Southside

Southside Hotels with Pools

Select your dates to see hotels in Southside with a Pools for a refreshing stay.

Scroll down to see hotels
Filter by:
Hotel Star Rating
≤2345
Guest Rating
Amazing 9+Great 8+Good 7+Pleasant 6+

Best Southside Hotels with Swimming Pools

Check out our selection of Southside hotels with Pools
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+
Hotels in Southside
Featured facilities: Bar, Spa, Massage Room
Very Good
101 reviews
8.3/10
1 night
From €234
Check Availability
68
Hotels in Southside
New Listing. St. Thomas Prime Oceanfront, Poolside, Remodeled 2BR/2BA Condo with Pullout – Ideal Bolongo Beach location with oceanside Dining options onsite (Mim's and Iggie's) and Generator. No Passport Needed for US Citizens to US Virgin Islands.Location, Location, Location! You've found your perfect home-base in America's tropical paradise. This on-island managed NON-SMOKING, OCEANFRONT 2BR/2BA, centrally located condo, offered for vacation rental by Island Time Properties VI, is situated in the best direct oceanfront villa #17, closest to quaint Bolongo Bay beach resort, and is walk-out level to the tranquil oceanfront pool at Watergate Villas, Bolongo beach in St. Thomas. Everything inside has been fully REMODELED with tropical décor, full kitchen with modern stainless-steel appliances, in-unit washer/dryer, (3) smart TVs in the living room and both bedrooms, nice bedding and linens, new bathrooms and furnishings, and a custom configured functional layout to maximize your comfort and enjoyment at this exquisite condo that enjoys year-round warm weather, island breezes and excellent oceanfront views of Bolongo Bay's tropical beauty and morning sunrises. Escape the crowds here with the comforts of home, and centrally located where you want to be to be close to everything St. Thomas offers. Additional to this beautiful condo, if you need additional accommodations for your traveling group, we also manage additional, closely located condos in this and the adjacent buildings onsite. Watergate Villas is equipped with a Generator for any power disruptions, which sets this property apart from many. You’ll find this two bedroom/two bathroom (2BR/2BA) condo with sofa pullout option to be an ideal accommodation for couples or families vacationing together. It’s the only one that has been completely remodeled. Condominium accommodates 4 persons perfectly (and up to 6 persons total) within a spacious 1100 sq feet, well-designed layout with two air-conditioned bedrooms set apart from each other to promote privacy, two bathrooms, and an air-conditioned kitchen/living area with a pull-out sofa option (small fee for the extra person(s)). The furnished 30’ ocean-facing patio is accessed directly via glass sliding doors that showcase breathtaking oceanfront views into the condo’s living/kitchen/dining room and from the master bedroom suite. In detail, the large oceanfront Master Bedroom suite is well appointed with a new King-size bed and matching furnishings, smart TV, air conditioning, ceiling fan, and en-suite Master Bathroom with tiled glass enclosed shower and brand new custom vanity and quartz countertop. The 2nd Guest Bedroom can be configured as two (2) single beds or together as a king-size bed to your preference (please advise at time of booking). The 2nd Bathroom is accessible by the Guest Bedroom or the Living Room and has a tub/shower combination and a separated vanity area to promote multiple people getting ready at the same time. The stackable Washer / Dryer is conveniently located within the condo on its central hallway for easy access by all. ***ALL LINENS, SHEETS, BATH/BEACH TOWELS & STARTER TOILETRIES ARE PROVIDED*** There is 1 parking pass provided for being able to park 1 car per condo***For those of you who may want to dine in and enjoy the spectacular views and privacy of your own villa, the condominium is equipped with a full kitchen with the appliances and cookware that you have at home (refrigerator, stove/oven, microwave, dishwasher, coffee maker, blender, etc). A dining area adjoins the living room with a large dining table and 6 chairs, in addition to patio/balcony seating for exterior oceanfront dining. You can also enjoy the two restaurants or do take-home dinners at your convenience.Escape the crowds here and enjoy the onsite amenities and this central island location as your home-base in America’s paradise.ONSITE: DINING & DIVING:2+ Restaurants