Vacation rentals with a pool in Southside

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Top-rated rentals with a pool in Southside

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Top guest favorite

Apartment in Saint Thomas

5 out of 5 average rating, 21 reviews

Oceanview Studio Villa-Luxurious Infinity Pool-STT

EXQUISITE Location & Amenities! Look no further-reserve Morningstar Villa for your place in the sun in St Thomas, US Virgin Islands! This self-contained Studio is fully setup for your vacation with modern amenities and a luxurious infinity edge pool that overlooks beautiful Morningstar Beach. Offered by owners of Island Time Properties VI. No Passport needed for US Citizens. You will absolutely LOVE Morningstar Villa. The full kitchen, pool and proximity to Westin/Marriott resort is AMAZING!

Guest favorite

Home in Southside

4.91 out of 5 average rating, 11 reviews

Ocean, Sunsets, Great Location, Jeep Rental, Solar

Centrally located yet tucked away, this St. Thomas villa offers stunning ocean views from a wraparound deck. Watch sailboats pass by & cruise ships dock as the sky transforms with vibrant sunsets & starlit nights. The open-concept kitchen & living area create a bright, inviting space, while bedrooms open to the pool deck. Enjoy reliable solar power with backup batteries and two WiFi options. Private parking & Jeep rentals available. Boat charters & concierge offered for unforgettable adventures!

Guest favorite

An inviting ocean-side pool is surrounded by a spacious deck with several lounge chairs and tables. Clear blue water reflects the sunlight, while the vast ocean extends beyond the pool area, providing a stunning backdrop.

Condo in St. Thomas

4.95 out of 5 average rating, 130 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.

Guest favorite

Condo in Southside

4.94 out of 5 average rating, 121 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.

Superhost

A spacious pool area features two distinct swimming pools surrounded by lush greenery. Sun loungers are arranged nearby under large umbrellas. The scene is complemented by a bright sky, with sunlight reflecting off the water's surface.

Condo in Southside

4.88 out of 5 average rating, 77 reviews

Coral cove studio - ocean view

This apartment offers floor-to-ceiling views of the majestic Caribbean Sea from its south-facing windows. The studio has a full kitchen, a ocean faced balcony and a cozy beachy vibe. Enjoy the warmth of glorious sunrises and sunsets, watching the amazing cruise ships pass by right outside the windows. Enjoy one of the three pools, the tennis court or the beach within walking distance! Centrally located on the island. Easy to take a taxi only 10-15 minutes to downtown or to redhook!

Guest favorite

The image showcases a resort-style pool area featuring two interconnected pools surrounded by lush tropical greenery. Sun loungers provide areas for relaxation, while ocean views are visible in the background, highlighting the tranquil setting and inviting atmosphere.

Condo in Southside

4.96 out of 5 average rating, 52 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 serene outdoor seating area overlooks the ocean, featuring a glass table with two white cups on saucers. A small decorative vase with flowers adds a touch of charm. The horizon displays a soft sunset, enhancing the tranquil atmosphere.

Apartment in Southside

5 out of 5 average rating, 53 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

A clear blue pool is framed by palm trees and tropical plants, with sun loungers arranged around its perimeter. The expansive ocean view is visible in the background, under a vibrant sky. The surrounding patio is paved with natural stone.

Condo in Southside

4.95 out of 5 average rating, 101 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.

Superhost

A panoramic view showcases multiple pools surrounded by lush tropical landscaping and pathways. The blue sky stretches above, framing the serene ocean in the distance. Lounge chairs and umbrellas are visible, inviting relaxation in a tranquil outdoor space.

Condo in Southside

4.86 out of 5 average rating, 21 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!

Guest favorite

The image captures a serene view of a multi-level pool surrounded by lush greenery and palm trees. The expansive blue ocean glimmers in the background under a clear sky, while sun loungers are positioned around the pool, inviting relaxation.

Condo in Southside

4.93 out of 5 average rating, 107 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.

Guest favorite

A bright and airy great room features soaring ceilings and large windows that frame scenic views. Two comfortable sofas adorned with decorative cushions face a modern coffee table, while light reflects off the neutral walls. The open layout connects to a kitchen and dining area in the background.

Villa in Southside

4.93 out of 5 average rating, 14 reviews

Villa View Caribe

Welcome to Villa View Caribe! This stylish-newly renovated villa offers dramatic views and a quiet, comfortable yet refined decor that immediately invites you as the guest to relax and unwind. Once inside this tropical compound, you will immediately experience both a sense of awe at the expansive ocean views as you enter Villa View Caribe. The soaring ceilings encourage you to open your mind to fully experience your next Caribbean Adventure!

Guest favorite

An inviting pool area features a crystal-clear swimming pool surrounded by a spacious patio. Comfortable lounge chairs line the deck, offering a panoramic view of the Caribbean Sea and lush scenery in the background, creating a serene atmosphere.

Villa in Southside

5 out of 5 average rating, 6 reviews

NEW - open cal - Central Location - POOL Sleeps 9!

Private, island vibes and unbeatable convenience. Small Haven Villa is tucked into a secluded oceanfront perch, where the Caribbean stretches endlessly before you, waves rolling below, boats gliding across the horizon, yet you’re never far from the action. In just minutes, you can be savoring fresh seafood in Red Hook, catching the St. John ferry for a day of island-hopping, or browsing the shops and waterfront bars at Havensight.