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Condo vacation rentals in Southside

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Top-rated condo rentals in Southside

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The living area features a spacious sofa and a patterned armchair arranged around a coffee table. Large sliding glass doors provide a view of the ocean and access to the balcony. A dining table with chairs is positioned near the window, allowing for bright natural light.

Condo in St. Thomas

4.96 out of 5 average rating, 146 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 15 minutes from the airport. Steps to the oceanside pool, beach, and seaside dining.

Top guest favorite

A beachfront view captures the clear turquoise waters lapping against a rocky shore. Lush palm trees sway gently in the foreground while various buildings line the beach. Rolling green hills rise in the background under a bright blue sky with scattered clouds.

Condo in Southside

4.94 out of 5 average rating, 125 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.

A serene seascape is visible, featuring gentle waves lapping at the shoreline under a colorful sky. Shades of pink and purple paint the horizon as clouds drift above distant islands, creating a peaceful and picturesque ocean view.

Condo in Southside

4.94 out of 5 average rating, 53 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!

A bright living area showcases large glass doors with stunning ocean views, allowing natural light to illuminate the space. Comfortable seating options include a light-colored sofa and cozy armchairs. A decorative plant stands beside a clean white end table, contributing to the airy atmosphere.

Condo in Southside

4.97 out of 5 average rating, 59 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

Top guest favorite

A bright living area features a comfortable teal sofa and a light coffee table, positioned on a vibrant floral rug. A large TV is mounted on a wooden cabinet, while a dining table with ocean views is visible through the sliding glass doors. Natural light illuminates the space.

Condo in St Thomas

4.94 out of 5 average rating, 49 reviews

*Generator* Ocean Front Sunsets, Next to Pool!

Welcome to Siren's Point! Beautifully remodeled 1BR/1BA condo with amazing views! Grab a cocktail and take in an island sunset while listening to the waves crash below your private balcony! Sea Cliff Villas, a gated community on the Southside, is centrally located between downtown Charlotte Amalie and Red Hook... Easy to get to all the best beaches, restaurants and shopping! Everything is ready for you to fall into island time! Three pools, tennis/pickleball and #OMGViews!

Top guest favorite

A bright living area features large windows revealing ocean views. Natural light fills the space, which includes a sofa, dining table with blue placemats, and decorative plants. A wall-mounted flat-screen TV adds to the modern appeal. The color palette emphasizes calming tones.

Condo in Southside

4.95 out of 5 average rating, 108 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. 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.

A well-lit bedroom features a spacious bed adorned with turquoise accents and decorative pillows. Sliding glass doors offer stunning views of the ocean and lead to a private balcony. Natural light enhances the room's serene atmosphere, complemented by a ceiling fan and tiled flooring.

Condo in Southside

4.88 out of 5 average rating, 25 reviews

A Ocean View in Paradise!

Welcome to our tranquil oasis at Regatta Point Villas! Experience modern elegance in our charming studio apartment with a plush KING-SIZE bed and FULL SLEEPER SOFA. Enjoy amenities like 3 pools, tennis/pickle ball court, and an ocean front restaurant all on property! Prepare your favorite meals in the well-appointed kitchenette! Dine al fresco on the charming balcony overlooking the shimmering ocean! Quick 15 min drive from the airport! Perfect for your next getaway!

A spacious bedroom features large glass doors opening to a balcony with ocean views. A king bed with a floral-patterned coverlet is complemented by bedside tables with lamps. Bright teal walls and ceiling fan provide a calming ambiance, while white tile flooring enhances the room's brightness.

Condo in Southside

4.91 out of 5 average rating, 11 reviews

2024 Remodel • W/D • King • Generator • Pickleball

Breathe in the Caribbean Sea breeze from your bedroom and watch yachts sail by! Welcome to your “Paradise View House!” Key Highlights: ☞ Newly Renovated (completed) ☞ Onsite Generator ☞ King Bed ☞ Fast Wifi & Office Desk ☞ Washer & Dryer in Unit ☞ 10 mins to Red Hook ☞ Parking Available ☞ Secure Gated Entrance ☞ Short Walk to Bolongo Beach ★ "To start Heidi was the most responsive airbnb host I’ve ever dealt with. From start to finish I felt valued and respected."

A dining area is presented with a marble-top table surrounded by brown chairs. A decorative bowl with fruit sits at the center, while large windows provide views of the ocean and greenery outside. Natural light fills the space through the glass doors leading to a balcony.

Condo in Southside

4.9 out of 5 average rating, 52 reviews

3 bed/3 bath, Ocean views, 3 Pools, Walk to Beach

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 three bedrooms that have king beds. Beautiful property with brand new tennis/basketball courts and access to 3 pools, and 2 restaurants. Back up generators for any island power outages.

A small round table with two white chairs is positioned on a balcony, overlooking the ocean. A bottle and two glasses are placed on the table, with a stunning sunset illuminating the sky in warm hues. Palm trees frame the view, creating a serene atmosphere.

