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Bradley Circle #24

10 bedrooms·10.5 bathrooms·24 guests·7,200 sq/ft
Beach access
Views of the water
Pool

Perched along the pristine shoreline of Hilton Head's exclusive Singleton Beach, Bradley Circle #24 is an extraordinary 7,200-square-foot oceanfront estate designed for unforgettable group getaways. With 10 beautifully appointed bedrooms, 10 full and two half bathrooms, and accommodations for up to 24 guests, this luxurious retreat blends elegant coastal style with exceptional comfort. Expansive living spaces, soaring ceilings, and thoughtfully curated furnishings create an inviting atmosphere, while the gourmet kitchen, complete with premium appliances, generous island seating, and a spacious dining area, makes gathering effortless. A top-floor entertainment level featuring a second living area, full kitchen, bar, pool table, and game room provides endless opportunities to relax and celebrate, all complemented by sweeping ocean views from multiple covered balconies. Outside, an infinity pool with complimentary heating overlooks the beach, creating a private oasis for soaking up the Lowcountry sunshine. Lounge poolside, enjoy outdoor dining with the grill, or stroll down the private boardwalk for direct access to the sand and surf. Every bedroom features its own ensuite bathroom, with select suites offering private balconies and picturesque ocean views for an added touch of luxury. An office for remote work, a laundry room, and parking for up to five vehicles provide everyday convenience without compromising the experience. Just moments from championship golf courses, waterfront dining, scenic nature preserves, and the island's renowned beaches, Bradley Circle #24 offers an exceptional setting for family vacations, milestone celebrations, weddings, and corporate retreats on one of Hilton Head's most sought-after stretches of coastline.

Our promise

Satisfaction Guarantee

We've reviewed thousands of homes and approve only the best. Each one is professionally managed and vetted for comfort and style, raising the bar for every stay.

KEY Curation Notes

Beach access is direct and private via a boardwalk from the Singleton Beach frontage, offering ocean views, an infinity pool, and four covered balconies throughout the 7,200 sq. ft. estate. Multiple rooms face the water with unobstructed sight lines.
All 10 bedrooms feature private ensuite bathrooms, with many offering ocean-facing windows and balconies. The home sleeps 24 plus provides two additional trifold sleepers, configured with king beds, queen beds, and bunk rooms.
Fourth-floor entertainment space houses a full bar, kitchen, dining area, and game room with pool table, ping pong, foosball, and cornhole, all opening to covered balconies overlooking the ocean. The main-level gourmet kitchen has a five-burner gas stove, wine fridge, island seating for eight, and a formal dining table for twelve.
Private office space accommodates remote work or team planning, while two laundry rooms and six-vehicle parking handle logistics for large stays.
Ventilation comes via sliding doors and bathroom fans—casement windows are locked due to strong island wind patterns and $5,000 replacement costs. Pool heating costs $150/day and must be reserved 48 hours in advance (October through April only, 90°F maximum, weather-dependent below 50°F).

Amenities

Indoor
Basic cooking essentials
Dishes and silverware
Dishwasher
Drip coffee maker
Oven
Outdoor
Balcony
Deck
Outdoor seating
Outdoor dining
Sunloungers
Misc
WiFi
Cleaning supplies
Laundry detergent
Private entrance
Smartlock

Bedroom details

Bedroom 1: King
Bedroom 2: King
Bedroom 3: King
Bedroom 4: Single Over Single Bunk + Double
Bedroom 5: Single Over Single Bunk + Queen
Bedroom 6: King
Bedroom 7: King
Bedroom 8: King
Bedroom 9: King
Bedroom 10: King

Location

Inside the destination

Neighborhood: Singleton Beach - Shelter Cove Marina, Tanger Outlets, and the public tennis courts at Chaplin Park are all just minutes away, with the tennis courts only a two-minute bike ride from the property. - Hilton Head is a lowcountry gem that has a distinct cultural, scenic, and culinary presence. With unique activities, such as biking on Burkes Beach, exploring Pinckney Island Wildlife, and golfing on award-winning courses, Hilton Head's many attractions appeal to every type of traveler. Sunsets are truly breathtaking here and an evening sailing trip provides the perfect opportunity to watch the sun dip into the ocean, casting an orange and pink light over the entire island. Local Attractions: - Arthur Hills Golf Course - Robert Trent Jones Golf Course - Hudson's Seafood House On The Docks - Old Oyster Factory Restaurant - A Lowcountry Backyard Restaurant - Alfred's Restaurant - One Hot Mama's American Grill - The Crazy Crab Jarvis Creek - Coligny Beach Park - Islander Beach - Driessen Beach - Folly Fields Beach - Harbour Town - Sea Pines Forest Preserve

Parking information

- Driveway accommodates four cars. - Two-car garage. - No street parking.

We're here to help

Whether you have questions on this home or want us to source other options, we're a message away!

Policies

Check-in: 4:00 PM
Check-out: 10:00 AM
Renter's age: 21+ years old
Quiet Hours: 9:00 PM - 8:00 AM
No smoking allowed
No events allowed
No pets

Cancellation policy

Plans change, we get it.

Enjoy peace of mind when booking with KEY.co.

