Holiday rentals with a pool in Northside

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.

VIEWS! Condo by Magen's Beach w/ POOL & generator!

Welcome to your retreat with panoramic ocean views located in Mahogany Run, 5 mins from Magen's Bay Beach. Enjoy spectacular views of the ocean from every room of the condo. This bright and airy condo 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

Chic 1 Bedroom Oasis with Designer Decor & Pool

Welcome to our impeccably designed oversized 1-bedroom apartment (+ queen size Murphy bed) a stylish retreat that promises an unforgettable stay in the heart of the historic district of Charlotte Amalie with its own plunge pool and deck. This apartment boasts a sophisticated ambiance, curated with the finest designer furnishings, decor and lighting as well as a custom kitchen. This is a perfect location to serve as the base to explore St. Thomas and the surrounding islands.

Ocean View Luxury Condo Near Magen's Bay Beach!

Our condo, situated in the private gated community of Mahogany Run, boasts stunning ocean views of several islands across both the US and British Virgin Islands. Relax by the community pool, or take a short 10-minute drive to Magen's Bay, which is ranked as one of the best beaches in the world. Our property provides a peaceful retreat while also being a short 15 to 20 minute drive away from most beaches, shops, bars, outdoor markets, and fine dining options on the island.

Sleek & Sunny Island Studio | Kitchenette

This unit is very small and cozy with great views of the seaports, airport, and downtown. Escape to your own oasis on the beautiful island of St. Tomas! This beautiful home features the following: *Pool *Free WiFi *Fully stocked kitchen *5 minutes to St. Thomas Airport *Coffee station *5-10 minutes from restaurants This unit is great for active solo adventurers or business travelers that are capable of using stairs. *This unit requires the use of stairs.*

Island View Retreat | Stunning Ocean Views!

Breathtaking ocean views from every room! This beautifully updated 2-bedroom, 2-bath condo in Mahogany Run features private balconies, stylish interiors, beach gear, in-unit laundry, and a fully stocked kitchen with modern appliances. Enjoy cool island breezes, a 5-minute walk to the community pool, and a short drive to Magens Bay. Backup generator for an extra piece of mind. Ideal for families or couples seeking peace, comfort, and an unforgettable island escape.

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.

Hilltop Paradise Vacation Package with Jeep

Start your next adventure and step into this brand new contemporary modern home hidden in the hills of St. Thomas. Here, you will be greeted with incredible, breathtaking views and an infinity pool overlooking the beautiful Charlotte Amalie. This carefully designed retreat sets the tone for a perfect adventure getaway for a group of friends/couples, or the perfect relaxation stop for a family. Whatever you choose, this home will not disappoint.

Villa Beso Del Sol-Three Bedroom Cozy Oasis

Villa Beso Del Sol is a three bedroom, three bath beach oasis nestled into the hills above the historic town of Charlotte Amalie. We are located in estate Solberg, once you arrive you may not want to leave, the pool is partially covered so you have the option of soaking in the shade or soaking in ALL the sun. Morning coffee or afternoon cocktails, the outdoor pool area is where you'll want to be your entire vacation.

Ocean View Retreat- 2BR/2BA Heated Pool, Generator

Escape to Sunrise Villas by Stacie, a private tropical mountaintop retreat in St. Thomas. Enjoy panoramic ocean views, a heated pool with Baja sun deck, jets, and lights, plus elegant indoor-outdoor living with 20-ft sliding doors, gourmet kitchen, bar, and fireplaces. With a whole-home generator, comfort is guaranteed. Perfect for couples, families, or friends—book the villa next door for up to 6 more guests.

2 Bed Condo w/Full Ocean Views & Guarded Community

Spectacular sunrises to memorable sunsets, Saltwater Dreams offers panoramic views of the British Virgin Islands and beyond. This spacious two bedroom, two bathroom condo offers two floors for ultimate privacy. A large living and dining area, full kitchen and an immense primary bedroom ensuite encompass the main level. Up a brief set of stairs, you will find the guest bedroom and second full bathroom.

Beautiful Mahogany Run Villa - Ocean view, Private

Stunning views at this huge, beautiful home in Mahogany Run! Grab views of Lovenlund bay and relax by your private pool in this stunning, Northside, house! Start your vacation off by sipping your favorite cocktail in the private pool! This beautiful home can accommodate ten people, making this spacious home a perfect location for a family or group of friends.