Condo in St. Thomas

4.98 out of 5 average rating, 95 reviews

Oceanfront Villa: Stunning Sea Views, Pools, Gated

Experience serenity at Paradise Palm! Nestled in the gated Sea Cliff Villas, our condo offers breathtaking ocean views and a secluded yet central location right on the Caribbean Sea. Enjoy a clean, comfortable home with a stocked kitchen and bath, high-speed Wi-Fi, Smart TV, and a fabulous pool overlooking the sea. Beaches and dining are within walking distance, and nearby, you'll find exciting water sports and island activities. Your tropical escape awaits!

Top guest favorite

A balcony table is set for four, featuring white cups and a vase of flowers. Lush palm trees frame a serene view of the turquoise water, inviting a relaxing outdoor experience. The dining area offers a peaceful space to enjoy the natural surroundings.

Condo in Southside

5 out of 5 average rating, 47 reviews

Peaceful Oceanfront Oasis / Pool, Beach, Generator

Bring the whole family to the Caribbean in our brand new updated, oceanfront, two bedroom / two bathroom condo on the south side of beautiful St Thomas. Relaxing at Bolongo Bay beach or the pool is only steps away. Enjoy dining at the Caribbean restaurant on property, Mim’s Bistro, or in the condo with a full kitchen. Pickleball, tennis, and basketball courts available for use next door at Regatta point villas. The property is backed up by a new generator.

Natural light floods the open space from expansive glass windows, framing ocean views. A wooden ceiling adds warmth to the interior, while a staircase leads down to a casual dining area nearby. Clean lines and neutral tones create a serene atmosphere.

Condo in Southside

4.89 out of 5 average rating, 114 reviews

Sunshine Daydream - Our little piece of paradise!

Spend your days between at Sunshine Daydream with its beautiful ocean views. Rise up to paradise enjoying the gorgeous sunrises and sunsets from the private rooftop deck. This rental offers a fully equipped kitchen, 3 different pools, one of which is steps from the condo. There is easy beach access and we are centrally located between Charlotte Amalie and Red Hook. To top it off there are 2 restaurants and a bar within walking distance from the unit.

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Popular amenities for Southside condo rentals

Free parking on premises

Air conditioning

Weekly condo rentals

A tranquil pool area is framed by palm trees, with lounge chairs arranged around a clear blue pool. The ocean can be seen in the background, featuring gentle waves and a vibrant sky, enhancing the scenic coastal vista.

Condo in Southside

4.76 out of 5 average rating, 41 reviews

Ocean-Front 3 Bedroom Villa! Optional SUV Rental

A serene view of the Caribbean Sea stretching to the horizon, with gentle waves lapping against rocky shores. The sky is partially filled with scattered clouds, creating a bright and inviting atmosphere. Lush greenery frames the foreground, enhancing the natural beauty of the scene.

Condo in Southside

5 out of 5 average rating, 4 reviews

Blueviews @ Sea Cliff Pool, Beach, sunsets!

A vibrant landscape showcases a modern building adorned with blue accents. Lush palm trees frame the structure, which features spacious balconies. A well-maintained lawn leads up to the building, presenting a serene outdoor environment surrounded by tropical foliage.

Condo in Southside

5 out of 5 average rating, 3 reviews

Limetree Beach Resort Studio

A vibrant outdoor pool area is surrounded by palm trees and lounge chairs, offering views of the ocean. A white table with blue chairs and two umbrellas provide shaded seating. The water glistens under a clear blue sky, enhancing the inviting atmosphere.

Condo in St. Thomas

4.8 out of 5 average rating, 10 reviews

Tropical Paradise: Studio @ Limetree Resort

The living area features two light-colored sofas adorned with decorative pillows, complemented by a patterned area rug and a glass coffee table. A ceiling fan is visible above, and the kitchen can be seen in the background, characterized by light cabinetry and modern appliances.

Condo in Southside

5 out of 5 average rating, 7 reviews

New Listing! Island Bliss - 2 BR/3BD/2BTH

Top guest favorite

A private balcony overlooks the ocean, featuring a bottle of wine and a glass set against a vibrant sunset. The gentle waves can be seen lapping at the shoreline, with hints of orange and blue colors reflecting in the sky.

Condo in Southside

5 out of 5 average rating, 21 reviews

Ocean Serenity! Directly on the Water @Sea Cliff!

A private balcony features a round table set for two, complete with green placemats, glasses of red beverage, and plates. Framed by a railing, the view includes palm trees and a scenic coastline meeting the ocean under an open sky with scattered clouds.

Condo in St. Thomas

4.98 out of 5 average rating, 47 reviews

Beautiful Ocean Views/Amazing Sunsets/three pool!

A serene beach scene features soft sandy shores meeting calm turquoise waters. Lush green palm trees frame the coastline, while distant hills provide a gentle backdrop against a clear blue sky filled with scattered clouds.

Condo in St. Thomas

5 out of 5 average rating, 13 reviews

**Frenchmans Limetree St Thomas**

Pet-friendly condo rentals

A spacious great room is visible, featuring comfortable gray sofas and a wooden coffee table. Natural light filters through large sliding glass doors, connecting the indoor area to the covered balcony. A well-equipped kitchen and dining area are seen in the background, enhancing the open layout.

