Vacation rentals with a pool in Northside

5 out of 5 average rating, 42 reviews

An outdoor infinity pool offers serene views of the ocean and surrounding greenery. Four blue lounge chairs are positioned near the water's edge, providing a perfect spot for relaxation. Bright blue skies and distant islands complete the picturesque landscape.

Home in NorthSide

Heated Pool, OceanView, Generator, Local Discounts

Welcome to Sunrise Villas by Stacie! Enjoy island living at our newly constructed home offering breathtaking ocean/island views. Enjoy the heated pool with baja sun deck, bubblers/jets/lights. Relax in our spacious indoor/outdoor space with 20 foot sliding door, huge kitchen, bar, and fireplaces. No worries about island power with our whole home generator. Perfect escape for families with older children, couples, or a group of friends - book with our home right next door for up to 6 more guests!

Guesthouse in Saint Thomas

5 out of 5 average rating, 82 reviews

Sunrise Cottage - Secluded, Romantic, Private

Sunrise cottage is located on the cool & breezy north side of St. Thomas. A relaxing 1 bedroom cottage with a full kitchen & living area. You can soak up the sun on the sundeck or hang out in your private soaking pool, while appreciating the breath taking view during the day & the abundance of stars at night. When venturing out you are 20 mins to Magen’s Bay Beach, 15 mins to Town, 30 mins to Red Hook. Note: The hosts live on property with 2 dogs and this cottage is adult only 18 or older.

Guesthouse in Charlotte Amalie

An expansive deck overlooks scenic views of the ocean and nearby hills, featuring a refreshing pool and multiple lounge chairs. Lush greenery and decorative planters add a natural element to the inviting outdoor space.

4.86 out of 5 average rating, 59 reviews

Bellavista Cottage

The Bellavista Cottage is located on sunny St Thomas in the US Virgin Islands. We are pleased to offer charming and comfortable accommodations with access to the famous Bellavista Pool & Pool Deck. Situated above downtown Charlotte Amalie steeped in island history and architecture, the property is within walking distance of world class dining and shopping. Bellavista Cottage is an ideal off-the-beaten-path escape for savvy and discerning travelers seeking an intimate vacation experience.

4.92 out of 5 average rating, 144 reviews

Condo in Northside

VIEWS! Studio by Magen's Beach w/ POOL & Generator

Welcome to your remodeled ocean view studio located in Mahogany Run, just 5-mins from Magen's Bay Beach. Enjoy spectacular views of the ocean from the bed or seating area. This bright and airy studio is equipped with a plush king-size bed, a fully equipped kitchen, and a bathroom featuring a walk-in shower. Spend the days at one of the island's beaches, snorkeling, hanging out by the pool, or exploring downtown Charlotte Amalie. We HIGHLY recommend renting a car to get around the island.

Apartment in Saint Thomas

A serene pool area is framed by natural rock formations and tropical greenery. The clear water reflects the surrounding landscape, and a tiled border enhances the pool's inviting appearance. A wooden deck provides ample space for relaxation, creating a peaceful outdoor setting.

4.98 out of 5 average rating, 186 reviews

Hillside Hideaway

Perfect getaway for island romance, business, or solo adventuring. This well appointed one bedroom apartment is nestled in a quiet central hillside neighborhood with views of Hans Lollik, Jost Van Dyke, and Tortola islands. Conveniently located one mile from Magen's Bay and ten minutes to downtown Charlotte Amalie by car. Rental car is a must! Come enjoy the tranquil views, take a dip in the pool, and experience St. Thomas like a local. Please read all listing details and house rules.

A large swimming pool is surrounded by a sun deck featuring several lounge chairs. Lush tropical plants and trees provide a natural backdrop, while a well-maintained stone pathway leads down to the pool area. Bright sky and distant hills can be seen in the background.

