Oceanfront Beach house, Pool, Private Path to beach

Oceanfront Beach House! Escape to Rosebud, a breathtaking Caribbean retreat on Water Island. This luxurious hillside estate offers stunning ocean views, modern amenities, and the perfect blend of relaxation and adventure. Whether you’re lounging by the pool, exploring secluded beaches, or soaking in the island’s charm, Rosebud is your paradise. Stay, unwind, and make unforgettable memories!

There is also a private path leading directly to Limestone Beach, offering a secluded, peaceful spot for swimming and exploring. Just a short golf cart ride away, explore additional pristine beaches, hiking trails, and the laid-back charm of Water Island. Rosebud is designed for relaxation, adventure, and unforgettable island memories.

Sunrise & Afternoon Comfort:
The house is perfectly positioned to catch beautiful morning sunrises—ideal for starting your day with coffee and a view. In the afternoon, the home stays comfortably shaded, keeping things cool and relaxing after a day in the sun.

Work & Connectivity
Rosebud is equipped with a Tesla solar system, so you’ll never need to worry about electricity. Starlink Wi-Fi ensures you’ll always have fast, reliable internet, making it a great place to work remotely while enjoying the beauty of the island. Whether you’re catching up on emails or attending a virtual meeting, you’ll have the perfect environment to stay connected.

Guests have exclusive access to the main house, including all indoor and outdoor living spaces, the private pool, and terraces. There is an owner’s suite next door, which will typically be unoccupied during your stay. Self-check-in and check-out ensures a smooth and flexible arrival and departure. Enjoy your private island retreat!

We highly recommend renting a golf cart from Rachael’s Rentals to make getting around the island a breeze. While Honeymoon Beach and the ferry dock are just a quick 10-minute walk from our home, there’s so much more to see and do across the island. A golf cart makes it easy to explore at your own pace and is especially helpful when carrying beach gear, groceries or luggage. We suggest booking early, as inventory is limited and carts tend to go fast!

Although we are not typically on the island, we’ve built strong relationships with our island family and have plenty of local support to ensure you have everything you need during your stay. During our five years living on Water Island, we were deeply involved in the community—one of us even served as President of the Water Island Civic Association (WICA) for four of those years. Water Island’s charm lies in its welcoming community, where locals are always happy to share details about events like bingo, the Thursday night Wine Down, or the Monday afternoon social hour. You may even make lifelong friends!

We are here for you—don’t hesitate to reach out at any time with questions or needs. We are committed to responding promptly and ensuring your vacation is as enjoyable as possible. That said, please keep in mind that this is island life, and things don’t always go perfectly. Island time is real, and we kindly ask for your patience and understanding during your stay. Your comfort and happiness are our top priority, and we’re dedicated to making your experience unforgettable!

How to Get to Water Island

After arriving at Cyril E. King Airport (STT) in St. Thomas, take a short 5-minute taxi ride to Crown Bay Marina. From there, board the Water Island Ferry for a 10-minute ride to Phillips Landing. The last ferry is at 6pm, please consider this as part of your daily activities. On some days, there is a late 9pm ferry and there are options to book private water transportation. Tickets for the ferry can be purchased at the ferry boutique in Crown Bay Marina or directly on the ferry.

Upon arrival to Water Island, you'll see the island's post office and welcome center and if you've reserved a golf cart, someone from Rachael's Rentals will be waiting for you. From there, it is a quick 4-minute golf cart ride along the main road to bring you to Rosebud, 86 Estate Water Island.

Located on Water Island, the smallest of the four USVI islands at just 491.5 acres, Rosebud provides the perfect setting to disconnect and enjoy a laid-back, peaceful vacation. This charming residential island, with a population under 200, offers a tranquil retreat away from the hustle and bustle.

During your stay, you can enjoy a variety of activities, including:

Beach days with relaxation on the sand and swimming / snorkeling in crystal-clear waters.

Kayaking and exploring the shorelines of Water Island - rentals available at Dinghy's Beach Bar

Fishing or boating excursions to USVI or the BVI's - we are happy to recommend our favorites.

A day trip to St. Thomas or nearby St. John.

Hiking the island’s scenic paths and exploring historical military fortifications.

Enjoying movie nights on the beach with locals and fellow travelers.

Indulging in a leisurely lunch and cocktails at Honeymoon Beach.

What to Explore on Water Island

Honeymoon Beach – A pristine stretch of sand perfect for snorkeling, paddleboarding, sunbathing, or tossing a ball. You’ll frequently spot sea turtles and stingrays while snorkeling, and there’s a roped-off swim area for added safety. The beach also features beach tennis, pickleball and volleyball courts, plus several palapas offering shade.

Dinghy's Beach Bar & Grill – Located on Honeymoon Beach, this spot offers live music on Sundays, a Saturday evening movie on the beach, and a delicious menu of burgers, tacos, and cocktails. Check their social media page for other regular events. You can also rent beach chairs, umbrellas, kayaks, paddleboards, and snorkeling gear.

The Crossing Shaved Ice and Local Art – Situated off the main road, this lively stop is popular with locals. Enjoy shaved ice, play a game of cornhole, and shop for unique gifts from local Water Island artists. It’s a must-visit, where you can also grab bagged ice and cold beer.

Heidi's Hilltop Grill – Located up the hill from the beach, Heidi’s serves up the best fish tacos and amazing burgers, all while offering fantastic views. Enjoy cocktails, a Sunday brunch, and special events like Friday night dinners and Saturday afternoon bingo during the season.

WIMart – This charming container-turned-convenience store is open daily and stocks everything from basic groceries and condiments to drinks, toiletries, and more. It’s your go-to spot for all the essentials.

Limestone Beach – A beautiful bay right in front of Rosebud, with a private path leading you directly there. While this beach is rocky, it offers stunning views and refreshing breezes. On a calm day, you can snorkel and swim in the crystal-clear waters.

Fort Segarra - The U.S. Government acquired Water Island in 1944 to serve as a part of the coastal defense system for the U.S. Virgin Islands during World War II. The main fortification, Fort Segarra, located at the southern tip of the island, was constructed to protect the entrance to St. Thomas harbor. It consisted of two large gun emplacements, watchtowers, underground bunkers, and other military facilities. World War II ended before the two large guns could be installed.

Please note: Some attractions may have limited hours or close temporarily during the off-season, while others may only offer special events—like dinners or movie nights—during the high season. We recommend checking directly with each establishment for the most up-to-date information on availability and events.

A Sustainable Stay

As Water Island’s fresh water comes from rain collected in cisterns, we ask that you help conserve this valuable resource during your stay. Please take short showers, turn off the water while brushing your teeth, and be mindful of your water usage.

Note about Natural Debris:

A few times a year, typically after certain weather patterns, our beautiful southeastern-facing beach may experience some natural seaweed (sargassum) washing ashore. This is a normal and seasonal occurrence throughout the Caribbean and usually clears up quickly. It’s all part of the natural rhythm of island life—and the views are still stunning!

Rosebud isn’t just a place to stay—it’s a peaceful retreat, an island adventure, and a chance to unwind in one of the most beautiful spots in the Caribbean.