Vacation rentals with a pool in Southside

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Top-rated rentals with a pool in Southside

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Villa in Southside

4.96 out of 5 average rating, 56 reviews

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

NEW LISTING! Breathtaking sunset and ocean views from this gorgeous villa nestled among the trees in paradise. A generous living space with oversized sectional effortlessly flows into the outdoor patio and pool area, perfect for sunbathing, a BBQ with friends and family, or a cocktail under the shaded cabana area. 2 fully air-conditioned bedrooms and 2.5 baths round out this fabulous property! Minutes to Havensight, Yacht Haven Grande, Charlotte Amalie, and a variety of shops and restaurants!

Guest favorite

Home in Southside

4.95 out of 5 average rating, 100 reviews

Sunset Terrace – Perfect home for your vacation!

Sunset Terrace Villa offers a private and accommodating home for your Caribbean vacation! This fully air-conditioned home offers a private pool, new renovations, furnishing and spectacular views of the water and surrounding islands. Beautiful sunsets are an everyday experience and can be enjoyed inside or from the covered, outdoor patio space. Centrally-located in a safe and scenic neighborhood. Nearest beach is only a 5 minute drive. Concierge service included. Designed by Ashley-Interiors

Guest favorite

Condo in Southside

4.99 out of 5 average rating, 78 reviews

Mermaid Hideaway

Charming ocean view studio located within the quiet, safe Regatta Point Villas (25 min from airport), with private balcony overlooking Bolongo Bay and panoramic views with sunrises and sunsets! Minutes walk to: -Mim’s Seaside Bistro -Bolongo Bay Beach Resort w/ catamaran cruises, kayak rentals, and more -Iggies Restaurant & Bar, live music -The beach: part sand, part rocky but still great! -*1 queen bed and a queen sofa sleeper* **Rental unit avail next door for 2 more guests! Inquire within**

Guest favorite

Condo in Southside

4.9 out of 5 average rating, 30 reviews

Spacious Studio Unit With Amazing Sunrises

At Jack's Hideaway, you'll wake up to the most amazing sunrises from your private balcony. This very clean and comfortable unit is newly renovated and nicely furnished with all new appliances, fully equipped kitchen, Tempur-Pedic king size bed, sofa sleeper, towels & linens, WiFi, cable TV, ice maker, washer/dryer in unit, designated parking space. This rare, gated community is close to Bolongo Bay Beach Resort and Mim’s Bistro and a short drive to Red Hook, downtown, and numerous beaches.

Guest favorite

Condo in St. Thomas

4.97 out of 5 average rating, 111 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 20 minutes from the airport. Steps to the oceanside pool, beach, and seaside dining.

Superhost

Condo in St. Thomas

4.94 out of 5 average rating, 53 reviews

Villa Crystalia Newly renovated Oceanside condo

Relax and take in the views and sounds of this brand new stunning seaside villa. Listen to the waves and watch the ship and boat traffic pass by your balcony. Centrally located, with Charlotte Amalie and Red hook only a quick ten minute drive. Enjoy pool and tennis courts on site with great restaurants close by. Villa is equipped with mini split AC’s and new appliances, including washer and dryer. All linens and towels provided. Beach chairs, a cooler and tennis rackets are available for use.

Guest favorite

Condo in Southside

4.88 out of 5 average rating, 25 reviews

Amazing views,touch the waves from the balcony !

This unique place has a style all its own. Newly renovated with full Kitchen and laundry. Situated right on the beach with beautiful views of the ocean and sunsets . Perfect for romantic get away for 2 , but can accommodate up to 2 children as well! Has 2 pools and tennis court , conveniently located , only 15 min from airport or 15 min to St. John ferry from Redhook. Attention: Our resort has fully automatic generator, that is very important on our island since electricity goes off a lot !

Guest favorite

Condo in Southside

4.94 out of 5 average rating, 114 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.

Guest favorite

Condo in Southside

4.97 out of 5 average rating, 38 reviews

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

Guest favorite

Condo in St Thomas

4.92 out of 5 average rating, 37 reviews

Ocean-Front Siren's Point, Steps from Pool!

Welcome to Siren's Point! Beautifully remodeled 1BR/1BA condo with amazing views! Grab a cocktail and watch the 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 relax and fall into island time! Three pools, tennis/pickleball and #OMGViews!

Guest favorite

Rental unit in Southside

5 out of 5 average rating, 35 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!

Guest favorite

Condo in St. Thomas

4.93 out of 5 average rating, 30 reviews

Sunset in Paradise

Let tranquillity wash over you in this freshly renovated and newly furnished sea side retreat. Once you arrive, you will never want to leave this paradise. Perfectly situated in a gated community with generators for your peace of mind. This spacious and relaxing condo has everything your heart desires: king size bed, La-Z-Boy queen size pullout couch, full kitchen, and a balcony that will make you feel like you’re sitting at the edge of the world.