Holiday rentals with outdoor seating in Water Island

Ocean Nest #1

Welcome to our Caribbean paradise! Nestled among swaying palm trees and overlooking the turquoise waters, our newly renovated 4-BR home offers the ultimate tropical escape. The open-concept living area, comfortable seating and panoramic terrace views of the ocean creates the perfect setting for relaxing evenings with loved ones. Whether you're seeking a family vacation or a gathering of friends, Ocean Nest promises an unforgettable experience filled with comfort, adventure & endless memories.

Tropical Studio | Ocean Views | Pool | Bar | 244

Escape to paradise in this luxurious 1BR/1BA studio at Bluebeards Castle, with all the amenities you could want in the tropics! Safely perch above Frederiksberg Point, and minutes away from Yacht Haven, where the rich and famous (i.e. Jeff Bezos) stash yachts to replenish between islands. With a modern kitchenette, full refrigerator (with ice maker), oceans and city view balcony, resort pool, bar and restaurants, this luxury getaway is the ideal home base to experience St. Thomas like a local.

Island Times in Frenchtown, Centrally Located

We welcome you to the most authentic ISLAND TIMES vacation that we hope you fall in love with. Being on a hill, you will enjoy balmy breezes & beautiful views while appreciating the charm of Frenchtown. Wake up to the sun rising over the bay, spy the seaplane flying by your window, enjoy dinner on the patio with supplied amenities for cooking at home. Walk to bars, restaurants & downtown shopping; take a $1 Safari bus to the beach; pack lightly knowing that we have thought of everything for you!

Hidden in Havensight! Guest Favorite 2BD/2BA

Centrally located 2 BR/2 BA, “Hidden Jewel” accommodates your every need. You’ll be steps away from Havensight Mall area with great shopping, restaurants & more. A 2 min walk to Skyride Tramway, 7 min walk to Yacht Haven Grande & a mile away from downtown Charlotte Amalie. Most importantly, you’ll be at most a 20 min drive to beautiful beaches. Feeling adventurous? Take a 15 min drive to Red Hook where you have access to a 15 min ferry ride to St. John! Everything you need plus great weather!

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.

Villa Sunbeam. Rejuvenate & Relax w/ Ocean views.

Villa Sunbeam is located just outside the Havensight Area within walking distance to dining, attractions, & activities. This peaceful setting offers exceptional harbor views. With a polished new look, this carefully appointed, yet comfortable space, is perfect for remote working or a leisure getaway. Prince Rupert’s Cove, a beach, that is only a 2 minute walk down from the villa. Need more space for family or friends? A Private Space & Klarissas’s by the Sea are located just downstairs.

Fair Haven 2 bedroom

This stunning island retreat is located at 22 Havensight, just a three-minute drive from Havensight, where you’ll find a variety of dining options. Enjoy breathtaking ocean views and watch cruise ships as they dock. Fair Haven is the perfect destination for your next vacation, offering serene surroundings and unparalleled views. This immaculate two-bedroom apartment is for those looking for a relaxing getaway. This apartment creates a welcoming atmosphere from the moment you arrive.

Villa Isla B: Hotel style 1 bedroom 2-4 guests

Located on Water Island, This place is perfect or couples, friends and families! Located above Limestone Beach, you’ll be close to everything including the famous Honeymoon Beach, home to one of the best beach bars in the USVI: Dinghy’s Beach Bar! You’ll enjoy the sweeping views of St. Thomas, St. John and St. Croix on a private porch, full kitchen and bathroom, private entrance, tranquility of being off the main road, free Wi-Fi, A/C, and two full size beds. Get Cozy, Stay Awhile.

Mid-Century: Caribbean Style

Welcome to Shibusa (渋さ) at Shibui (渋い): A mid-century, Japanese pagoda residence in St. Thomas. Shibui was originally built in the 1960s as an award-winning luxury Japanese style resort: A colony of Japanese cottages, and a place for travellers to St. Thomas to enjoy a high-design experience. Now Shibui has transformed into a unique gated community of 26 historically preserved cottages—each with their own unique layout and view across the island.