Villa - Rating 5 (25)

29 Sailmaster Common

$560.00 - $1,820.00 / week + taxes & fees
Bedroom 2 bedrooms
Bathroom 2 baths
Half-Bathroom 1 half-baths
Guests 4 guests
Pets Not Allowed Pets Not Allowed
  • Address: 29 Sailmaster Common
  • Location: Shipyard
  • Type: Villa
  • View: Wooded View
Location Location
Description Description
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 coat rack 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.

Availability Calendar Availability Calendar
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February 2026
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Swipe Swipe for Availability
Amenities 32 Amenities
  • Bicycles
  • Blender
  • Cable TV
  • Ceiling Fans
  • Central Air
  • Coffee Maker
  • Community Pool
  • Cookware
  • Deck / Patio
  • Dining Area
  • Dishes & Utensils
  • Dishwasher
  • Free Wifi
  • Gas Grill
  • High Speed Internet
  • Ice Maker
  • Ironing Board
  • Keurig
  • Linens
  • Living Room
  • Microwave
  • Near The Ocean
  • Patio
  • Refrigerator
  • Stove
  • Toaster
  • Towels
  • Washer & Dryer
  • Air Conditioning
  • Digital Deadbolt
  • Non Smoking Only
  • Wheelchair inaccessible
Reviews Rating 5 (25) Reviews
Rating 5
Everything was perfect
Anonymous - Posted: 8/13/2025
Thanks for your review, Anna! We're glad everything was perfect during your stay. We look forward to hosting you again!
Island Rentals of Hilton Head staff
Rating 5
Beautiful Airbnb with a convenient private beach access! Loved staying here!
Anonymous - Posted: 7/7/2025
Thanks for your review, Peyton! Glad you enjoyed the private beach access. We hope to welcome you back soon!
Island Rentals of Hilton Head staff
Rating 5
Amazing!!!
What a beautiful condo! It has everything we needed to feel at home. The decor is perfect and the management company was helpful with any questions! The bikes were an added bonus- we went everywhere with them on the island and had the best time! Highly recommend!
Anonymous from Secaucus - Posted: 6/30/2025
Rating 5
Christmas get away
Great would do again
Anonymous - Posted: 12/27/2024
Thank you for your review, Joe! So glad you enjoyed your holiday here on the island. We hope you come back and rent with us again!
Island Rentals of Hilton Head staff
Rating 5
Great location
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
Anonymous - Posted: 10/5/2024
Thanks for your review, Brian! We hope you enjoyed your trip and that you'll come rent with us again!
Island Rentals of Hilton Head staff
Rating 5
It was WONDERFUL!! We will be coming back !
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!
Anonymous - Posted: 8/12/2024
Thank you for your review! We hope you'll come back and rent with us, again!
Island Rentals of Hilton Head staff
Rating 5
Beautiful home! Aside from a HOA board member reporting us for where a bike was dropped off we had a great experience here! Felt like home away from home.
Anonymous - Posted: 8/3/2024
Glad you enjoyed your home! Sorry about the board member. If Airbnb had the ability to add emojis, I would add the hand covering my face one here. I'm glad that didn't take away from your trip. We hope you'll return and rent through us again!
Island Rentals of Hilton Head staff
Rating 5
Loved our stay!
Wonderful place to stay ! So relaxing! Close to everything and very convenient!
Anonymous - Posted: 7/2/2024
Rating 5
We had a really nice stay at this property. Everything was as advertised and was an excellent value. It was a great space for two couples with two large beds and two separate en suites. The beds were firm but comfortable. We appreciated the quiet atmosphere and liked the Shipyard area overall. The kitchen was well stocked with essential cookware and dishes and having a gas grill was a big plus. The bikes and beach chairs were also helpful. We used the pool almost daily and it was never crowded. The beach access is also convenient. We had one very minor maintenance issue which was resolved within 45 minutes so communication was good. My only minor points of improvement would be that the pillows could use an upgrade (plus not enough pillow cases for the extra pillows) and having some more essentials in the kitchen (e.g., more trash bags, spray to clean the counter, etc.) - it's tough to buy all the basics for a short stay. But, would definitely recommend and would stay again.
Anonymous - Posted: 6/15/2024
Rating 5
Nice
Clean, well maintained. Great location I have stayed here before and would stay there again
Anonymous - Posted: 6/12/2024
Rating 5
Fantastic Week!
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!
Anonymous - Posted: 4/8/2024
Rating 5
Five Stars
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.
Anonymous - Posted: 3/25/2024
Rating 5
Hilton Head Gathering
