Villa holiday rentals in Southside

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Popular amenities for villa rentals in Southside

Luxury villa rentals

Top guest favourite
Villa in East End
4.96 out of 5 average rating, 50 reviews

Tropical Palm Villa- Ocean Views From All Rooms!

TravisRating, 5 stars3 months ago
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.
Superhost
Villa in Saint Thomas
5 out of 5 average rating, 18 reviews

Paradise with Exquisite Ocean View

CathyRating, 5 stars1 month ago
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!
Top guest favourite
Villa in Saint Thomas
5 out of 5 average rating, 20 reviews

Villa Paradis! Spacious Home~Amazing Views & Pool!

KrystleRating, 5 stars1 month ago
What a wonderful stay! Amazing all around, from the villa's accommodations to the view! Just Wow!!!! Thank you Xaverie and Stephanie.
Guest favourite
Villa in Anna's Retreat
4.97 out of 5 average rating, 69 reviews

Good Vibes Only Ocean Villa-Private Pool-Views!

ReneRating, 5 stars1 month ago
We had a wonderful time at St. Thomas! Our first few days on the island we stayed with a friend that lives on the island. That was helpful, as the driving and roads are different then where we are from. I would suggest clicking on the directions on the Airbnb app to get the the house and use google maps. The house itself was more then we expected! The view from the back side of the house is directly to the ocean for miles and miles beautiful would be an understatement! Very spacious and we loved the layout! Our teenage boys had their own area and absolutely enjoyed relaxing in the pool! Two of the suites had a mini kitchen, perfect if you want a late night snack and do not wish to disturb anyone else they also had a private balcony, so peacful to hear the waves at night! There were also alot of little things that came with the house, play pens, box fans, bug spray, sunscreen etc. It was almost like we were at home! Roxanne was quick to respond with answers to any questions! Five ⭐️s!
Guest favourite
Villa in Northside
4.83 out of 5 average rating, 48 reviews

Minutes to Magens Bay - POOL - Views - Dining

JasonRating, 5 stars1 week ago
The view is amazing, plenty of room and very spacious. AWD is a must for the driveway, pool are is very nice. No complaints at all. We loved our week here !!!!
Top guest favourite
Villa in Charlotte Amalie
4.99 out of 5 average rating, 81 reviews

Tropical Modern Loft | SoHo Style | Concierge

LevyRating, 5 stars1 week ago
Zack was an excellent host. Very responsive and proactive communicator with suggestions for restaurants, etc. I can't say enough great things about his place itself. It's an incredibly hip and modern vibe and in a great walkable location to shopping and restaurants. VERY unique. We loved it. Centrally located on the island and he connected us with someone to rent a jeep. He made it so easy. The whole experience was great! We would definitely stay here again and highly recommend his place to anyone staying in St. Thomas!
Superhost
Villa in Northside
5 out of 5 average rating, 7 reviews

Stunning 4 Bedroom with Private Pool & Ocean View

TatumRating, 5 stars2 months ago
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.
Guest favourite
Villa in Charlotte Amalie
5 out of 5 average rating, 66 reviews

Hilltop Paradise Vacation Package with Jeep

MosesRating, 5 stars1 month ago
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!

Villa rentals with a pool

Guest favourite
Villa in East End
5 out of 5 average rating, 10 reviews

It’s an IRIE life

LoriRating, 5 stars3 weeks ago
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!!
Guest favourite
Villa in East End
4.97 out of 5 average rating, 29 reviews

Villa - Private Pool!

melanieRating, 5 stars2 weeks ago
This place was even better than described. Anything you could think of or might need was available to use. Peaceful, private and clean. One of the best places I’ve ever stayed! We would definitely book with this host in the future. Thank you 😊
Superhost
Villa in St. Thomas
4.79 out of 5 average rating, 58 reviews

Escape Ordinary: Villa Calvo

BonitaRating, 5 stars1 month ago
Enjoyed our stay. Wished it was a little warmer in the pools and definitely wanted a hot tub! But yes we enjoyed our stay!
Superhost
Villa in Water Island
5 out of 5 average rating, 5 reviews

Seagrape Villa on Water Island

CodyRating, 5 stars3 months ago
From start to finish, April made our stay one of our most memorable vacations. Having visited the island multiple times, we knew exactly what we wanted—and this property checked all the boxes. Anything we needed or requested was promptly addressed by either April or her property managers. This property is truly one of a kind, offering both stunning sunrise and sunset views. The ocean breeze is strong but refreshing, keeping you cool throughout the day. We also opted to have April provision our groceries, and she went above and beyond—everything was neatly put away upon our arrival. Water Island has always held a special place in our family’s heart, and staying here made it even more unforgettable. We can’t recommend it enough!
Guest favourite
Villa in East End
4.89 out of 5 average rating, 322 reviews

Romantic Villa with Private Pool - Rave Reviews!

JillRating, 5 stars3 weeks ago
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!!
Superhost
Villa in East End

Cottage at Oceanfront Villa with Pool

KatyaRating, 5 stars3 months ago
We absolutely loved our stay here. Beautiful property with quite a nice sized pool. Gorgeous view from the balcony, the sound of the ocean waves, so peaceful, it makes it hard to leave to explore the rest of the island. Beach is just a short walk from the villa with two restaurants. Very short ride to Red Hook Ferry and it’s surrounding shops and restaurants. The apartment itself and the villa are very clean and tastefully decorated, bed was comfortable. The little kitchen has everything you need to cook a simple meal. Hosts were a breeze to communicate with, very responsive and pleasant. Definitely One of the best airbnbs I’ve stayed in, highly recommend!
Superhost
Villa in East End
4.75 out of 5 average rating, 8 reviews

New Sea Glass Villa

SavannahRating, 5 stars1 month ago
Beautiful location and great place to say! Hosts were super helpful and responsive. Would definitely recommend and stay again!
Villa in East End
4.8 out of 5 average rating, 240 reviews

Private Pool Romantic Villa. Walk 2 Sapphire Beach

RobinRating, 5 stars1 month ago
We had such an amazing week staying here. The place was perfect for a couple, cute, clean, amazing pool right outside, super comfy bed, nice and cool AC, and just a 5 minute walk to arguably the most beautiful beach on the island (Sapphire). Red Hook is only a 5 minute drive (I’d rent a car unless you want to deal with taxis, walking on those roads is a bit sketchy). Red Hook is an awesome little community, great food, awesome boat excursions through Ocean Surfari (highly recommend!) and fun bars. We loved it here!

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