onsite! MIM’s Seaside Bistro is directly oceanfront and serves surf and turf dinner nightly, located just beside the Watergate Villas pool. IGGIES OASIS is just a short seaside stroll to Bolongo Bay Beach Resort’s swim-up pool bar for food all throughout the day to enjoy oceanfront breakfast, lunch, happy hour, and dinner and cool tropical beverages, with some nights having live entertainment.Also onsite are St Thomas Diving Club (dive shop/boat for diving tours), and Heavenly Days catamaran day or sunset sails. CENTRAL LOCATION – CLOSE TO EVERYTHING:Condo's central location on the South sunny shore is right where you want to be - Close to everything! Charlotte Amalie and Havensight/Yacht Haven are a short 10 minutes drive west to the duty-free shopping capitol of the Caribbean, while Red Hook is only 8 minutes drive east, where you can take a person or car ferry to St. John, USVI via a short 15 minutes scenic Ferry ride. Being long-time residents here on island, we provide helpful suggestions for USVI activities and dining for planning the best vacation possible. A Rental Car is suggested for most convenience and affordability (especially for families), but taxis or limos can be coordinated in advance; noting there is no Uber of Lyft in the islands.Nearby within 5-20 minutes short drive are several grocery stores (Food Center, The Market, Cost-u-less, Moe's Markets, Kmart), pharmacies (Walgreens, Medicine Shoppe), Roy Schneider Hospital, and many beaches and attractions. BEACHES: To the North of the condo are Hull Bay and world famous Magen's Bay beaches. To the East of the condo are Secret Harbor, Lindqvist Beach, Sapphire and Coki Beaches (Coki beach being home to Coral World to swim with dolphins or sea lions). To the West of the condo on the South sunny shoreline are Limetree, Morningstar (Westin hotel) and Brewers Bay Beaches. EXCURSIONS: St Thomas has a myriad of activities and is a boating and fishing mecca with day boating trips to either swim/snorkel with Turtles or to eat pizza or tacos while floating in the beautiful ocean, and to powerboat or sail to nearby islands (St. John, Jost Van Dyke BVI for Soggy Dollar and Foxy’s popular beach bars, or The Baths in Virgin Gorda BVI), as well as deep-sea fishing charters.To recap, this memorable 2BR/2BA oceanfront condo is the perfect home base for your trip to St Thomas with everything you need for a comfortable stay and to be close to enjoying all St. Thomas has to offer and to do excursions to close-by islands. This spacious condo has plenty of room for guests to be extra comfortable with two (2) bedrooms with nice bedding and two (2) bathrooms featuring showers, tub and vanity areas to freshen up after a day of exploring. The living room sofa bed can be setup for extra comfort and convenience for sleeping up to a total of 6 persons. The close proximity of the condo to the tranquil pool, adjacent beach and restaurants will appeal to parents and children alike. From the pool, you are within footsteps of your condominium for cool refreshments. By staying at this condo in villa 17, there's no walking through the hot parking lot or many steps, as with a lot of the other units or other properties. If you have an infant, and bring your baby monitor, it may very well reach to the pool. You’ll feel right at home here ~ whether making your own favorite meals or simply relaxing in the open living/dining/kitchen areas or taking advantage of the Wi-Fi to stay connected or unwinding over coffee or a cocktail on the oceanfront patio that has a short walking path directly to the quaint oceanfront pool at Watergate Villas, Bolongo beach. This prime condo in oceanfront, poolside building 17 provides the best location on Bolongo Beach.Keywords: Condominium, Condo, oceanfront, 2BR, suite, St Thomas condo, vacation rental, St Thomas vacation rental, St Thomas vacation condo, Caribbean wedding condo; 2BR unit St Thomas, USVI condo, Virgin Island vacation, family condo St ThomasAbout pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.Extra setup/fee if more than 4p to use LR pullout.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 24.About events:No events allowed.
Amazing
3 reviews
9.4/10
Check Availability
99+
Hotels in Southside
Featured facilities: Public Beach, Bar, Fitness Room
Great
76 reviews
9.2/10
1 night
From €426
Check Availability
17
Hotels in Southside
