Waterfront vacation rentals in Southside

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Top-rated waterfront rentals in Southside

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

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!

Jun 16 – 23

$465 per night

Guest favorite

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**

Dec 10 – 17

$143 per night

Guest favorite

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.

Feb 23 – Mar 2

$225 per night

Superhost

Condo in Southside

4.94 out of 5 average rating, 80 reviews

Sea Dreams at Regatta Point Villas

Regatta Point Villas is located in Bolongo Bay, St. Thomas. This spacious condo (2 full baths and 1 bedroom) features 1000sq.ft. of living space and is located steps away from the pool. It has beautiful ocean views from each room. Newly renovated unit. Bolongo beach is a short walk and has great snorkeling. 2 Tennis Courts, basketball hoop, and 3 pools are all accessible and steps away from the ocean. A short drive to Havensight and Redhook with many beaches and restaurants to choose from.

Aug 31 – Sep 7

$227 per night

Guest favorite

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.

Mar 22 – 29

$606 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.

Mar 7 – 14

$179 per night

Guest favorite

Home in Southside

5.0 out of 5 average rating, 5 reviews

Easy location, Ocean View, Tesla

This location is very centrally-located in St Thomas. Easy to find, yet Tucktaway. It has a full ocean view & wraparound deck. You will enjoy watching sailboats pass by & cruise ships dock. While watching the sunset, the sky will capture many colors by day & stars by night. The kitchen offers an open space leading to the living room. Easy for everyone to enjoy time together. Bedrooms open up to the pool deck & also have an ocean view. Powered by solar & Tesla to never lose power on vacation.

Jun 24 – Jul 1

$721 per night

Guest favorite

Condo in St. Thomas

4.98 out of 5 average rating, 40 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.

Sep 1 – 8

$249 per night

Guest favorite

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

Sep 25 – Oct 2

$449 per night

Guest favorite

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!

Dec 23 – 30

$312 per night

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 towels. Then end the day on your KING Tempurpedic Mattress watching your favorite Netflix. This really is your "Piece of Paradise"!

Apr 11 – 18

$149 per night

Guest favorite

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.

Apr 6 – 13

$224 per night