Pet-friendly holiday rentals in Northside

Save $1000/Wk! Haagensen House w/ Generator

A rare downtown estate located at the top of the famous “99 Steps”. Haagensen House is intimately tucked into the hillside of the stately neighborhood of Government Hill. Enjoy an easy walk to almost everything from this centrally located private estate and gardens with amazing harbor views. Parking is steps away to drive to our amazing beaches or take a leisurely 5 minute stroll downtown to the waterfront or enjoy world class dining, shopping and parks. Rental car is optional, so save $1000!

The Caribbean Farmhouse/Ocean Views, Solar Power

Welcome to your St. Thomas Northside retreat! This tropical side of the island offers breathtaking views of the world-famous Magens Bay. Located 5 minutes to Hull Bay & 10 minutes to Magens Bay. Enjoy privacy surrounded by lush landscaping. Solar power & generator on property to never lose power! The outdoor space features a private pool and backyard. Spend evenings watching stunning sunsets with breathtaking views, this property is perfect for unforgettable vacations with family or friends!

Tropical Modern Loft | SoHo Style | Concierge

Single night bookings welcome! A luxe art loft experience in the heart of St. Thomas, this exclusive space in a convenient central location provides a chic home base, with sleek design, concierge options, + creative vibes. Perfect for both adventure and serenity. Ample space to lounge, with a balanced historic/contemporary aesthetic, and near beaches, restaurants, historic landmarks, boutiques, + ferry/airport/transportation. Private gated parking and a cafe and art gallery right downstairs.

Bright Blue Retreat Studio+ Oversized Deck

Modern Studio, private entrance oversized Deck overlooking Buck and Water Island. Inside outside space. The studio is designed for outdoor lovers. The indoor has everything you need to eat sleep shower and be cool and happy to include a sleep number queen bed. Outdoors is where the fun is. Large 400sq foot deck with couch, picnic table all shaded and protected from rain. Centrally located on island: ✈️ 6 minutes from airport 🏖️5 minutes to the beach (Brewers Bay) or the University.

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.

Oceanfront | Peterborg | Infinity Pool | Generator

Welcome to Ciel Bleu, a luxury 4BR/4.5BA oceanfront villa on St. Thomas’s prestigious Peterborg Peninsula. This upscale retreat features designer interiors, a gourmet kitchen, and seamless indoor-outdoor living. Bedrooms offer A/C, en-suite baths, and private ocean-view terraces. The open-air great room embraces breezy island living. Outside, enjoy an infinity pool, sun decks, lounge areas, and BBQ—all set against panoramic sea views for an unforgettable Caribbean escape.

Villa Samadhi - Tailored time in paradise.

Enjoy sunrise and sunset overlooking Blackbeard's castle and the port of Charlotte Amalie. Relax in the pool taking in the Caribbean sun. Or cool off inside in the spacious open space of the villa. Get out for a 5 minute drive to Drake's seat to see the sailboats and recall the days of of exploration and pirates here. And 5 minutes later you arrive the famous Magen's Bay Beach. To tailor your time in paradise you arrange tours, catering and in Villa massage service.

Cozy Stylish Studio- Starlink-Solar-5 min to beach

Catch the island vibes in this charming studio apartment. Wake up to breathtaking views of the harbor! We are 10 min from the airport, 5 min from Hull Bay Beach and The Shack, and Moe’s Grocery is 1.5 miles down the road. Key features: • Cozy studio layout: Ideal for solo travelers or couples. • Queen-size bed: provides a comfortable sleeping setup • Private deck: Soak up the sun and panoramic views of the harbor! SOLAR POWERED STARLINK INTERNET

A Peace in Paradise too!

Cute 2/1 apartment on the quieter side of St. Thomas Located within walking distance to Hull Bay Beach. Split unit A/C’s located only in bedrooms. (However, you get a good breeze throughout the unit.) Also, we are completely family owned. We keep our prices low for guests that want to embrace the realness, history, culture, food, and stay humble all at the same time. So, if you’re looking for a resort or a hotel, this is not the spot for you.

Bellavista Grand Historic Villa | 6BR with Pool

Experience old-world charm in this stunning historic home overlooking downtown Charlotte Amalie. Once a beloved bed and breakfast, this spacious 6-bedroom, 5-bath sleeps 12 guests. Enjoy breathtaking harbor and city views, just a short walk to shops, restaurants, and the waterfront. Steps from the chic Pink Palm Hotel, where you can dine or relax by the pool- this home blends island history with modern comfort and unbeatable convenience!

Northside Retreat • Luxury, 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.

Large 1Br Hillside Ocean View Retreat

Unwind in a peaceful hillside retreat in St. Thomas with sweeping ocean and harbor views. This spacious 1BR/1.5BA features a bright living area, full kitchen, strong WiFi, and refreshing island breezes. Just 5 minutes to beaches, dining, airport, and downtown. Optional Jeep rental available for effortless exploring. Ideal for couples and longer stays. Pet-friendly—please clean up after your pet.