Holiday rentals with a pool in Southside

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Top-rated rentals with a pool in Southside

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Guest favourite

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 favourite

Condo in St. Thomas

4.95 out of 5 average rating, 129 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 favourite

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

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 favourite

Condo in Southside

4.96 out of 5 average rating, 51 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 favourite

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 favourite

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

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 favourite

Condo in Southside

4.92 out of 5 average rating, 106 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 favourite

Apartment in Southside

5 out of 5 average rating, 6 reviews

Steve's Seaside Condo-2 Bedrooms-3 Pools

This beautifully updated 2-bedroom condo at Regatta Point Villas in the USVI offers stunning ocean views and brand-new furnishings throughout. The primary bedroom features a king-size bed, while the second bedroom is perfect for families or groups with two queen beds. Enjoy resort-like amenities with 3-pools, tennis court, an on-site restaurant (Mim's Seaside Bistro) and easy access to nearby beaches and attractions. Ideal for relaxing getaways!

Superhost

Villa in Southside

5 out of 5 average rating, 5 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.

Guest favourite

Cottage in Saint Thomas

4.9 out of 5 average rating, 21 reviews

Island Breeze Cottage

Experience tranquillity and convenience at Island Breeze Cottage in Saint Thomas! Enjoy the serene ambience. Conveniently located 10 minutes to Charlotte Amalie, about 20 minutes to Magens Bay, and 13 minutes to Red Hook, by car. This cottage offers the perfect blend of relaxation and accessibility for your St. Thomas getaway. Be sure to keep a lookout for the Iguanas, but please do not feed them.