House in Hilton Head Island, SC
10 guests · 5 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
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About this house rental
Gloucester 36
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
Gloucester 36 offers everything you would want for your Hilton Head vacation: a great location, incredible amenities, superb decoration, and plenty of space and privacy, perfect for a family getaway. This ground floor retreat has everything you and your guests could need on the main and only level of the house. Upon entering, you'll notice high-end furniture and finishes and plenty of light. To your right, you'll find a bedroom/studio equipped with a twin daybed with a trundle, a well-equipped desk, and a small flatscreen TV on a stand. Right off the studio is the laundry room with a private washer/dryer, a sink, cleaning supplies, and an Avalon water dispenser. Then, you'll come across the fully-equipped kitchen–a cook's paradise. It's spacious enough to move around freely while cooking and comes equipped with plenty of counter space, modern appliances that include a double-door, full-size fridge, stove, dishwasher, coffee maker, blender, toaster, double oven, electric oven, mixer, utensil, wine fridge, mini-fridge, and even a small flatscreen TV on the counter! The kitchen island seats three and the dining table right off the kitchen has space for up to six people.
As you leave the kitchen, your jaw will drop at the sight of the spacious living room area, which is actually separated into two smaller areas. The media area is made up of a large, wall-mounted flatscreen TV surrounded by four recliners (one is a double), a desk, a DVD player, a gaming console with games included, a record player, and a ceiling fan. The other part of the living area is the perfect place to unwind–here you'll find plenty of seating such as two chairs and a high table, a chaise lounge, a sofa with a footstool, two armchairs, and a two-person sofa. There are plenty of magazines throughout the home, so don't hesitate to grab one of them, snuggle up on the couch, and get lost in them. A quaint see-through room divider will take you to the main dining room featuring high-end touches, a large dining table with space for up to eight dinner guests, a convenient wine cooler, and a wine rack.
The screened porch is a great place to relax if you're looking for some seclusion from the group–wall-to-wall windows allow views of the marvelous backyard, giant trees, deck, and pool area. The inviting sectional sofa and wall-mounted flatscreen TV create the perfect spot for a relaxing afternoon. Air conditioning and one ceiling fan in each room will be ideal for warm days and to stay away from the heat. This dog-friendly retreat offers five bedrooms and three full bathrooms. The main bedroom has a king bed, ceiling fan, a wall-mounted flatscreen TV, drawers, a large closet, and a chaise lounge. Off the main bedroom is an ensuite bathroom with exquisite decor, a two-person vanity, a walk-in tiled shower, a makeup vanity, a towel heater, and yes, a wall-mounted flatscreen TV. Bedroom number two has a queen bed, a closet, a ceiling fan, and a flatscreen TV on top of a drawer. Bedroom number three has a queen bed as well, a large wall-mounted TV and mirror, a closet, a ceiling fan, and a folding ottoman. And last, but not least, bedroom number four has a queen bed, a ceiling fan, a small sofa at the foot of a bed, and a flatscreen on top of a drawer. One full bathroom features a double vanity and a walk-in shower, while the other has a one-person vanity and a walk-in shower.
Outside is all about entertaining with a partially covered patio with two ceiling fans and a seating area with a two-person sofa and four outdoor chairs, a private outdoor pool with pool toys for the children and kids at heart, a pool area with a poolside bar with a flatscreen TV and four stools, six lounge chairs, one seating area near the bar with a sofa and two cushioned lounge chairs, a private gas grill, a deck with an outdoor dining area for six people, and another seating area near the pool with three chairs, a table, and a lounge chair. The front porch offers another great relaxation spot with a ceiling fan, a swing, and a convenient basketball hoop.
What’s nearby:
Shipyard Plantation is an elite resort community with a charming coastal atmosphere on the south end of Hilton Head Island. The 803-acre gated plantation boasts a 27 hole championship golf course at Shipyard Golf Club, and Van Der Meer Shipyard Racquet Club, one of the top 50 tennis resorts in the country. Relaxing comes naturally on the beach at Shipyard Beach Club and if you’re feeling adventurous, take a scenic stroll or bike ride down the winding trails. You’ll also find yourself within walking distance to the heart of Hilton Head, Coligny Plaza.
Things to Know
Free high-speed WiFi
Please note that the private pool is not heated.
One parking pass for the Shipyard Beach Club Parking.
Please note E-bikes are not allowed.
This property is managed by Vacasa South Carolina LLC.
If you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.
Parking notes: There is parking available for a fee and charges will apply for 5 vehicles.
This rental is located on floor 1.
Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.
Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'
Gloucester 36 offers everything you would want for your Hilton Head vacation: a great location, incredible amenities, superb decoration, and plenty of space and privacy, perfect for a family getaway. This ground floor retreat has everything you and your guests could need on the main and only level of the house. Upon entering, you'll notice high-end furniture and finishes and plenty of light. To your right, you'll find a bedroom/studio equipped with a twin daybed with a trundle, a well-equipped desk, and a small flatscreen TV on a stand. Right off the studio is the laundry room with a private washer/dryer, a sink, cleaning supplies, and an Avalon water dispenser. Then, you'll come across the fully-equipped kitchen–a cook's paradise. It's spacious enough to move around freely while cooking and comes equipped with plenty of counter space, modern appliances that include a double-door, full-size fridge, stove, dishwasher, coffee maker, blender, toaster, double oven, electric oven, mixer, utensil, wine fridge, mini-fridge, and even a small flatscreen TV on the counter! The kitchen island seats three and the dining table right off the kitchen has space for up to six people.
