No. 01
43 South Beach Lagoon
Vacation Home
8 bedroom
sleeps 24
Beachfront
private pool
Beachfront property with sea view and outdoor swimming pool.
Hilton Head's foot-shaped barrier island sits just across the Georgia line. Gated plantation communities (Sea Pines, Palmetto Dunes, Shipyard) house most luxury rentals. Golf is everywhere, the beach is firm enough to bike, and October is the sweet spot for weather plus price.
StateSC
Peak seasonJune to August
Best forWaterfront stays
Featured32 rentals
The curated list · 32 rentals
Where we would stay in Hilton Head Island.
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No. 02
Luxurious Ocean Front Home w/ Rec Room
Oceanfront
8 bedroom
sleeps 32
Discover paradise at this top rated beach location with luxury amenities and spacious living areas.
No. 03
Private Island in Hilton Head, Events & Poolside
On the beach
8 bedroom
sleeps 26
Accommodating up to 26 guests, this luxurious sanctuary is perfect for creating unforgettable memories with family and friends.
No. 04
Spectacular Oceanfront 8 Bedroom Palmetto Dunes Home with Private Balconies
Oceanfront
8 bedroom
sleeps 24
This guest mansion on Hilton Head boasts eight bedrooms, all with private full baths, and is perfect for extra large groups, providing direct access to the beach and sea.
No. 05
31 Singleton Beach- Oceanfront luxury home, spectacular views & private pool, FREE Activities Included
House
7 bedroom
Oceanfront
private pool
The entire place is yours with beachfront location and a private pool.
No. 06
6 Terra Bella Trace- Oceanfront, Elevator, Private Pool, Roof Top, FREE Activities Included
Home
7 bedroom
sleeps 14
Beachfront
private pool
6 Terra Bella Trace in Hilton Head Island offers direct beachfront access with stunning ocean views.
No. 07
3 Singleton Beach - Oceanfront Estate, Private Pool, Elevator, FREE Activities Included
Estate
7 bedroom
sleeps 14
Beachfront
private pool
7 bedrooms and 7 bathrooms with private pool and beachfront access.
No. 08
20 Horvaths Peninsula- Oceanfront, Pets OK, Great Location, Free Activities Included
House
6 bedroom
Beachfront
private pool
The entire place is yours, featuring 6 bedrooms, 5 bathrooms, and private amenities.
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32
curated rentals in Hilton Head Island
No. 09
Daufuskie Oasis 6BR Family Home - Beachfront
Vacation Home
6 bedroom
Beachfront
private pool
Daufuskie Oasis 6BR Family Home - Beachfront offers direct beachfront access with stunning sea views.
No. 10
Oceanfront, Sea Pines, Pool & Private Beach Access
House
6 bedroom
sleeps 12
Beachfront
private pool
Beachfront location with direct access and a private pool.
No. 11
12 Collier Beach, Oceanfront, Pool, Great for Large Groups, Free Golf, Oceanfront
Oceanfront
6 bedroom
sleeps 16
12 Collier Beach Rd in Hilton Head is a wonderful oceanfront home, perfect for a vacation getaway with private beach access and stunning ocean views.
No. 12
11 Singleton Beach by AvantStay | Oceanfront Retreat w/ Private Pool + Boardwalk
Oceanfront
6 bedroom
sleeps 12
Experience the ocean as your backyard with this six-bedroom, six-bath coastal retreat located directly on Singleton Beach.
On the water
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No. 13
Luxury Oceanfront Home in North Forest Beach!
Oceanfront
6 bedroom
sleeps 14
This breathtaking 6-bedroom, 6½ bathroom direct oceanfront vacation home in North Forest Beach boasts a private pool, fabulous ocean views, and is just steps away from the beach.
No. 14
Exclusive Pool and Five Unique Apartments - Stunning Beachside Villa
Villa
9 bedroom
sleeps 28
private pool
Welcome to Beachside Villa a Large Group Retreat with Private Pool The quintessential location, the ideal large group accommodation and a perfect place to reset your clock from workaday to leisure time, Beachside Villa has it all. What's more, this unique example of Tybee Island vacation homes is newly refurbished and sparkling clean. If you have been thinking about getting everyone in the family together for a reunion or treating the office staff to a fabulous retreat, there is no time like the present to put the wheels in motion. With five self-contained apartments and room for up to 28 guests, this gem among vacation rentals Tybee Island GA is a rare find indeed.
