Discover

Oswego

Island

Bermuda

Oswego Island vacation home is set in a 3.2-acre private sanctuary in Bermuda, and designed by an award-winning architect. This exquisite retreat blends Bermuda's timeless charm with modern comforts, featuring an open-concept living space that offers breathtaking ocean views.

  • “The rental is amazing! Private island and doing the deal with Captain G for water taxis and day charters on the water makes it perfect. Captain G is the man and was an awesome tour guide! I’m definitely coming back. See you soon Captain!"

    ★★★★★

    - Justin,
    Airbnb Review

  • "This place is amazing and Geoffrey is awesome. Once in a lifetime experience. Although we may make it twice in a lifetime it was so much fun!"

    ★★★★★

    - Barry
    Airbnb Review

  • "Amazing experience! Stayed on Oswego Island with some friends. Captain G made the trip, he provided excellent water taxi service and fun adventures."

    ★★★★★

    - Matt Nicklin,
    Google Review

  • "Forget Disneyworld, Oswego Island is the most magical place on earth! An amazing spot to relax, recharge and reset. Just when you thought Bermuda couldn't be more beautiful, you find this place...."

    ★★★★★

    - Christy from Toronto,
    Oswego Guest

Bermudian Style
& Comfort

The beautifully designed Bermudian-style house is perfect for family vacations, romantic getaways, weddings, or corporate events. Accommodating 6-8 guests, it features three bedrooms and three bathrooms. Enjoy quality time in the spacious games room or prepare meals in the large open kitchen, complete with modern appliances and folding glass doors that open to a covered outdoor porch—ideal for al fresco dining.

Open concept kitchen with wooden beams and architect designed building
Private dock for mooring boats

Where You’ll Sleep

Bedroom One

Sleeps 2 People
King sized bed
Ensuite Bathroom

Bedroom Two

Sleeps 2 People
Queen sized bed

Bedroom Three

Sleeps 4 People
One Queen sized bed
Two Twin Beds

The house also features a pull out couch that can be used to accommodate bigger groups. View House Floor Plans for more details.

Upper Level I Lower Level I Gallery

Relax & Indulge with Luxury Amenities

    • Two docks for boats and swimming.

    • Deep water dock for boats up to 100ft. 150 amp shore power, running water and dock storage/shed are available.

    • 18 ft. power boat included in rental. (Operation and navigation lesson provided. Restrictions apply).

    • 6-person hot tub.

    • Kayaks and paddleboards.

    • Fire pit (wood provided).

    • Walking trails.

    • Boat shuttle or charter service available.

    • Bring your own provisions or request a stocked kitchen, catering or personal chef.

    • Open green space for events.

    • Gas BBQ for outdoor grilling.

    • Concierge services: Event + wedding planning, spa services, childcare.

    • Large wood burning fireplace (wood provided).

    • TV, DVD and surround system.

    • Books and games collection.

    • Ping pong table.

    • High-speed Wi-Fi.

    • Fully equipped kitchen.

    • Air Conditioning.

    • Washer, dryer and ironing board.

    • Hair dryer.

    • Towels, beach gear and bed linens.

    • Pet-friendly.

    • Long-term stays allowed.

    • Housekeeping is included at the end of your stay, or as needed for an additional fee.

  • We offer a range of personalized services, including:

    • Personal chef

    • Personal training

    • Spa services

    • Yoga sessions

    • Errand running

    • Boat charter & tours

    • Childcare

    • Wedding/event planning

    To ensure a smooth experience, please contact us via email at least 72 hours before your arrival to request any services.

Activities

  • Boat charters and island tours

    Charters + Island Tours

    Join Captain Geoffrey on the Honey Badger Express for an unforgettable adventure in Bermuda's beautiful turquoise waters. Customize your boat trip with options like eco-experiences, visits to the historic UNESCO World Heritage site of St. George, or a scenic sunset tour, all featuring food and beverage service. Learn more.


  • Local Bermuda Attractions and Activities

    Experience Bermuda

    This 21-square-mile island offers stunning sights, iconic pink-sand beaches, and a variety of outdoor adventures and sports, including seven world-class golf courses, tennis, pickleball, hiking, biking and so much more! Discover Bermuda's top attractions for a complete experience.

 

Getting Here

Getting to the island is easy and convenient. The most enjoyable way to travel to Oswego Island is an approximately 40-minute boat ride that brings you from the airport directly to the island. Taxi service and boat shuttle over to the island is also available. Whatever your preference is, our Guest Services team is here to help coordinate your travel and make any custom arrangements.
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