
Villa vacation rentals in Southside
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Top-rated villa rentals in Southside
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Popular amenities for Southside villa rentals
Private villa rentals

Gorgeous Southern Cross and On the Rocks
We had a wonderful time at house . Great great porch , Trevor was very helpful it getting us to house . We did rent a car and it was great to get around town .

Gorgeous Pool Villa w/ Ocean view! 3 BD/3.5 BA
Beautiful home with beautiful views. It looked just like the pictures. Sabrina was extremely helpful with any questions we asked. We really enjoyed the pool area and outside patio. The house was only minutes away from shopping, restaurants, and many fun things to do. We would highly recommend this home to anyone interested in visiting the island.

New Year's Week at Marriott's Frenchman's Cove!
Everything was great. Very nice apartment, clean and well furnished. Nothing to complain about.

Groups! Unit B 3 BR/3.5Bath-Asta Cruise Villas!
This unit is in a great location! Restaurants, activities, grocery store and more were all within a short distance. The view was awesome. Communication was excellent with the host. I don’t have anything negative to say. Overall it was a great place to vacation!

Island Dream at Villa Sharazad - 4 Bedroom

Oceanview 2BR Villa | Marriott Frenchman's Cove
Luxury villa rentals

Tropical Palm Villa- Ocean Views From All Rooms!
We had an amazing week at the Tropical Palm Villa!! Spencer was extremely helpful and always quick to respond to any questions we had. Mason met us and made us feel right at home while checking us into the villa. The views from villa are incredible! The place was perfect for my family of five to enjoy St. Thomas and all it has to offer. We were especially grateful for the amenities that made cooking and grilling a breeze. We also enjoyed the beach gear that was provided, including chairs, beach umbrella, and snorkel gear. The location of the house is perfect, offering easy access to the beach, or a quick drive into Red Hook for restaurants, groceries, and the ferry to St. John. Overall, we had a tremendous week and hope to make it back soon.

Paradise with Exquisite Ocean View
I cannot say enough about how beautiful this house and location is. A beautiful view of the water in almost every location in the home. Very clean and the ere was plenty of room for 5 of us. We loved the spacious dining room with a huge dining table to seat a large group. When on the deck, you are almost directly above the water-feels like you are on a cruise ship! Andrew responded immediately whenever we had a question. I would definitely recommend this home!

Villa Paradis! Spacious Home~Amazing Views & Pool!
What a wonderful stay! Amazing all around, from the villa's accommodations to the view! Just Wow!!!! Thank you Xaverie and Stephanie.

Luxurious Villa with Stunning Ocean Views
Great location, privacy, and breathtaking views! The home was more space than we needed, but we enjoyed the open layout, and spacious bedrooms and bathrooms, and beautiful views from every room. We appreciated all of the amenities as well - from everything in the kitchen to the A/C units, ceiling fans, extra towels, laundry, etc. We loved the pool area with options for sitting in the sun and shade, and really enjoyed exploring the paths around the home and the “extra” deck and chairs. Great proximity to Magens Bay and our favorite spot, the Northside Grind for coffee, smoothies and sandwiches.

Minutes to Magens Bay - POOL - Views - Dining
This was the first time we visited STT. My children and grandchildren loved the home and pool. Safety was not a concern as it is in a gated community and the home is so comfortable with absolutely beautiful views. There is an apartment on lower level that was great for my son. There are a few steps to get to the top of main house but there is an elevator lift which we really appreciated. Great way to get baggage and groceries upstairs and used for baggage when checking out. This was a great addition that was well planned out by Cathy. We would definitely go back to this home, and it is just 2 miles from Megans Beach which you can see from the front porch. Thank you, Cathy, for your assistance in making our trip one we will always remember. Rob

Tropical Modern Loft | SoHo Style | Concierge
Wonderful place right in the heart of Charlotte Amalie. Easy walk to wonderful restaurants and shops. Zack arranged for our pick up from the airport and transportation to Chillout Charters in Red Hook after spending a few days at his amazing loft.

Hilltop Paradise Vacation Package with Jeep
We loved our stay at Hilltop Paradise! It was truly a paradise - the house is just as described and the views from the infinity pool are unbeatable. We had everything we needed, including super strong AC, all the kitchen gadgets, beach towels, shower amenities, and of course the gorgeous pool with custom color controls, which we had so much fun with during our night swims. We can’t understate how helpful the Jeep was as well. The car was ready to go the second we arrived and was incredibly helpful for our daily excursions out on the island. But the best part was meeting Rollito, the sweetest Airbnb dog that made our stay extra special while missing our own pups at home. Francis was always available to answer our questions and an amazing host. He’s really set up the perfect home away from home. We couldn’t have picked a better place to stay at St Thomas!