Nothing but miles of crystal blue ocean... this 1bed/1ba oceanside gem is truly 'on the rocks' facing the beautiful Caribbean Sea. Perfect for a tropical getaway or a long-term work from home visit, you'll have all the comforts of home in a completely renovated unit tucked away from the hustle and bustle but just a short drive to downtown or the vibrant east end . All brand new appliances, including fast wifi, smart TV, dishwasher, w/d, new a/c units, brand new furniture, separate work desk and chair suitable for laptop/working remotely. Community pool.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 3-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Outstanding
12 reviews
9.8/10
Check Availability
37
Very Good
8.2/10
Check Availability
23
Hotels in Southside
Welcome to our FANTASTIC 2 bedroom - 2 bathroom oceanfront condo at Watergate Villas, Bolongo Bay, St. Thomas. When it comes to your vacation, as they say in real estate, it's location, location, location! As you can see from our pictures, this unit's prime location is almost like being on the balcony of a cruise ship. You are so close to the ocean you can toss a coconut from the balcony and hit the water. Take a look at the fabulous view from our patio. You will hear the waves every minute of every day. Our building's location directly adjacent to the pool deck is PERFECT for families with kids that like to spend LOTS of time at the pool. We are so close that our Wi Fi even works on the pool deck.You will love the convenience of our fully appointed kitchen if you like to make some of your own meals. For eating out, the island has countless restaurant options just a short drive away, but there are also 3 convenient oceanfront restaurants that are a short walk just down the beach. Mim's Seaside Bistro is located on the property and is more of an upscale dining experience open just for dinner. IGGIE'S beach bar is just 100 yards down the beach and every night they are sure to please with various live entertainment. You will also find The Lobster Grill, a little further down at Bolongo Beach Resort. I personally love going there for breakfast always a table oceanside. Also located at the resort are a PADI certified dive shop, water sports rentals, spa services and daily catamaran tours. Bolongo Bay has fantastic snorkeling right here without having to travel anywhere. The condo in total is roughly 1100 square feet and has a great layout with each bedroom having its own full bathroom with upgraded shower heads and great water pressure. The second bathroom can be utilized without having to go through the bedroom, which is a great privacy feature. Both bedrooms have A/C units with the living area having one as well. We have a high quality queen size Aerobed that can be set up in the living room to accommodate an additional 2 guests as needed, for a total of 6 guests total. The main living area, kitchen and master bedroom all have gorgeous views of the pool deck and ocean. Sitting on the huge patio listening to the waves just never gets old. Since the patio faces southeast, it gets shade at noon, so it is ideal temperature all afternoon long. The choices for nightlife on the island are many, but if you prefer staying in to rest a while we have a new 49” Smart TV which can also stream movies and shows with any subscriptions you may have. We have an active Netflix and Amazon Prime account to entertain you at the condo for those lazy nights in.Our front door is very convenient in proximity to the parking area and the laundry room is very close to your unit as well.Our unit is one of the most nicely appointed you will find in all of the Caribbean. We take great pride on having top quality mattresses and linens, ensuring a great NIGHT of rest, for the best vacation DAYS. We provide beach towels, beach chairs, snorkel equipment, beach toys, coolers, Bluetooth radio and much more. Most everything has been just newly replaced so it is all in great condition. This is our vacation home and we like things right. We spend 5-8 weeks per year here ourselves.The condo's location on the island is ideal. You will be less than a 15 minute drive from both of the primary towns on the island. Charlotte Amalie offers up a generous amount of culture with its abundance of historical buildings, shopping, restaurants and nightlife. Whatever it is you are looking for, you are sure to find it in Charlotte Amalie.The lively yachting hub of Red Hook is just a 10 minute drive east. This quaint little town will make you want visit the island again and again. You will find both locals and tourists enjoying everything from a great cocktail to a café latte. Red Hook is also the best place to take the ferry to St. John and the British Virgin Islands, which are just FABULOUS!I have so much more to tell you and would love the chance to speak more in depth about the many places I haven't mentioned. Please feel free to call me anytime, I am here to help you in any way I can. About pets:No pets allowed.About children:Children allowed: ages 0-17.About smoking:Smoking is not permitted.About events:No events allowed.