No. 15
Heated Pool and Spa with Private Beach Access - Stunning Oceanfront Escape
House
8 bedroom
sleeps 19
private pool
HOST & HOME presents… - an exquisite 5,000 sqft+ oceanfront escape in South Forest Beach designed for your sophisticated taste! Stroll your private boardwalk to the beach, sink into the heated pool or spa, and take in endless ocean views. This 8-bedroom sanctuary for up to 19 guests is perfect for connection and comfort. Share stories by the firepit, retreat to the serene guest house, or simply unwind on expansive decks. Escape the rush, embrace the calm, and create unforgettable memories. Learn more below… HIGHLIGHTS Prime Oceanfront Location: Direct beach access via a private boardwalk in stunning South Forest Beach. Spacious Design for Large Groups: 8 luxurious En-Suites across 5,226 sq.
No. 16
Oceanfront Paradise with Pool and Spa - Stunning Coastal Retreat
House
7 bedroom
sleeps 26
private pool
Here at Vacation Rentals we believe in providing you with amenities you won't find anywhere else. The following are included for your comfort, convenience, and enjoyment: 1. Luxury bedding/Bath & Beach Towels 2. Ping Pong Table, Foosball, Cornhole, Pac-Man Arcade Game 3. Private Pool & Spa (can be heated for an additional fee) 4. Poolside Bathroom 5. Grill and Propane tank for outdoor cooking 6. Outdoor Bar and Dining 7. Hair dryers in each bathroom 8. Wifi 9. 6 Backpack Beach Chairs and a beach wagon 10. We offer both a drip coffeemaker and Keurig 11. Baby Gear: pack and play (sheets are not provided), high chair and umbrella stroller.
Coastal craftsmanship
Bags made from recycled sails. Handcrafted in Maine.
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No. 17
Massive Luxury Beach Home Private Pool Hilton Head
House
6 bedroom
sleeps 18
private pool
8 Nighthawk, Experience the ultimate luxury at this stunning 6-bedroom beachfront home in Hilton Head, perfect for up to 18 guests. Indulge in 5.5 bathrooms, a private pool and spa, and a tiki bar. Whether you prefer lounging in the rec room or soaking up the sun on the nearby beach, this home offers an unforgettable vacation experience. Book today and enjoy a vacation reimagined with the property manager, your trusted partner in Hilton Head Island Property Management. Some vacations are about getting away. Others are about bringing everyone together without giving up space, comfort, or style.
No. 18
Expansive Backyard Oasis and Upper Sun Terrace - Exquisite Coastal Retreat
House
6 bedroom
sleeps 14
private pool
Welcome to South Beach Serenity, your luxurious beachfront haven on Hilton Head Island. This stunning retreat invites you to bask in the serenity of sun-soaked days and ocean breezes. Step into the expansive backyard oasis, where a private pool beckons, surrounded by a spacious patio. For those seeking elevated relaxation, ascend to the upper sun terrace, which is equipped with loungers that provide a perfect vantage point for absorbing ocean views. Inside, the main living area is a vision of openness and light, with floor-to-ceiling windows framing the beauty of the sea.
No. 19
Spacious Home with Pool and Spa - Elegant Coastal Retreat
House
6 bedroom
sleeps 16
private pool
Welcome to 5 Junket, a family-friendly retreat for up to 16 guests in Palmetto Dunes Oceanfront Resort. With Peek-a-Boo Ocean Views and just 37 steps to the beach, it's perfect for multi-family gatherings or friends' getaways. This spacious home offers 6 en-suites, a luggage elevator, a large private yard with pool and spa, and an 1100+ sqft wrap-around deck surrounded by Lowcountry greenery. Stone's throw to golf, tennis, and more resort amenities. Discover Hilton Head Island with us. Learn more below! HIGHLIGHTS 6 Bedrooms, 6 Full and 1 ½ Bathrooms across 2 levels, sleeping up to 16 guests: 4 King en-suites, 1 Guest room with 2 Twins and 1 Bunk room with 4 Twins and a sleeper sofa.
No. 20
Luxury Pool and Spa Oasis - Stunning Oceanfront Escape
House
6 bedroom
sleeps 14
private pool
HOST & HOME presents…. Your beachfront escape in South Forest Beach! The centerpiece of this home is its luxurious outdoor oasis, designed for relaxation and unforgettable moments. Unwind in the pool and spa, soak up the sun on the deck, and take a serene stroll down the wooded path to the beach. With a propane grill and scenic seating areas, it's the perfect setting for alfresco dining. You'll feel like a VIP on your own private escape. The ocean is calling!