The property was excellent for the four of us. Very clean and equipped with everything you will need. Complete privacy in the two bedrooms. It is exactly as it is described. The pool is in short walking distance from the unit. We will differently rent the unit again as it is perfect!!! Thank you to the owners for the very nice furnishings.
Anonymous - Posted: 10/27/2023
Rating 5
HHI Golf trip
The property is in a great location. The amenities are plentiful. The outdoor space of this house is amazing. Spent most our time enjoying the patio!
Anonymous - Posted: 10/7/2023
Rating 5
Sailmaster
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: This property was great. Quiet location, pool was wonderful and bikes were a excellent addition. We had to wait for the cleaning company to finish cleaning when we checked in at 4:00. The front courtyard needs some weeding, but overall a wonderful place to stay. Will stay again when in HHI.
Anonymous - Posted: 10/2/2023
Rating 5
Tennis
Great location for tennis at Van de Meer. Wonderful property with great amenities and location to fabulous restaurants.
Anonymous - Posted: 9/22/2023
Rating 5
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.
Anonymous - Posted: 8/21/2023
Rating 5
Great stay!
We had a wonderful stay and thoroughly enjoyed this beautifully updated home. The patio was a huge plus. It was private, close to the beach and pool. The bikes and beach chairs were a plus. Highly recommend and we will definitely plan on staying here again
Anonymous - Posted: 8/7/2023
Rating 5
Grands Getaway
Rating Details: The property manager was very helpful. The vacation rental was very clean. 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: We chose this condo as we were familiar with the area from previous stays on HHI. Our two youngest grandsons asked to go to the beach before the new school year. They love the beach! We have friends on Daufuskie. We split our time and enjoyed both!No contact with the mgmt co. Picked up the envelope, never a problem.
Anonymous - Posted: 7/25/2023
Rating 5
Very nice
Very nice condo. The place was decorated very beach like. The master bedroom bed too firm. Drive to the beach 3 minutes away. There were no kitchen amenities like sandwiches baggies, foil, plastic wrap. Would absolutely stay there again.
Anonymous - Posted: 7/18/2023
Rating 5
Perfection
Loved our recent stay at 29 Sailmaster. The villa had everything we needed. Very clean and I am very picky! All the furniture and beds were very up to date and comfortable. The unit is decorated very tastefully and the kitchen had everything you could possibly need. The walk to the beach is a little over a mile which can be a challenge if you are lugging a lot of stuff, but this trip was just my husband and I so it was a non issue. We did park a couple of times by the beach or he dropped me off with all our stuff and then rode the bike back. The bikes and beach chairs provided by the rental were a nice added bonus. Just make sure your parking pass has the green stamp on it that allows parking in the beach lot. Ours did not and we got a warning ticket our last day here. I let Island Rentals know so that other renters in Shipyard don’t run into the same problem. Overall, I would rent this place again in a heartbeat.
Anonymous - Posted: 6/17/2023
Rating 5
Perfect
Recently renovated with GREAT taste! Had everything there for us! GREAT location. Is much better than the description. It was a TEN!!!
Anonymous - Posted: 5/30/2023
Rating 5
Watching and Playing Golf Hilton Head
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: Fantastic stay at 29 Sailmaster Common in Shipyard on Hilton Head Island. Great location, well appointed condo for husband and myself to attend the Heritage Tournament and play golf around the island. Enjoyed the layout of the condo; very clean, ready on time, bikes to ride and lovely patio area. This is from a picky person but I would definitely want to stay here again!
Anonymous - Posted: 4/22/2023
Rating 5
Great Location
This property made for a great Hilton head stay. Bikes being available made our way around the island super easy. Short bike ride to coligny plaza or 10 min to the beach access. It had everything we needed and we would stay here again!
Anonymous - Posted: 4/15/2023
Rating 5
Great spot
Rating Details: The property manager was more than helpful. The vacation rental was very clean. 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: Spent 4 nights in this unit. Absolutely awesome unit and location. Seconds from Shipyard golf course and 5 minute bike ride from restaurants and bars. Only complaint was backyard patio could be cleaned up a bit but very minor issue.
Anonymous - Posted: 4/11/2023
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