Sailfish Villa Luxury Beachfront 2BR on Magens Bay
You cannot go wrong booking on Magen’s Bay! The views are like none other… how often can you wake up in the morning to watching sea turtles, sting rays and iguanas from your balcony? Our family of five stayed in the main house for two nights to conclude our trip to the VIs. Things we loved: provided beach amenities (chairs, floats, coolers, towels…), pool table (we played with our three teenagers every night), huge rooms and bathrooms, big balcony, and most of all- access to the water with use of paddle boards and kayaks. Things that could use a little improvement: updated linens and a cleaner unit upon arrival (rug was visibly dirty, white couch had a seat stain, appliances in kitchen were visibly dirty). Even with these suggested improvements, this beautiful place deserves a 5 star! On top of that, our host was amazing! She communicated very well and was super helpful!! Very grateful that our family of five got to experience a stay on Magen’s Bay at Sailfish!! Thank you, Calisha!!
Villa rentals with a pool

It’s an IRIE life
Paige was a great host. Her place is exactly like the photos. Nice spot on the water. Quick walk to the beach and beach club to have breakfast lunch and/or dinner. We enjoyed our stay!!

Escape Ordinary: Villa Calvo
Enjoyed our stay. Wished it was a little warmer in the pools and definitely wanted a hot tub! But yes we enjoyed our stay!

Hibiscus Villa on Water Island
We loved EVERY minute of our stay here. Out your back door each morning you see a fantastic SUNRISE & out of the front balcony are breathtaking SUNSETS. Relaxing, safe, and very accommodating. They have the little things that you may have forgotten COVERED. We will be back…..Thank you for the great vacation!!!

Villa - Private Pool!
My husband and I really enjoyed our stay at Stephanie's condo! The private pool and deck and outdoor-ish shower were highlights and made for a truly unique experience! The location is great for getting to the downtown Red Hook area and the ferry to St John. The unit was clean and had everything we needed for our 5 night stay. Would gladly return!

JUICY Ocean Views, Massive Deck, 1 BRM, Pool, Gym
After being Double booked at another property, we found Jules! We are so happy we did and were thrilled! The property is beautiful! And the views are even better. We stayed in the Master Suite,the views were breathtaking as we looked on towards St John’s. The main town near by was “Red Hook” where there were so many options for restaurants and shops. Local beaches are just a short drive away. We will definitely be back.

Luxury Villa with Pool, steps from the Beach
Absolutely loved our stay at Fernando’s place in Saint Thomas! The location is simply perfect—stunning views and close to beautiful beaches. The accommodations were clean, comfortable, and well-equipped, making it feel like a home away from home. We enjoyed relaxing on the patio and taking in the breathtaking sunrises every morning. Overall, this was an unforgettable experience!

Romantic Villa with Private Pool - Rave Reviews!
Cheryls place is so nice. We loved the privacy of the place however close to so many beaches and restaurants. The pool was so nice, loved the garden shower and really everything. Would highly recommended her place in St Thomas!!

Stunning 4 Bedroom with Private Pool & Ocean View
Our family had a wonderful stay at this villa in Northside. The home was clean and everything was as described in the listing. The view from this home is unmatched! It was perfect for families that want their own space as the two upstairs bedrooms were on each side of the house. We did not sue the extra rooms during our stay but it would have been perfect if we needed it. The bedrooms, bathrooms, and pool were very clean. The kitchen was spacious and stocked with everything we needed. The Caribbean Retreats team were responsive and accommodating. We loved everything and really loved our stay! We would definitely rent this home again or recommend to others if we were to return to St. Thomas. Only a couple cons: 1) For families with little ones, the balcony is not entirely safe for them to run around. 2) The driveway is very difficult to pull out of with the incoming traffic up the mountain and it's difficult to turn your vehicle around in the driveway.
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- Flamenco Beach
- Honeymoon Beach
- Magens Bay Beach
- Limetree Beach
- Mosquito Bay Beach
- Oppenheimer Beach
- Coki Beach
- Cane Garden Beach
- Chocolate Hole
- Cinnamon Bay Beach
- Cane Bay Beach
- Peter Bay Beach
- Morningstar Beach
- Gibney Beach
- Pelican Cove Beach
- Josiah's Bay
- Playa Sun Bay
- Caneel Bay Beach
- Maho Bay Beach
- Playa el Convento
- Salt River Beach
- Grapetree Beach
- Oil Nut Bay
- Virgin Islands National Park
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