As you leave the kitchen, your jaw will drop at the sight of the spacious living room area, which is actually separated into two smaller areas. The media area is made up of a large, wall-mounted flatscreen TV surrounded by four recliners (one is a double), a desk, a DVD player, a gaming console with games included, a record player, and a ceiling fan. The other part of the living area is the perfect place to unwind–here you'll find plenty of seating such as two chairs and a high table, a chaise lounge, a sofa with a footstool, two armchairs, and a two-person sofa. There are plenty of magazines throughout the home, so don't hesitate to grab one of them, snuggle up on the couch, and get lost in them. A quaint see-through room divider will take you to the main dining room featuring high-end touches, a large dining table with space for up to eight dinner guests, a convenient wine cooler, and a wine rack.
The screened porch is a great place to relax if you're looking for some seclusion from the group–wall-to-wall windows allow views of the marvelous backyard, giant trees, deck, and pool area. The inviting sectional sofa and wall-mounted flatscreen TV create the perfect spot for a relaxing afternoon. Air conditioning and one ceiling fan in each room will be ideal for warm days and to stay away from the heat. This dog-friendly retreat offers five bedrooms and three full bathrooms. The main bedroom has a king bed, ceiling fan, a wall-mounted flatscreen TV, drawers, a large closet, and a chaise lounge. Off the main bedroom is an ensuite bathroom with exquisite decor, a two-person vanity, a walk-in tiled shower, a makeup vanity, a towel heater, and yes, a wall-mounted flatscreen TV. Bedroom number two has a queen bed, a closet, a ceiling fan, and a flatscreen TV on top of a drawer. Bedroom number three has a queen bed as well, a large wall-mounted TV and mirror, a closet, a ceiling fan, and a folding ottoman. And last, but not least, bedroom number four has a queen bed, a ceiling fan, a small sofa at the foot of a bed, and a flatscreen on top of a drawer. One full bathroom features a double vanity and a walk-in shower, while the other has a one-person vanity and a walk-in shower.
Outside is all about entertaining with a partially covered patio with two ceiling fans and a seating area with a two-person sofa and four outdoor chairs, a private outdoor pool with pool toys for the children and kids at heart, a pool area with a poolside bar with a flatscreen TV and four stools, six lounge chairs, one seating area near the bar with a sofa and two cushioned lounge chairs, a private gas grill, a deck with an outdoor dining area for six people, and another seating area near the pool with three chairs, a table, and a lounge chair. The front porch offers another great relaxation spot with a ceiling fan, a swing, and a convenient basketball hoop.
What’s nearby:
Shipyard Plantation is an elite resort community with a charming coastal atmosphere on the south end of Hilton Head Island. The 803-acre gated plantation boasts a 27 hole championship golf course at Shipyard Golf Club, and Van Der Meer Shipyard Racquet Club, one of the top 50 tennis resorts in the country. Relaxing comes naturally on the beach at Shipyard Beach Club and if you’re feeling adventurous, take a scenic stroll or bike ride down the winding trails. You’ll also find yourself within walking distance to the heart of Hilton Head, Coligny Plaza.
Things to Know
Free high-speed WiFi
Please note that the private pool is not heated.
One parking pass for the Shipyard Beach Club Parking.
Please note E-bikes are not allowed.
This property is managed by Vacasa South Carolina LLC.
If you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.
Parking notes: There is parking available for a fee and charges will apply for 5 vehicles.
This rental is located on floor 1.
Damage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.
More information can be downloaded from the "Rental Agreement" on the checkout page.
Due to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
Map of Hilton Head Island, SC
Ratings and reviews
10 / 10Outstanding·Aug 2025
Our vacation home fit our needs with having ages 7 to 77! The pool was a big hit as well as being able to cook outdoors. I would probably update the office/trundle bed into a bedroom for our granddaughters, but they adapted easily! Will try to come back in 2026!
10 / 10Outstanding·Jun 2025
The pool with the tiki bar and TV were amazing. I loved the spacious layout. I would totally book this property again.
10 / 10Outstanding·May 2025
This house was in the perfect location. Typically I rent houses in Sea Pines but this is the first time I rented in Shipyard. The house is so perfectly centralized it was so easy getting places. I’ve rented numerous places on Island and this was one of the best.
6 / 10Average·May 2024
Not much seeing we couldn't accomplish much in the house besides sleep on concrete beds.
$$$$
Top rated by guests
9.1Outstanding
(71 Ratings)
"Our vacation home fit our needs with having ages 7 to 77! The pool was a big hit as well as being able to cook outdoors. I would probably update the office/trundle bed into a bedroom for our granddaug..."
Regina H.Don't miss out! Price and availability may change