No. 21
Private Pool, Outdoor Hot Tub, Gourmet Kitchen - Stunning Retreat
House
6 bedroom
sleeps 12
private pool
Here at Vacation Rentals we believe in providing you with amenities you won't find anywhere else. The following are included for your comfort, convenience, and enjoyment: 1. Luxury bedding used by the Ritz Carlton/Bath & Beach Towels 2. Outdoor Hot Tub 3. Private Pool (can be heated for an additional fee) 4. Propane tanks for grilling 5. Beverage Refrigerator and Deep Freezer 6. Hair dryers in each bathroom 6. Wifi and smart tv's (streaming only) 8. 6 Backpack Beach Chairs and a beach wagon 9. We offer both a drip coffeemaker and Keurig Oceanfront Sea Pines Luxury.
No. 22
Luxurious Oceanfront Haven with Huge Pool and Entertainment Area - Exquisite Retreat
House
6 bedroom
sleeps 24
private pool
Here at Vacation Rentals we believe in providing you with amenities you won't find anywhere else. The following are included for your comfort, convenience, and enjoyment: 1. Luxury bedding/Bath & Beach Towels 2. Ping Pong Table, Cornhole, Foosball, Shuffleboard 3. Private Pool & Spa (can be heated for an additional fee) Lap Pool Section 39'x9'. Swimming Pool Section including spa 37' x 21' Pool depth is 3ft - 5ft 4. Grill and Propane tank for outdoor cooking 5. Outdoor Bar with wine cooler 6. Hair dryers in each bathroom 7. Wifi 8. 6 Backpack Beach Chairs and a beach wagon 9. We offer both a drip coffeemaker and Keurig 10.
No. 23
Oceanfront Access and Stunning Views - Amazing Coastal Escape
House
7 bedroom
sleeps 20
private pool
This oceanfront stunner was built in 2019 and offers amazing views as well as direct access to the beach with a private boardwalk. Walk into an amazing great room to unwind from a day out in the sun. The living room has two couches and two comfy chairs that leads out to the first balcony to soak in the picture-perfect view of the ocean. The kitchen is completely stocked with everything you need, and there is plenty of counterspace on the huge kitchen island for many people to cook simultaneously with room to spare. There is seating for 14 at the dining table and 3 stools at the kitchen bar. The main level of the home also contains a powder room and two bedrooms.
No. 24
Heated Pool Access and Spacious Living - Stunning Family Retreat
House
6 bedroom
sleeps 15
private pool
in Savannah, GA, and Tybee Island, GA provides first-class amenities including access to our exclusive resort-style heated pool located at 19 Silver Avenue, Tybee Island GA. All of our homes are professionally cleaned after each stay, and disinfected using a quaternary disinfectant throughout the entire property prior to each new arrival. One of Southern Belle's newest Tybee vacation homes is a 2400 sq foot pristine home located steps from Tybee's beach. Featuring a six bedroom home with 5 full bathrooms. This Tybee vacation home will comfortably sleep 15. It features several amenities that will benefit a large family or group.
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No. 25
Oceanfront Oasis with Private Pool and Spa - Elegant Getaway
House
8 bedroom
sleeps 20
private pool
welcome to 9 guscio- newly renovated and outlined with elegance in every detail, this 3-story oceanfront home is truly perfect for your next hilton head island family getaway. this home has an extremely open floor plan that allows an easy flow between the living room, kitchen, and dining area. the living room is well-appointed and spacious, and natural light fills every corner in the room through the large windows. there is plenty comfortable seating for everyone to enjoy, and a large flatscreen tv for your entertainment. in the kitchen, there is plenty of walkway and counterspace to allow multiple people to cook simultaneously without feeling crowded.
No. 26
Private Pool and Glorious Ocean Views - Exquisite Beachfront Haven
House
8 bedroom
sleeps 21
private pool
With a private pool, eight bedrooms, and glorious ocean views, this massive Sea Pines beach house is perfect for group getaways. Welcome to this distinctive vacation property managed locally. The property is situated among the palmettos and oak trees of Hilton Head Island and steps away from the Atlantic Ocean. The lapping of the waves on the beach of this oceanfront home will put you to sleep, while the bedrooms on the street side of the house get a peek at the lagoon across the way. This luxury home is near the southern tip of the island and a short drive from the Salty Dog Cafe and other popular spots.
