Book Direct. Book Local. Discover professionally managed vacation rentals from trusted local experts.
Find your vacation rental
Search destinations, vacation rentals, or local property managers

Stay at 37 Sailmaster - Gorgeous 2 Bedroom Condo with Amazing Amenities

Condo Rental in Hilton Head Island South Carolina

Discover a dreamy getaway at 37 Sailmaster, a luxurious 2 bedroom condo in Hilton Head Island, SC. With exquisite amenities and numerous nearby activities, this is the ultimate vacation rental for up to 6 guests.

Book Direct
Hilton Head Vacations, Inc.
Connect directly with the local vacation rental manager.
Rates from
$155 / night
Additional fees may apply
Book Direct
Rental overview

Why You'll Love This Rental

37 Sailmaster is a two-story condo in the Shipyard area of Hilton Head Island, South Carolina. With 2 bedrooms and 2 bathrooms, it sleeps up to 6 and is set in a gated community near the beach, with a community pool available on-site. Key features include a private entrance, a balcony/patio space with a grill, and a full kitchen designed for preparing meals during your stay.

Inside, the layout includes a large living and dining area and a galley-style kitchen with granite counters and standard appliances such as a dishwasher, microwave, blender, and coffee maker. Sleeping options include two king beds, a twin bed with trundle, and a queen sleeper sofa in the living room. The condo also provides central heat/AC, internet access, LED TVs, towels/linens, and an in-unit washer/dryer. This is a non-smoking property and pets are not allowed.

Good fit for
Golf trips Tennis trips Honeymoon stays
Sleeps Up to 6 Sleeping includes 2 king beds, a twin with trundle, and a queen sleeper sofa.
Two-Story Layout Two-story condo with the primary bedroom located on the second floor.
Community Pool Access Guests have access to a community pool within the gated community.
Private Grill Patio/balcony space includes a private grill for outdoor cooking.
Washer and Dryer In-unit washer/dryer provided for laundry during your stay.
At a glance

Property Highlights

Waterfront - NearbyLocation Setting
Near a BeachBeach Access
2 BedroomsBedrooms
2 Full BathroomsBathrooms
Sleeps 6Guest Capacity
Pool (Community)Pool
Internet AccessInternet
TelevisionTelevision
YesWasher / Dryer
Location & nearby Explore the Area

This condo is located in the Shipyard area of Hilton Head Island within a gated community and is described as near the beach and waterfront nearby. The Shipyard setting is associated with bike paths, tennis, shopping, restaurants, and golf, and the listing notes free beach parking in Shipyard. The broader Hilton Head Island area is described as offering extensive bike paths, golf, tennis/pickleball, shopping, dining, and beach access.

Plan your stay

Rates & Availability (USD)

Rates from
$155 per night
4-day minimum stay
Check current rates & availability

Live booking details are maintained by Hilton Head Vacations, Inc..

Check Availability

Availability Calendar

Use the calendar as a guide, then confirm current availability directly with the manager.

Available Booked
About this rental

About This Rental

37 Sailmaster is a two-story condo in the Shipyard area of Hilton Head Island. The home is located in a gated community and is listed as near the beach, with access to a community pool. A private entrance leads into a spacious main living level that combines the living room and dining area, creating a practical setup for shared time indoors.

The kitchen is a galley style layout with granite counters and a full set of core appliances and tools for meal prep, including a dishwasher, microwave, blender, and coffee maker. The living room includes a smart/LED TV for streaming, and the condo offers internet access. For outdoor cooking, the patio/balcony area includes a private grill.

Sleeping is arranged across two private bedrooms plus a sleeper sofa in the living room. The primary bedroom is upstairs and includes a king bed and an en suite bathroom. The guest bedroom includes a second king bed along with a twin bed and trundle, and the living room provides a queen sleeper sofa, bringing total occupancy to 6.

Additional conveniences include central heat/AC, ceiling fans, towels and linens, and an in-unit washer/dryer with basic soaps and laundry soap noted. The property is non-smoking and does not allow pets. Activities mentioned in the area include beach time, boating, fishing, kayaking, surfing, scuba diving, and golfing.

