Holiday rentals with a pool in Northside

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.

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.

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.

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.

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.

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.

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.

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.

PalmPoolVilla - Solar & Battery 4 bed 4 en-suite

Escape to paradise! Welcome to the Palm Pool Villa a spacious 4-bedroom and a common open living area that unveils a breathtaking panoramic sea views 🏝️ Forget your worries in this spacious and serene space. Tesla Power walls and Solar ensure power for your entire stay and Starlink wifi ensures you can stay connected while away.