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
Featured41 rentals
The curated list · 41 rentals
Where we would stay in Hilton Head Island.
Affiliate links. About our partners.
No. 02
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. 03
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. 04
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. 05
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.
No. 06
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. 07
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. 08
Waterfront Escape - Seasonal Pool - Perfect for Families and Friends!
Five-Bedroom House
5 bedroom
Beachfront
private pool
Beachfront location with direct access and stunning sea views.
Browse more in Hilton Head Island
Search every rental in Hilton Head Island.
Filter by dates, bedrooms, price, and distance to water. These are the full Vrbo and Booking.com inventories for Hilton Head Island.
41
curated rentals in Hilton Head Island
No. 09
5 Sea Oak Lane
Home
5 bedroom
sleeps 12
Steps to Beach
private pool
Spacious holiday home with five bedrooms and four bathrooms.
No. 10
Paradise
Vacation Home
5 bedroom
sleeps 14
Beachfront
private pool
Beachfront Location: Paradise in Hilton Head Island offers direct beachfront access with stunning sea views.
No. 11
8 Seaside Sparrow
Home
5 bedroom
sleeps 22
Steps to Beach
private pool
8 Seaside Sparrow in Hilton Head Island offers spacious accommodations with five bedrooms, seven bathrooms, a private pool, and is just a few steps away from South Beach.
No. 12
Direct Beach Path & Pool Near The Salty Dog Cafe
Holiday Home
5 bedroom
sleeps 12
Beachfront
private pool
Spacious holiday home with five bedrooms and six bathrooms, featuring a private pool.
On the water
Affiliate link.
No. 13
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. 14
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. 15
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.
No. 16
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.
Coastal craftsmanship
Bags made from recycled sails. Handcrafted in Maine.
Shop Sea Bags →Affiliate link.
No. 17
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. 18
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. 19
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. 20
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. 21
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. 22
Private Pool and Spa with Outdoor Kitchen - Luxurious Family Retreat
House
5 bedroom
sleeps 14
private pool
brand new construction 3rd row home in palmetto dunes! 5-bath luxury home nestled in the beautiful palmetto dunes oceanfront resort. just 3 rows from the beach, this home is meticulously designed for your perfect vacation. with an open first floor layout, the entire family can spread out without missing out on all the fun activities. the brand-new chef’s kitchen features top of the line, stainless steel appliances. it is fully stocked with every tool you may need for delicious gourmet meals. just off the main living space are two spacious bedrooms, each with a private en-suite bathroom, as well as a private office for the perfect “work from anywhere” set-up.
No. 23
135 Mooring Buoy
House
5 bedroom
sleeps 14
private pool
Stunning Pet Friendly Lagoon Front Home with Private Pool and Spa, 4th row from the beach Welcome to this distinctive vacation property managed locally. Welcome to this stunningly renovated fourth row beach home in the heart of Palmetto Dunes, where luxurious indoor living, resort-style outdoor spaces, and breathtaking lagoon views come together on an oversized double lot just moments from the beach. Guests will also enjoy access to Palmetto Dunes amenities, including miles of bike paths, world class golf, tennis, pickleball, dining, and more. As you arrive, the home immediately makes a statement with dual staircases leading up to the grand front entrance.
No. 24
Oceanfront 5BR, Private Pool, Sleeps 13, Upper Balcony Views, in Forest Beach
House
5 bedroom
sleeps 13
private pool
Welcome to…! This stunning oceanfront escape in North Forest Beach blends modern coastal luxury with breathtaking Atlantic views, spacious open-concept interiors, and direct private beach access. Spend your days relaxing by the private pool and spa, gathering in beautifully designed living spaces, and enjoying effortless indoor-outdoor living just steps from the sand. With upscale furnishings, a gourmet chef's kitchen, and thoughtful vacation perks throughout, is designed for unforgettable Hilton Head Island getaways! Learn More Below!
Curated luxury alternative
Prefer a boutique hotel?
Design-led hotels and villas via Skylark Travel Group. Mr & Mrs Smith properties, exclusive deals, real human concierge.
Sponsored
No. 25
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. 26
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.
No. 27
Oceanfront Home with Private Pool and Hot Tub - Stunning Coastal Retreat
House
5 bedroom
sleeps 16
private pool
this oceanfront home is in north forest beach. soak in the amazing views as soon as you walk in. grab a seat in the living room or outside on the patio to listen to the waves. right off the living room is the kitchen that has seating at the breakfast bar for 4 and a dining table for 12. head upstairs where the bedrooms are located. the first two bedrooms each have a king bed and sofa pull out. the next two rooms has a king bed. the final bedroom has two full beds. each bedroom has their own bathroom with a walk-in shower. the master bathroom features a large tub. downstairs along with a private pool and hot tub is a lounge area. the lounge area features seating, a wet bar, and a pool table.