No. 27
In-Ground Pool and Ocean Views - Elegant Beachfront Retreat
House
8 bedroom
sleeps 26
private pool
Make your next vacation one to remember with this beautiful home in Sea Pines. 23 Black Skimmers modernist style offers the perfect atmosphere for relaxation and entertainment. Welcome to this distinctive vacation property managed locally. This 7,500-square-foot beachfront home features a private, in-ground pool with a spa and a patio overlooking the Atlantic Ocean. With private beach access, this home is perfect for those long beach days! The kitchen is equipped with stainless steel appliances, a split, two-sink granite island set, and ample countertop space, so there's plenty of room to cook delicious meals and easy cleanup with two dishwashers.
No. 28
Luxury Home w/Pool & Spa Near Beach on Hilton Head
House
6 bedroom
sleeps 14
private pool
39 Off Shore - This stunning 6-bedroom, 5-bathroom home in Palmetto Dunes boasts a beautiful expansive deck, private pool, and hot tub with serene and secluded views. The perfect retreat for families or groups of friends looking for a luxurious and comfortable vacation. Enjoy sunbathing and relaxing by the pool during the day, and stargazing from the hot tub at night. This home offers the ultimate combination of privacy, comfort, and elegance. Find yourself at home in this beautiful 6-bedroom home on a peaceful street in Palmetto Dunes with a private pool, hot tub, and everything you need for your next Hilton Head vacation!
No. 29
Ocean Access and Private Pool - Stunning Coastal Sanctuary
House
6 bedroom
sleeps 18
private pool
this oceanfront home is newly updated and offers direct access to the beach as well as an expansive outdoor entertainment area that is sure to be your favorite spot for summer days! upon entry, you walk into the home's sitting room which has a dining table for 4 and comfortable seating that is perfect to unwind on over your favorite novel. take a few more steps into the massive great room and take in one of the most amazing views on hilton head- the huge windows along with the high ceilings truly help capture an amazing view of the atlantic ocean. there is plenty seating for all around the flatscreen tv on the large sectional and additional chairs if needed.
No. 30
Oceanfront Pool and Beach Access - Exquisite Family Retreat
House
8 bedroom
sleeps 24
private pool
There is no need to look any further than oceanfront Beachside Bliss for your next family reunion or getaway, as this one-of-a-kind, 8,000-square-foot luxury home will spoil everyone lucky enough to come along. Welcome to this distinctive vacation property managed locally. There is no need to look any further than oceanfront Beachside Bliss for your next family reunion or friends’ getaway, as this one-of-a-kind, 8,000-square-foot luxury home will spoil everyone lucky enough to come along! As soon as the sun comes up, your days will be filled with island fun in the oceanfront pool with a spa and a hot tub. A few feet away, the private beach access will be the cherry on top for beach lovers.
No. 31
Ocean and Marsh View Home with private pool, dog friendly, beachfront
House
6 bedroom
sleeps 16
private pool
Collier Court 4 Welcome to your dream getaway in Hilton Head, SC! Just 50 feet from the beach path, this stunning house offers breathtaking views of both the ocean and marsh, making it the perfect retreat for families and friends. With 6 spacious bedrooms and 6.5 bathrooms, each equipped with its own private bathroom, everyone can enjoy their own space while still being together. The residence boasts three ocean-view porches where you can sip your morning coffee or unwind with a glass of wine as the sun sets. Dive into the heated private pool for a refreshing swim or challenge your loved ones to a game of ping pong. The home is dog-friendly, so your furry companions can join in on the fun!
No. 32
Stunning oceanfront home with pool, private boardwalk, decks, & elevator
House
6 bedroom
sleeps 16
private pool
Dune Lane 105 If you’ve been planning a group getaway to Hilton Head but haven’t yet found the perfect place, stop scrolling - here it is. With an unbeatable oceanfront location just two miles from Coligny Beach Park, beach access via your own boardwalk, two enormous wraparound decks, a pool, and stunning ocean views from the main areas of the home, you’ll feel like you’ve stumbled into your own private paradise. Thoughtful upgrades include a remodeled kitchen with all new top-of-the-line appliances, new countertops, and brand-new cabinets.
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