29 Sailmaster: Stunning Open Floorplan, Free Pool and Bikes. Sleeps 4

Hilton Head Island, South Carolina
$311 avg/night Minimum Stay 3 Nights
Bed 2

Bed

Bath 2

Bath

Home Villa

Property Type

Sleep 4

Max Sleeps

Night 3 nights

Min Stay

Proudly hosted by Island Rentals of Hilton Head, this beautifully updated villa at 29 Sailmaster Common is a modern coastal retreat located within the gated Shipyard Resort. Thoughtfully designed with upscale finishes and designer touches throughout, this villa offers relaxed luxury in one of Hilton Head Island’s most sought-after resort communities—close to the beach, golf, bike paths, and all the island has to offer.

The welcoming entryway features a custom bench and coatrack and opens into a spacious open-concept living area that spans the entire first floor. The updated kitchen is both stylish and functional, featuring modern cabinetry, updated countertops, and appliances, fully equipped for preparing meals for the whole family. The kitchen flows seamlessly into the dining area, highlighted by a rustic dining table and statement chandelier, before opening into the inviting living room with a large sectional sofa and flat-screen TV—perfect for gathering after a day of island adventures.

Outdoor living is a highlight of this home, with a private cement patio offering both a comfortable lounge area and an outdoor dining table. Whether you’re enjoying morning coffee, grilling dinner, or unwinding in the evening, this space provides a peaceful setting surrounded by the natural beauty of Shipyard Resort.

Upstairs, the villa features two well-appointed bedrooms, each with access to a full bathroom. The primary bedroom offers a King bed, flat-screen TV, and an en suite bathroom, creating a relaxing private retreat. The guest bedroom includes a Queen bed with a full bathroom located just steps away in the hallway. Two twin inflatable mattresses are also available, making this villa a great option for families traveling with children.

Guests will enjoy thoughtful amenities including four complimentary adult bicycles, four backpack beach chairs, secure WiFi, a gas grill, and access to the community pool (open April through October). One car pass is included with your stay, with the option to purchase an additional pass. Come experience the perfect balance of comfort, style, and location at Sailmaster Common in Shipyard Resort.

• 2 Bedrooms , 2.5 Baths (King, Queen)
• Gas Grill
• Outdoor Dining Area
• Free Secure Wifi
• 4 Adult Bicycles
• 4 Backpack Beach Chairs
• Community Pool (Open April through October)
• 1 Car pass is included with your stay, 1 additional pass may be purchased.

* All Reservations made for a duration of 1 month (28 Days) or longer are non refundable. Travel Insurance is highly recommended.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Kitchen Island Microwave Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • INTERNET

    Free WiFi, With Speed Of 250+ Mbps (good For 3–5 People Or Up To 10 Devices)
  • OUTDOORS

    Gas Grill Patio
  • POOL/SPA

    Shared/communal Pool
  • BATHROOMS

    2.5 Bathrooms Bathtub Or Shower Towels Provided
  • LANGS SPOKEN

    English Spanish
  • THINGS TO DO

    Bicycle On Site
  • ENTERTAINMENT

    Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 4

Map Map

School District Rates & Availability

Review Review

  • Becky

    Submitted Aug 21, 2023

    Stayed Aug 16, 2023

    The property was beautiful and peaceful, we truly enjoyed our stay at the condo. The beds were extremely firm, the HVAC unit provided perfect temperatures on the main floor but much harder to maintain cooler temperatures upstairs. I hope to book this condo again for my September trip to HH.

  • Mary S.

    Submitted Oct 26, 2025

    Stayed Oct 4, 2025

    A sewer smell in service area and kitchen which spread through unit which began on and off throughout our stay especially getting worse at night. After the smell got unbearable we decided to pack up and leave notifying management of the issue. They met us at the unit however there was little to no smell upon arrival. I am not a plumber so cannot say why the smell would come and go except for possibly it being over 12 hours since any of bathroom facilities had been used. I asked to be moved to another unit or issue a refund for the last week. Never heard back from anyone with the rental company. There would have been no reason for us to leave if there had not been a smell and lose 1,000.00 in rental cost. I feel they should have offered to move us to another location. Overall the management company could have handled the situation with moving us to another location.

  • Jake S.

    Submitted Mar 1, 2025

    Stayed Dec 31, 2024

    Excellent property and primo location

  • Joe S.

    Submitted Dec 27, 2024

    Stayed Dec 22, 2024

    Great would do again

  • Brian H.

    Submitted Oct 5, 2024

    Stayed Sep 28, 2024

    Great location. Close to beach. Much louder than we are accustomed to when we go to Hilton head. Place could use a thorough cleaning (lots of hair on the bathroom floors and a couple bottles under the couch), but otherwise very nice

  • Diane J.

    Submitted Aug 12, 2024

    Stayed Jul 20, 2024

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The house is beautiful and it had everything we could’ve ever thought to need. So well decorated and absolutely perfect!

  • Wendy F.

    Submitted Jul 2, 2024

    Stayed Jun 15, 2024

    Wonderful place to stay ! So relaxing! Close to everything and very convenient!

  • Gordon M.

    Submitted Jun 12, 2024

    Stayed May 24, 2024

    Clean, well maintained. Great location I have stayed here before and would stay there again

  • Sonya W.

    Submitted Jun 8, 2024

    Stayed Jun 2, 2024

    The condo was very clean and beautiful. It is a little hike to the pool and to get the parking pass was off site. Beautiful foliage and wild life. I felt communication with property manager could improve. I didn’t receive a welcoming message once booked. I just noticed money taken out of my account when booked. I had to reach out the week of our trip making sure everything was set up and a go. That made me a little nervous as all the other Vrbos I’ve booked has had communication of some sort. All in all, the trip was good and we were happy.

  • Melissa M.

    Submitted Apr 8, 2024

    Stayed Mar 30, 2024

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The rental was as described! Updated, clean and perfect for our family of 4! Close to all that HHI has to offer. The beach access had parking for bikes and cars. We had a fantastic time and would happily come back!

  • Mary Pat Pat M.

    Submitted Mar 25, 2024

    Stayed Feb 10, 2024

    Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: 5 Stars....We had a Wonderful stay in this absolutely beautiful unit. Recently refurbished and redecorated, it was lovely and very well equipped. The patio, as mentioned, was a little bit of paradise. Everything was as pictured. You can’t beat the location in Shipyard, walking, biking, golfing; we love Hilton Head and all that it has to offer. Island Rentals communicated really well, and was very quick to respond to two minor issues. Very helpful, so much, that we chose to rent (another property) with them next year. Very reliable.

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Total

Includes taxes and fees
$311+
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