Partial Refund: Receive a 95% refund when you cancel your reservation at least 60 days before check-in.

Partial Refund: Receive a 45% refund when you cancel your reservation at least 21 days before check-in.

No Refund: Reservations canceled 20 days or less before check-in are not eligible for a refund.

Refunds subject to a 5% processing fee of the total.

Things you need to know

Saturday - Saturday Stay Required during the peak spring and summer months.

The fireplace is also not for guest use.

Pool heating is available for an additional fee of $150 per day and must be requested at least 48 hours in advance. Please note that the maximum pool temperature is 90°F and is dependent on outside weather conditions. Pool heating is available from October 1st through April 1st.

Please note that if the outdoor temperature drops below 50°F, the pool heater may have difficulty maintaining warmer water temperatures.

Wind gusts on Hilton Head Island are strong, unpredictable, and often damage the casement windows. The cost to replace a single window is $5,000. For that reason, guests are not permitted to open the casement windows using handles or other tools. Any attempts to open the casement windows will be considered a violation of house rules and result in a fine. To access fresh air or in case of emergency, please open the sliding glass doors. All bathrooms are equipped with ventilation fans.

The griddle feature of the Wolf range has been deemed a fire hazard and has been intentionally disabled to protect our guests. Any attempt to use this feature will be considered a violation of house rules and result in a $2,000 fine.

Our occupancy includes an additional two beyond the bed count. Trifold floor mattresses and additional linens can be provided upon request.

Each room is outfitted with linens, towels, fluffy pillows, and comforters.

All bookings over 30 days require a security deposit to be charged after booking.

Restrictions

Guests & Occupancy

  • Do not exceed the maximum number of guests listed on the reservation. No overnight visitors beyond registered guests. Unauthorized guests: $500 per person, per day and possible removal without refund.
  • The primary guest is fully responsible for all occupants, their behavior, damages, fines, and compliance with house rules, HOA rules, and local laws.
  • Property may be used only as a personal vacation rental. No subletting, assignment, or unauthorized use. Commercial use is prohibited.

Events & Noise

  • No parties, events, or gatherings exceeding approved occupancy. Any event requires prior written approval and a separate event agreement. Unauthorized events may result in immediate eviction, forfeiture of all payments, and additional event-related fees.
  • Outdoor noise must remain under 60 dBA at all times and is not permitted after 9:00 PM. Noise monitoring devices may be in use (no audio recording).

Prohibited Activities

  • Pets: Pets are not allowed unless explicitly approved in advance. Approved pets are subject to fees and deposits. Unauthorized pets: $100 per day, plus cleaning or damage costs. Service animals permitted as required by law.
  • Smoking/Vaping: No smoking or vaping anywhere on the property. Guests are responsible for all related damage and additional cleaning fees.
  • No illegal drugs, contraband, or unlawful activity of any kind.
  • No firearms, weapons, fireworks, flammable substances, or hazardous materials. Violations may result in $500 fine, immediate eviction, and no refund.
  • No commercial use, professional filming, or photography without prior written approval. Unauthorized use may result in removal and forfeiture of proceeds.
  • Guests may not access neighboring properties or restricted areas. Fines or penalties are the guest’s responsibility.
  • Do not move furniture, install equipment, add locks, or make any physical alterations to the property.

Equipment & Amenities

  • HVAC Settings: Thermostat may not be set below 72°F to prevent system damage.
  • Pools, Hot Tubs & Water Features _(if equipped)_: Use at your own risk. No diving, glass, or intoxicated use. Children must be supervised at all times. Follow posted HOA rules. Damage or misuse fees apply.
  • Bicycles _(if equipped)_: Use at your own risk. Helmets recommended. Guest is responsible for loss, theft, or damage.
  • Parking: Do not exceed the approved number of vehicles. Follow all local and HOA parking rules. Guest is responsible for tickets or towing.
  • Utilities and internet are provided as a convenience. No refunds for service interruptions or malfunctions.
  • Guests must report any malfunction immediately. Damage caused by misuse will be charged to the guest.
  • Locked closets, storage, and owner areas are off-limits.

Checkout & Care

  • Property must be left in reasonable condition. Excessive mess, trash, or stains will result in additional cleaning fees beyond the standard cleaning.
  • All trash must be bagged and placed in bins. Grills must be cleaned after use.
  • Furniture must remain in its original location. Guest is responsible for damages caused by misuse or failure to report issues.
  • All keys and access devices must be returned. Late check-outs without approval will incur a full additional night’s charge.
  • Unauthorized stays beyond checkout are charged at 2x the nightly rate per day, plus damages and associated costs.

Liability & Disclaimers

  • Not responsible for lost, stolen, or damaged personal belongings, including vehicles and packages.
  • Use of pools, hot tubs, docks, bicycles, and similar amenities is at guest’s own risk. No lifeguard on duty.
  • No refunds for weather events, travel disruptions, government actions, or other events outside management control.
  • Property is provided as-is. Photos and descriptions are for marketing purposes and may not reflect minor changes.
  • Exterior cameras and noise monitoring may be in use. Tampering with safety devices is prohibited and may result in removal.