Condo in Cruz Bay

4.95 out of 5 average rating, 58 reviews

Villa w/ Pool, AC, 2 King BR, views, Back up power

A spacious pool area offers views of lush green hills and the harbor, with a blue sky and scattered clouds above. A single blue lounge chair is positioned by the pool, inviting relaxation and enjoyment of the picturesque landscape.

Condo in St. Thomas

5 out of 5 average rating, 3 reviews

Peace of Paradise Condo - Pool

A bright kitchen is shown with sleek white cabinetry and modern appliances. Natural light floods the space through sliding glass doors that open to a balcony with ocean views. A small dining area is visible, featuring a chair beside the window.

Condo in Southside

4.84 out of 5 average rating, 31 reviews

Amazing views,touch the waves from the balcony !

Condo in East End

4.83 out of 5 average rating, 134 reviews

Luxury 1/1 Oceanfront @ Sapphire Beach Resort

A vibrant view from the balcony showcases a lush landscape with bright red flowers in the foreground, contrasting with the turquoise waters of the Caribbean Sea. The scene includes gentle waves lapping at the sandy shoreline and distant green hills rising against a clear blue sky.

Condo in East End

4.77 out of 5 average rating, 115 reviews

Sapphire Beach Resort 1BR Family 1

A panoramic view is presented at sunset, showcasing a vibrant sky filled with hues of orange, pink, and purple. The silhouette of distant islands can be seen against the reflective water, creating a serene atmosphere.

Condo in Cruz Bay

4.81 out of 5 average rating, 140 reviews

Sunset Villa Studio Condo at The Hills Saint John

Top guest favorite

A scenic pathway leads from a stone staircase to a sandy beach, framed by swaying palm trees and lush greenery. The turquoise waters of Cowpet Bay are visible in the distance under a clear blue sky.

Condo in East End

5 out of 5 average rating, 36 reviews

Tropical Sands | Elysian Beach Resort | St. Thomas

A modern living area features a spacious gray sectional sofa adorned with blue accent pillows. Bright natural light filters through blinds, illuminating a stylish area rug. A flat-screen television is mounted on a contemporary media unit, with green potted plants adding a touch of greenery to the space.

Condo in East End

4.92 out of 5 average rating, 13 reviews

Exquisite Hillside Condo 3

Condo rentals with a pool

A refreshing swimming pool is visible with clear, blue water and a depth indicator of 4 feet. Sun loungers are placed nearby, and palm trees sway gently in the background, offering a glimpse of the ocean and a cloudy sky beyond.

Condo in Southside

4.98 out of 5 average rating, 60 reviews

Featured on HGTV! Sea Cliff Villa at Bolongo Bay

A serene coastal view is presented, featuring palm trees gently swaying in the breeze. The crystal blue ocean stretches out under a bright sky, with wispy clouds dotting the horizon. Rocky shoreline meets the water, enhancing the natural beauty of the scene.

Condo in Southside

4.91 out of 5 average rating, 22 reviews

On the Water! New Remodel! Amazing Views! 1BR/1BA

A serene beachfront view is presented, featuring calm waters reflecting pastel hues of the sunset. Lush palm trees frame the image, while distant islands are visible on the horizon. The coastal landscape offers a sense of tranquility and natural beauty.

Condo in Southside

4.77 out of 5 average rating, 124 reviews

Making Waves, hear the ocean from master bedroom

An illuminated infinity pool reflects the evening sky, framed by tall palm trees. lounge chairs line the pool area, and vibrant umbrellas provide shade. The resort building in the background incorporates tropical architecture, adding to the inviting ambiance of the outdoor space.

Condo in Southside

4.96 out of 5 average rating, 23 reviews

Marriott's Frenchman's Cove- 2 Bedroom 2 bath

A large outdoor swimming pool is framed by lush palm trees and vibrant blue umbrellas. Several lounge chairs are arranged around the pool, with a tranquil view of the ocean and bright sky in the background.

Condo in St. Thomas

Tropical Paradise: Studio @ Limetree Resort

The balcony view showcases Bolongo Bay, with gentle waves lapping against the shore. Lush greenery frames the scene, while distant hills and buildings are visible under a partly cloudy sky. The sun sets on the horizon, casting soft light over the water.

Condo in Southside

5 out of 5 average rating, 6 reviews

Make Good Waves~OCEAN VIEW

An outdoor area features a turquoise swimming pool surrounded by a wooden deck. Several lounge chairs are arranged for relaxation, with the ocean visible just beyond the railing. The serene water contrasts with the natural landscape and waves lapping at the rocks.

Condo in St. Thomas

4.92 out of 5 average rating, 24 reviews

1b/1ba New Deluxe Condo on the Ocean

A clear swimming pool reflects the surrounding palm trees and blue skies. Lounge chairs are arranged neatly around the pool area, offering ample space for relaxation. The condo building is visible in the background, showcasing a vibrant coastal design.

Condo in St Thomas

4.73 out of 5 average rating, 111 reviews

2 bedroom/2 bath oceanfront condo in Bolongo Bay

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