Outstanding
10/10
Check Availability
42
Hotels in Southside
Featured facilities: Private Swimming Pool
Outstanding
10/10
Check Availability
31
Hotels in Southside
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 20 minutes from the airport. Steps to the oceanside pool, beach, and seaside dining.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Adults only.About customRules:No Parties.Quiet hours 11PM to 7AM,All guests must be registered within the reservation.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Outstanding
6 reviews
10/10
Check Availability
70
Hotels in Southside
Remodeled, charming ocean view studio located within the quiet, safe Regatta Point Villas (25 min from airport), with private balcony overlooking Bolongo Bay. Minutes walk to: -Mim’s Seaside Bistro. Try its famous Lobster dish -Bolongo Bay Beach Resort: swim with sea turtles; snorkel; sunset cocktail cruise; sail to St. John, jet ski, snorkel, kayak -Iggies Restaurant & Bar, live music -The beach: part sand, part rocky but still provides tranquility. -1 queen bed w/ memory foam mattress. My unit has everything you need for a memorable stay. Regatta Point Villas are located on the 12 private acres of Coculus Point with panoramic views that include beautiful sunrises and sunsets, in Bolongo Bay in St. Thomas, U.S. Virgin Islands. Charlotte Amalie is a short 5 minute drive to the west. Red Hook & ferry service to St John & the British Virgin Islands is also only 8 minutes East End.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 13-17.Age 12 and older it is suitable for..About customRules:***Quiet time 10p-8a per condo association rules. Especially when on balcony please be mindful and respectful to fellow neighbors/owners.***.No loudness will be tolerated in complex and unit and will be subject to early termination of rental with no refund of remaining stay.,Only park in designated parking spot..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Outstanding
10 reviews
10/10
Check Availability
20
Hotels in Southside
Escape to Regatta’s Island Time Getaway for the Ultimate Waterfront experience! Look no further than this luxurious condo on St. Thomas! With stunning ocean views, crystal clear waters, and all the amenities you need, this rental is the perfect spot to escape and unwind. Located on a very safe private community, The condo features a fully equipped kitchen and more. Smart Tv, and Free wifi included in the Spacious living area, very comfortable furnishings, making it the perfect spot for a romantic retreat or a fun family vacation. Spend your days lounging by the pool, playing tennis, basketball, pickle ball, exploring the island with the best snorkeling or enjoying the local restaurants and bars. Mims Seaside Bistro and Iggies’ Oasis are within walking distance. Endless opportunities for adventure and relaxation, this waterfront oasis is the perfect vacation destination. Book your stay today and make some memories that will last forever while experiencing island living on St. Thomas USVI!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking allowed: in designated areas.About minBookingAge:Minimum age to rent: 23.About events:No events allowed.
Great
14 reviews
9.2/10
Check Availability
See All Hotels with Pools in Southside

Frequently Asked Questions

What's the best hotel with Swimming Pools in Southside?

What's the average price for hotels with Swimming Pools in Southside?

For hotels with Swimming Pools in Southside, the average price is €536 on weekdays and €568 on weekends (Friday–Saturday).

Which hotels with Swimming Pools in Southside have deals?

There are many deals available on Trip.com for both new and loyal users. Please check the promotions page to save your upcoming stays.

Southside Hotels with Pools Information

Total properties24
Number of reviews407
Weekday Avg. Price€536
Weekend Avg. Price€568