4.94 out of 5 average rating, 52 reviews

Private Saltwater Poolside Cottage w/View and Gate

Come experience Jefe’s Poolside Oasis, nestled in the mountains with breathtaking views of the Caribbean Sea, Harbor, and Charlotte Amalie. You'll have your own guest house inside the Reel Paradise Estate, which feels like a tropical paradise. Step outside and take a dip in the pool just a few steps away, or lounge in the sun with a refreshing drink. The cozy living area has a comfortable seating area with an HD TV, a fully equipped kitchen, and a dining table for four.

4.95 out of 5 average rating, 105 reviews

Change Your Perspective at Villa Point of View

Change your perspective at Point of View villa, perched high above the historic town of Charlotte Amalie. Point of View is located within a gated community in Estate Mafolie. We are located mid island with an easy drive into town or to world famous Magens Bay. However, you may never want to leave the property once you see the sweeping harbor view. There are three bedrooms in the main house and separate fourth bedroom with a full kitchen on the lower pool level.

4.94 out of 5 average rating, 97 reviews

A serene pool area is depicted with a clear turquoise pool reflecting the sky. A graceful statue stands nearby, enhancing the tranquil setting. The distant view of the harbor is visible under a partly cloudy sky, framed by a decorative railing and outdoor seating.

Cottage in Northside

Caribia Cottage-Elegant Villa w/Private Pool

Caribia Cottage is located in a private Estate with access only through an electronic gate. The spectacular panoramic view of the St. Thomas Harbor is unforgettable and one which many a famous star toasted to when the property was formerly owned by a celebrated Broadway Producer. Walk just two steps from the Cottage into the spacious swimming pool. Enjoy gazing at the busiest Harbor in the Caribbean, as the mega yachts, seaplanes and cruise ships come and go.

A view of the spacious deck showcases a heated pool surrounded by lounge chairs and umbrellas. Steps lead down from the upper level, offering perspectives of the ocean and lush surroundings, while ambient lighting casts a warm glow over the area.

5 out of 5 average rating, 11 reviews

New! • Northside Retreat • Heated Pool • Generator

Discover the ultimate luxury retreat at The Villa Michelle. This exquisite property combines the charm of island living with modern comforts, offering an unparalleled vacation experience for up to seven guests. Need more room? The Poolside Villa is available (for an additional fee) that allows the property to accommodate up to thirteen guests. When not in use, it is blocked to ensure your full and exclusive use of the property.

4.87 out of 5 average rating, 39 reviews

The outdoor area features a private pool surrounded by a spacious sun deck, complete with lounge chairs. Nearby, a covered seating area invites relaxation, while lush tropical landscaping provides a serene backdrop against a clear blue sky.

Home in St. Thomas

High View Villa with Private Pool St. Thomas

Welcome to High View, your perfect getaway! - Stylish main level featuring spacious living and dining rooms with upgraded AC. - Private pool and sun deck with stunning views of Charlotte Amalie and the harbor. - Four luxurious bedrooms, each with air-conditioning and TVs. - Fully equipped lower-level guest suite for added privacy. - Conveniently located mid-island with easy access to local restaurants and attractions.

Superhost

A well-maintained pool area features a clear blue water pool surrounded by several lounge chairs. Lush greenery is evident in the background, while a wooden deck offers ample space for relaxation. The area is fenced, providing a sense of privacy.

4.94 out of 5 average rating, 33 reviews

Generator! Beautiful Virgin Island Triplex

This house is beautiful, and the pictures do not do it justice. The lush landscaping, amazing views, and sounds of nature all lend to the most relaxing Caribbean stay you can imagine. You can get to a beach within a 10-minute drive. Whole-home generator use is included!! This home is tucked into a great neighborhood near the highest point of the island, truly a getaway from the hustle and bustle.

Superhost

An indoor pool area is featured, surrounded by smooth flooring and large glass doors leading to an outdoor deck. The pool reflects light, highlighting its inviting blue water. Tropical plants and comfortable seating create a serene ambiance, with panoramic views of the sea visible beyond.