Vacation rentals in Southside

5 out of 5 average rating, 15 reviews

Home in Southside

Ocean View, Near Town, Backup Power/Strong Wifi

Brand new! Unwind in this stylish, tranquil retreat with breathtaking panoramic ocean views. Feel the Caribbean breeze as sailboats pass & the sun sets over the water. Enjoy sights of St. Croix, Puerto Rico, Water Island, and lush gardens. Minutes from Havensight & Charlotte Amalie, this private retreat features a deck, parking, and a pullout couch. Solar & battery-powered for uninterrupted comfort. Jeep rental available. Beach chairs, cooler, and concierge service included for a seamless stay!

4.95 out of 5 average rating, 131 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.

4.94 out of 5 average rating, 122 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.

Top guest favorite

Guesthouse in Southside

5 out of 5 average rating, 37 reviews

Darling Palms: Solar Tree House Studio

Solar powered, battery back up! Our spacious studio apartment is nestled among a paradise of palm trees, with a ‘tree house' atmosphere. Just a short stroll away, discover the allure of a nearby beach and resort, offering two restaurants, a market, and a pool bar for ultimate relaxation. Embrace the outdoor ambiance on our patio, complete with comfortable seating and a grill, perfect for alfresco dining. Please note that the studio shares a wall with another rental unit. Parking available!

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!

Top guest favorite

Apartment in Southside

5 out of 5 average rating, 54 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!

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.

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!

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.

5 out of 5 average rating, 7 reviews

Villa in Southside

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.

4.78 out of 5 average rating, 51 reviews

Home in Southside

Regatta Point! Ocean View Condo!

Regatta Point Villas is situated in a secured gated community in bolongo bay St. Thomas. Very spacious studio! Everything is brand new! Appliances etc…Very clean and comfortable! Newly renovated! You can see & hear the ocean from inside! Cable TV, Excellent WiFi. Close to Red hook (10 minutes) and downtown (15 minutes) Excellent location! Hot & Cold water in bathroom and kitchen.

Top guest favorite

5 out of 5 average rating, 32 reviews

Peaceful Oceanfront Oasis / Pool, Beach, Generator

Bring the whole family to the Caribbean in our brand new updated, waterfront, 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 & enjoy the comfort of our condo which is fully backed up by a new generator.

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Popular amenities for Southside vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Southside

5 out of 5 average rating, 4 reviews

Amazing Limetree Condo in Gorgeous St Thomas

MosheRating, 5 stars53 months ago

Joy is a great host. He responded very quickly, and was very helpful in finding the right place. The limetree resort is beautiful. Everything is newly redone. The staff of very nice and helpful. The beach is a bit rocky, But it’s the perfect spot to watch sunset! I definitely recommend this place.

5 out of 5 average rating, 4 reviews

Villa in Southside

Christmas Week at Marriott's Frenchman's Cove!

BethRating, 5 stars5 months ago

The apartment was beautiful. It had a great view and was close to the pool and ocean. I would definitely rent this place again.

4.9 out of 5 average rating, 30 reviews

Amazing views,touch the waves from the balcony !

GianaRating, 5 stars3 months ago

Anna was very responsive and accommodating. I would definitely recommend having a rental car because our taxi wanted to charge us more to drive up to the gate to get into the complex and it’s much easier than waiting for a taxi. Bring bug spray if you plan on sitting out on the balcony! Bring laundry detergent if you plan on using the washing machine. The condo was spotless and comfortable. Perfect for a couple night stay for two people! Views from the pool were picturesque!

4.95 out of 5 average rating, 64 reviews

Villa in Southside

Frenchman's View Villa 2 BD/2.5 BA w/ Pool

StephenRating, 5 stars1 month ago

I would absolutely recommend this place for anyone! Everything was as advertised the views were stunning the home was absolutely beautiful and sabrina was an excellent host. My favorite part was that it wasn't dead in the center of town nor was it too far away from Charlotte Amalie or anything else, really 10/10 on all fronts.

4.98 out of 5 average rating, 44 reviews

Beautiful Ocean Views/Amazing Sunsets/three pool!

KristianRating, 5 stars2 weeks ago

I absolutely loved my stay at Linda’s place. It was beautiful, peaceful, quiet, and well stocked of anything we might need. Everything looked exactly like the pictures. The view of the ocean from the balcony was amazing. We had a little trouble checking in due to the WiFi connection in the area, but I was able to get in contact with Linda and she helped us out right away. She also recommended some restaurants and places to check out in the area during our stay. The grocery store wasn’t too far away so that was also a plus. Would definitely recommend to anyone. Loved it ❤️.

4.5 out of 5 average rating, 4 reviews

Apartment in St. Thomas

Limetree Beach Resort 1 Bedroom

LarkRating, 5 stars27 months ago

Loved staying at Lime Tree! We stayed at 2 places in St. Thomas. This one, and one at Sapphire Beach. Lime Tree has a more secluded beach. It's small, but beautiful. If you're more into amazing view than getting in the ocean, this is great! There are some reefs around to snorkle (rent from the shop at the resort), but other than relaxing and eating, there's not much to do immediately around. The grounds were kept very clean. I would definitely stay here again for a lazy, relaxed retreat.

4.88 out of 5 average rating, 8 reviews

Apartment in Southside

Steve's Seaside Condo-2 Bedrooms-3 Pools

KellyRating, 5 stars3 weeks ago

Our stay was absolutely amazing! The condo was exactly what we were looking for to meet all our needs and make the trip great! The condo is within walking distance to Bolongo Bay beach resort which made our stay that much more convenient. From walking down the beach to grab coffee in the morning or a great dinner in the evening, it was the perfect location. The condo very clean, had beach gear for us to use, comfortable beds and couches, including enough seating for all of us on the patio to watch the beautiful sunsets and just relax. Emily thought of everything and her guestbook guide to local attractions was an added bonus for us. She was very responsive when we had questions and we would 100% stay at any of her places again.