three pools as well as the Bolongo Beach Resort where you can find the restaurants Mim's and Iggy's, within a short walking distance. Ask about long-term discounts!

8 – 15 Oct

$2,537 AUD total

Guest favourite

Condo in St Thomas

4.94 out of 5 average rating, 31 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.

18 – 25 Dec

$3,026 AUD total

Guest favourite

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.

9 – 16 Aug

$2,100 AUD total