Wonderful luxury vacation condo at 37 Sailmaster in Shipyard Resort with great beach access. Two bedroom two and a half bath townhome in Shipyard with community pool and free beach parking. Very large living room and dining room with a large galley style kitchen. The kitchen is fully stocked with pots and pans to prepare the family meals. Living room has a large flat screen smart TV to stream all the favorite shows. Nice size patio has a private barbeque grill to cook steaks and chicken. Master bedroom is on the second floor with a king size bed and en suite master bath. Guest room has another king size bed with twin and trundle underneath. Living room has a sleeper sofa so the condo can sleep six people comfortably. Your vacation rental includes bike rentals and beach gear with your stay. 37 Sailmaster in Shipyard is professionally managed and operated by Hilton Head Vacations, Inc, a locally owned company. STR Permit is 026169

Shipyard has plenty of free beach parking right beside the Sonesta Hotel. You can also ride your bike to the beach in Shipyard or go to Coligny shops and restaurants too. Shipyard has miles of shaded bike paths to excersize on. Van Der Meer Tennis has world class tennis and pickle ball facilities lighted and covered located right in Shipyard. Shipyard offers 27 holes of golf for you to practice your game, bring a few extra balls, there are some good size lagoons too. Sonesta Hotel has several restaurants and bars on Shipyard along with the pub at the Shipyard pro shop.

Forest Beach is just around the corner with the Celebration town of Hilton Head park with a giant Pirate Ship playground. Coligny has over 60 shops and restaurants, just minutes away. You can enjoy the oceanfront Tiki Hut, Frosty Frog cafe or fine dining at the Sage Room and the best breakfast in town is at the Plantation Deli, all just around the corner from Shipyard.

Hilton Head Island offers over 30 golf courses, 400 tennis and pickle ball courts, 117 miles of bike paths, 250 shops, over 200 restaurants and 17 miles of beautiful white sandy beaches. During your vacation, you have options, go play golf, tennis, go swimming in the ocean, sunbathe, fishing, para sailing, deep sea fishing, kayaking, jet skiing or just relax by the pool. You can sleep all day or be as active as you like while enjoying great accommodations at 37 Sailmaster in Shipyard.

Please book online and we will send you a secure reservation with all the check in instructions. Your family will have a great time. We look forward to having you stay with us. Thank you, Hilton Head Vacations, Inc.

Your Hilton Head Island vacation just got even better with our brand-new VayKLife Bike Rentals and Beach Gear Included program! For all new bookings made on or after 4/15/25 of 3–21 nights, you’ll receive complimentary bike rentals and beach gear credit, ensuring your coastal getaway is as effortless as it is unforgettable. With your VayKLife credit, you can select from a premium collection of beach essentials, all delivered straight to your door—no hassle, just fun. Keep an eye out for an email from VayKLife to customize your gear selection and get ready to experience Hilton Head like never before!
Things to enjoy

Activities and Special Interests

This property provides access to the following activities and special interests:

Golfing
Honeymoon
Boating
Canoeing
Fishing
Fly Fishing
Kayaking
Beach
Deep Sea Fishing
Ocean
Surfing
Scuba Diving
Wind Surfing
What's included

Property Amenities

Featured Amenities

Television
Washer/Dryer
Dishwasher
Pool (Community)
Grill
Internet Access

Property Features

Towels/Linens
Ceiling Fan(s)
Balcony
Microwave
Full Kitchen
Coffee Maker
Blender
Gated Community

Suitability

Children Welcome

Other Property Amenities

Private Entrance
Location: Shipyard
Property Type: Condo/Villa
Two Story
Queen Sleeper Sofa
Living Room
Sofa Bed/Foldout Couch
Central Heat/AC
Carpet Floors
Soaps Basic
Laundry Soap
Iron w Ironing Board
Granite Counters in Kitchen
Guest Room 1
Master Bedroom
Twin Bed 1
King Bed 2
King Bed
Private Bedrooms
Trundle Bed
Tennis
Shopping
Bike Paths
Restaurants
Massage Nearby
Dining Area
Half Bath 1
Guest Bath 1
Master Bath
Family Oriented Accommodations
NON Smoking
Quality Accommodations
Winter Monthly Rentals
Hardwood Floors
LED TVs
Accepts Credit Cards
Smoke alarm
Fire Extinguisher
Pets Not Allowed
Helpful details

Frequently Asked Questions

37 Sailmaster 2 BR 2.5 BA Shipyard is located in Hilton Head Island, South Carolina.

37 Sailmaster 2 BR 2.5 BA Shipyard accommodates up to 6 guests.

2 Bedrooms and 2 Full Bathrooms.

The listed beach access for 37 Sailmaster 2 BR 2.5 BA Shipyard is Near a Beach.

Yes. The property lists Pool (Community).

The property lists a 4-night minimum stay.
Local management

Professionally Managed By

Hilton Head Vacations, Inc.
In business since 2000
View Manager Profile

Questions about this rental?

Connect directly with Hilton Head Vacations, Inc. for current rates, availability, and local assistance.

Contact Hilton Head Vacations Reservations and Guest Services
Daytime Phone Evening Phone
Property reference
#166001 · 37 Sailmaster 2 BR 2.5 BA Shipyard
Keep exploring

Similar Rentals from Hilton Head Vacations

More rentals from the same manager, prioritized by location, property type, size, and setting.