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

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Nestled in the Shipyard Resort, Sailmaster Common offers modern luxury and attention to detail. Unwind in the spacious living room with a large flat screen television or cook meals for your family in the beautifully updated kitchen. The villa features an outdoor cement patio perfect for lounging or dining al fresco, as well as access to a community pool and secure WiFi.

Reviews

9.4 out of 10
Exceptional

Entire home

2 bedrooms3 bathroomsSleeps 4

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

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About this property

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

  • 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.

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

Property amenities

Pool/Spa

  • Communal pool

Internet

  • Available in the villa: Free WiFi

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub or shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Gas grill
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the sea

Things to do

  • Bicycles

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with EU regulations about consumer rights, property booking services are not subject to the right of withdrawal.

About the area

Located by the sea, this villa is in South End, a neighbourhood in Hilton Head Island. Shelter Cove Harbour and Palmetto Dunes Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Sea Pines Forest Preserve and Coligny Beach. The Sandbox and Pirate's Island Adventure Golf are also worth visiting. Visit our Hilton Head Island travel guide
View more Villas in Hilton Head Island
Map
Hilton Head Island, SC

What's nearby

  • HiltonHeadIsland_TheVillageatWexford_0006
    The Village at Wexford
    18 min walk - 1.6 km
  • HiltonHeadIsland_ColignyPlaza_6134196_0004
    Coligny Plaza
    3 min drive - 1.7 km
  • Coligny Beach
    Coligny Beach
    3 min drive - 2.7 km
  • Shipyard Golf Course
    5 min walk - 0.4 km
  • The Sandbox
    3 min drive - 2.0 km

Getting around

  • Hilton Head Island, SC (HHH)
    22 min drive

Restaurants

  • Fish Seafood & Raw Bar
    4 min drive
  • Java Burrito
    18 min walk
  • Frosty Frog Cafe
    4 min drive
  • Circle K
    3 min drive
  • The Bank
    18 min walk

Frequently asked questions

Is 29 Sailmaster: Stunning Open Floorplan, Free Pool and Bikes. Sleeps 4 pet-friendly?

No, pets are not allowed at this property.

What time is check-in at 29 Sailmaster: Stunning Open Floorplan, Free Pool and Bikes. Sleeps 4?

Check-in begins at 4:00 PM.

What time is check-out at 29 Sailmaster: Stunning Open Floorplan, Free Pool and Bikes. Sleeps 4?

Checkout is at 10:00 AM.

Where is 29 Sailmaster: Stunning Open Floorplan, Free Pool and Bikes. Sleeps 4 located?

Located in South End, this villa is 0.8 mi (1.3 km) from The Village at Wexford and 1.4 mi (2.3 km) from Coligny Beach. Shipyard Golf Course and Lowcountry Celebration Park are also within 1 mile (2 km).

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

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 21 out of 29 reviews
Rating 8 - Good. 6 out of 29 reviews
Rating 6 - Okay. 1 out of 29 reviews
Rating 4 - Poor. 1 out of 29 reviews
Rating 2 - Terrible. 0 out of 29 reviews

9.2

Cleanliness

9.8

Location

10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Wendy F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved our stay!

Wonderful place to stay ! So relaxing! Close to everything and very convenient!
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Beata K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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
Stayed 5 nights in Aug 2023
Verified

8/10 Good

Jake S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Jake

Excellent property and primo location
Stayed 59 nights in Dec 2024
Verified

10/10 Excellent

Gordon M.

Liked: Cleanliness, communication, location, listing accuracy

Nice

Clean, well maintained. Great location I have stayed here before and would stay there again
Stayed 8 nights in May 2024
Verified

10/10 Excellent

Brian H.

Liked: Check-in, communication, location, listing accuracy

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
Stayed 7 nights in Sep 2024
Verified

10/10 Excellent

Stacy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 7 nights in Sep 2023
Verified

10/10 Excellent

Michael M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tennis

Great location for tennis at Van de Meer. Wonderful property with great amenities and location to fabulous restaurants.
Stayed 3 nights in Sep 2023
From a partner site

10/10 Excellent

Diane J.

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!
Stayed 7 nights in Jul 2024
Verified

10/10 Excellent

Mary S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 4 nights in Oct 2023
Verified

8/10 Good

Sonya W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice and clean condo

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.
Stayed 6 nights in Jun 2024
From a partner site

10/10 Excellent

Melissa M.

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!
Stayed 7 nights in Mar 2024
From a partner site

10/10 Excellent

Mary Pat Pat M.

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.
Stayed 42 nights in Feb 2024
From a partner site

10/10 Excellent

Sharon S.

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.
Stayed 7 nights in Sep 2023
Verified

8/10 Good

Diane P.

Liked: Cleanliness, communication, location, listing accuracy

Beautiful Accommodations

Villa was fully equipped and was very clean. Loved our stay!
Stayed 4 nights in May 2023
Verified

10/10 Excellent

Joe S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Christmas get away

Great would do again
Stayed 5 nights in Dec 2024
Verified

10/10 Excellent

Kendall F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 5 nights in Apr 2023
Verified

10/10 Excellent

Becky

Liked: Cleanliness, amenities, property conditions & facilities, communication
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.
Stayed 3 nights in Aug 2023
Verified

10/10 Excellent

Gordon M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect

Recently renovated with GREAT taste! Had everything there for us! GREAT location. Is much better than the description. It was a TEN!!!
Stayed 5 nights in May 2023
Verified

8/10 Good

Brian K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Patio

The patio area was amazing. It felts very secluded and had multiple seating locations depending on your reasons to be there. Two seats were in the shade , two in the sun and four at the dining table. The interior was beautifully decorated. The only downfall was the beds. The master was extremely firm and the 2nd was only moderately better.
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

Joyce J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 7 nights in Jul 2023
Verified

8/10 Good

Jes R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Terrific location

We were a large party and needed some extra space. This accommodation was terrific for us. The space is very clean and comfortable. The toilet seat was cracked in the downstairs bathroom, but I alerted the manager and we did not use that bathroom. The fan in the master bathroom makes a loud cranking noise when at “high” but it I wasn’t too bad. Overall it’s was a great space.
Stayed 7 nights in Jul 2023
Verified

4/10 Poor

Mary S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 21 nights in Oct 2025
Verified

10/10 Excellent

Janet C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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.
Stayed 8 nights in May 2023
From a partner site

10/10 Excellent

Rebecca S.

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.
Stayed 7 nights in Jul 2023
From a partner site

10/10 Excellent

Debra B.

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!
Stayed 5 nights in Apr 2023