Holiday rentals with outdoor seating in Southside

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!

Oceanfront w/ Balcony, Pool, Generator & Fast WiFi

🚨Oceanfront Flash Sale—Limited Dates Open🚨 Wake up to the sound of waves and enjoy coffee on your private balcony with stunning sea views. Rare opening at this updated condo with fast Wi-Fi, AC, full kitchen, and backup generator. 5–10 min to beaches, Red Hook dining, and ferries to St. John. Peaceful waterfront stay perfect for couples or remote work. This gap won’t last—book while discounted! All guests are welcome here—we’re proud to share our island home with guests from around the world.

(Upper Level) Peaceful Getaway in Frenchman Bay

Indulge in the serenity of our Rock City retreat, where breathtaking ocean views meet refined comfort. Enjoy the patio, WiFi, AC, and eco-friendly solar energy. Ideally situated for families and travelers alike, our haven is close to Morningstar Beach, Westin conferences, and Havensight shopping. For added convenience, rent an SUV or utilize taxi services. Click on our Group Villa listing which offers ample space for up to 15 guests. For a seamless stay, review listing details and house rules.

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.

Escape the Cold/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!

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

Oceanfront Sunrise Escape + Backup Power & 3 Pools

Welcome to your Caribbean oceanfront escape! This renovated condo was designed for the perfect island retreat, set in a secure gated community. Enjoy sunrise views and relax with a swim in one of three sparkling pools. In just two minutes you can stroll to Bolongo Bay Beach to snorkel, swim, or simply unwind by the sea. Whether you crave pure relaxation or a hint of adventure, this condo offers it all—complete with modern comforts, backup generator, and unforgettable island vibes.

Oceanfront Bliss & Perfect Sunsets + Backup Power

Our fully renovated 1BR/1BA condo is PERFECT for couples, small families or a friends getaway. Enjoy stunning ocean views and the sound of waves from every room or your private balcony. Watch breathtaking sunsets and cool off in one of three crystal-clear pools. Located in a gated community, just steps from the beach, oceanside pool, and seaside dining. Only 10 min to Red Hook (ferries to St. John & BVI) and Havensight, and 15 min from the airport—your perfect island escape! 🌴

*Generator* OceanFront Sunsets, Steps from 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 enjoy island time! Three pools, tennis/pickleball and #OMGViews!

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.

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.

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.