No. 28
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. 29
Expansive Living Areas and Dual Entrances - Stunning Coastal Haven
Villa
5 bedroom
sleeps 14
private pool
This expansive property features five bedrooms and two separate entrances, providing ample space and privacy for larger groups. This property boasts multiple living areas, ensuring plenty of room for everyone to spread out and relax. Welcome to this distinctive vacation property managed locally. This expansive property features five bedrooms and two separate entrances, providing ample space and privacy for larger groups. This property boasts multiple living areas, ensuring plenty of room for everyone to spread out and relax. This amazing villa features two fully equipped kitchens with modern appliances, ample counter space, and all the necessary cookware and utensils.
No. 30
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. 31
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. 32
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!
Still looking?
Search the full inventory.
Our curated picks are just the start. Browse hundreds more rentals in Hilton Head Island by date, price, and size.
No. 33
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. 34
Private Pool and Spa Oasis - Spacious Family Retreat with Entertainment
House
5 bedroom
sleeps 22
private pool
HOST & HOME presents… 24 Cartgate. Escape to this pet-friendly retreat in Palmetto Dunes Oceanfront Resort, Hilton Head, where unforgettable memories await. Perfect for up to 22 guests, enjoy a private pool, spa, and spacious backyard under the warm Carolina sun. A cozy loft with a foosball table and video console ensures quality time for everyone. With beaches, golf, and endless adventures just a 10-minute walk away, this home is your ultimate oasis. Ready to explore? Learn more below. HIGHLIGHTS Private Retreat for Large Groups: Spacious home accommodating up to 22 guests featuring multiple bedrooms. Pet Friendly: Bring your furry dog!
No. 35
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. 36
10 Cassina Lane
House
5 bedroom
sleeps 12
private pool
Charming Completely Renovate 5 bedroom/4.5 bathroom oceanfront with private pool and boardwalk to the beach Welcome to this distinctive vacation property managed locally. This stunning, brand-new property was just completed in June 2025 and is ready to welcome its very first guests! The heart of the home lies upstairs, where the main living room impresses with vaulted ceilings and a wall of windows that flood the space with natural light. A plush sectional, coffee table, and accent chairs create a stylish, inviting area that flows into the dining space. The large wood table seats eight and is surrounded by woven-back chairs and open shelving.
Coastal craftsmanship
Bags made from recycled sails. Handcrafted in Maine.
Shop Sea Bags →Affiliate link.
View all 41 waterfront rentals in Hilton Head Island ↓
No. 37
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. 38
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.
No. 39
Stunning Oceanfront Hideaway with Private Pool, Deck, and Yard - Dogs Welcome
House
5 bedroom
sleeps 14
private pool
Paradise *Please read our important pool heat information to help you have the best vacation possible!* This property has a pool that can be heated between Labor Day and Memorial Day for an additional fee of $69/night. You MUST notify management at least seven days in advance of your arrival if you would like to purchase pool heat. If the outside temperature is colder than 55 degrees, the pool will not be able to maintain a warmer temperature. If the pool does not reach your desired temperature but is still warming, refunds will NOT be given. Enjoy the tropical landscape and the first floor elevated balcony ocean views, which span the entire width of this dog-friendly home.
No. 40
Beachfront beauty with pool access fireplaces, jetted tub, balconies, & WD
House
5 bedroom
sleeps 10
shared pool
Sea Pointe This elegant five-bedroom home is just steps away from Singleton Beach and the shared community pool! Bring the whole family and create sun-soaked, lifelong memories in Hilton Head. When your toes aren't dug into the warm white sand, check out Folly Field Beach Park, the Arts Center of Coastal Carolina, the Coastal Discovery Museum, the Harbour Town Lighthouse, and Harbour Town Golf Links. When you're ready to relax, your home away from home will welcome you with open arms! Kick up your feet and tune into your favorite TV shows and movies in the spacious living room. When extra warmth is needed, turn on the gas fireplace.
Booking.com
Hotels, beach houses & apartments in Hilton Head Island.
Browse on Booking.com →Affiliate link.
No. 41
Beachfront home with private pool, expansive deck & breathtaking views
House
5 bedroom
sleeps 12
private pool
Dunes House Enjoy life at the beach at Dunes House! This home has impressive views of the beach and the Atlantic Ocean. The open living space on the second floor has living, dining, and a well-equipped kitchen that all look out to the Atlantic. Enjoy a cookout on the large deck off of the second floor or unwind on the screened porch. The first floor has a second living area leading out to the pool that can be heated for an additional fee. Surf and sand are a few steps away using the beach path next to the home. The modern Coligny Beach Park area provides benches, swings, restrooms, and changing rooms for beachgoers.
Curated luxury alternative
Prefer a boutique hotel or villa?
If a hand-picked, design-led hotel sounds better than a vacation rental, Skylark Travel Group covers the same destinations with curated boutique stays, Mr & Mrs Smith, exclusive deals, real human concierge.
Sponsored.
Before you book
Get new waterfront rentals as we add them.
Hand-picked for genuine waterfront. New finds and off-season picks, sent when there is something worth sending. No spam.
Other waterfront towns
