Vacation Home Rentals By Owner In Hilton Head Island, SC

184 Mooring Buoy | Golf Course Views | Short Walk to the Beachbrbr***Newly Renovated for 2025***brbr*5 Bedrooms | 4 Bathroomsbr*Sleeps 12br*2 Kings, 2 Queens, 2 Pyramid Bunk Bedsbr*Short Walk to the Beach br*Pup- Friendlybr*Back Deck Overlooks Lagoon and Robert Trent Jones Golf Coursebr*Enjoy Daily Rounds of Golf & Children's Activities with this Home br*Beach Gear Credits Included br*4 TV's | DVD | Alexa | WiFi | Keurig | Gas Grillbr*Private Pool {Pool Size 28' x 12'}br*8 Beach Towels for Guest Usebr*Keyless Entry br*Access to the Palmetto Dunes Buggy (seasonal)br*5 Car Maximum | *No Parking on the StreetbrbrWelcome to 184 Mooring Buoy!brbrTucked among lush, manicured landscaping, 184 Mooring Buoy invites you to experience the ultimate island getaway. This beautifully appointed 5-bedroom, 4-bathroom vacation home blends coastal charm with modern comfort, all just a short stroll from the beach.brbrAs you step inside, soft blue walls and crisp white trim immediately create a sense of calm. Natural light pours into the cozy living room through a wall of windows, offering stunning views of the Robert Trent Jones Golf Course, a serene lagoon, and your private backyard oasis with a sparkling pool. Gather around the plush seating area or enjoy meals in the adjacent dining room, which comfortably seats eight.brbrThe recently renovated kitchen is a chef’s dream, featuring elegant marble countertops, high-end stainless steel appliances, and a spacious breakfast bar with seating for six.brbrOn the main floor, you’ll find three well-appointed bedrooms. Located near the entry, this welcoming room features a queen bed, 32” TV, and a private en-suite bathroom with a tub/shower combo. The master bedroom is a spacious retreat with a king bed, 48” TV, large walk-in closet, and sweeping views of the lagoon and golf course. The luxurious en-suite bath includes a soaking tub, walk-in shower, and dual vanities. Tucked behind the kitchen is the third guest room. This inviting room offers a king bed and convenient access to a nearby full bathroom with a walk-in shower.brbrUpstairs, two additional guest rooms provide flexible sleeping arrangements for families or larger groups. The first room is a fun and functional space for kids or teens, featuring two pyramid bunk beds (twin over full), a TV, and an en-suite bathroom with a tub/shower combo. Bright and cozy, the second upstairs room includes a queen bed and a TV, offering a peaceful place to unwind.br brStep outside to your private outdoor haven, where you'll find six lounge chairs, a Weber propane grill, and a patio table with seating for eight—perfect for alfresco dining, sunbathing, or simply enjoying the views of the fairway.brbrWhether you're enjoying a quiet morning coffee by the pool, walking to the beach, or watching golfers from the backyard, 184 Mooring Buoy is your home away from home in paradise.brbrDIRECTIONS TO THE BEACH: From your property, take a left on Mooring Buoy towards the beach access path at Night Harbor.brbr*Pool can be heated March – October only for an additional feebr{If the outside temperature is colder than 55 degrees, the pool may not be able to maintain a warmer temperature. If the pool does not reach the desired temperature but is still warming, refunds will NOT be given}br*4 Night Minimum Stay Required. Summer Rentals Weekly Only (Sat. to Sat.)br*Property May Be Monitored by Exterior Security Cameras

184 Mooring Buoy ~ Enjoy Peaceful Golf Course Views & Short Walk to the Beach |

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$893.42

Summary:brbrTucked beneath moss-draped oaks in the heart of Sea Pines, 57 Lawton Road is a serene Lowcountry retreat with a private pool and spa surrounded by lush greenery. Inside, soaring ceilings and sun-filled living spaces flow into a stylish kitchen and inviting gathering areas. Step outside to a tranquil lanai and pool deck perfect for relaxing days and starry nights. Close to beaches, golf, and trails, this pet friendly home offers the perfect Hilton Head escape.brbrbrbrThe Space:brbrTucked beneath a canopy of moss-draped oaks in the heart of iconic Sea Pines, 57 Lawton Road immediately captures your imagination as the kind of Lowcountry retreat guests dream about long after they leave. From the moment you arrive, the setting feels serene and private, with lush greenery surrounding an inviting backyard oasis that features a beautifully designed pool and attached spa. Sunlight filters through the trees, reflecting off the water and creating a peaceful, resort-like atmosphere that feels worlds away from everyday life. Perfectly positioned close to beaches, golf, biking trails, and all the best of Hilton Head Island, this home offers both convenience and a secluded escape designed for unforgettable vacations!brbrbrbrStep inside and you are greeted by expansive open living spaces filled with gorgeous natural light pouring in through two stories of windows that rise to cathedral ceilings. The living area is both stylish and comfortable, featuring oversized sofas perfect for lounging, a large smart TV for movie nights, and two plush recliners positioned in front of a soaring decorative fireplace* that anchors the room. The kitchen and dining area flow seamlessly from the living space, showcasing wide slab granite countertops, stainless steel appliances, and a generous center island that makes cooking and entertaining a joy. With bar seating for four and vibrant dining chairs and bench seating, this space was made for shared meals, laughter, and late night conversations after a day of island adventures.brbrFour guest rooms continue to express the best of Lowcountry living amid marvelously updated surroundings. The first of three on the ground floor could function as a main suite, with its sprawling California king-size bed set beneath a ceiling fan and spacious en-suite bathroom with dual-basin vanity, expansive walk-in shower and separate tub. A few steps across the foyer, you'll find another pair of bedrooms. One has a full bath with a spacious walk-in shower. There is also another full bath beside these rooms. King beds in both rooms with plenty of space to relax and unwind. Both include a work desk space. The final bedroom can be perfect for the kids with 4 brightly colored oversized twin beds as well as a beautiful and comfortable king bed. This room also provides a space to play games which are provided and space for the kids, both young and old.brbrbrbrGlass doors invite you into a seamless indoor-outdoor living experience, opening onto a spacious lanai that overlooks a tranquil conservation area where nature sets the tone for total relaxation. From here, gentle steps lead down to your private pool deck, where a sparkling pool and bubbling spa create a secluded retreat surrounded by lush bamboo and native Lowcountry trees. Mornings begin with coffee in the shade, afternoons drift by as you lounge poolside after a beach day made easy with provided chairs, boards, and a wagon, and the spa becomes the perfect place to unwind as the day slows. As evening settles in, the pool glows softly, offering one last refreshing dip or a peaceful soak beneath the stars before heading inside to cozy up by the fireplace. Designed for effortless vacation living, 57 Lawton Road blends adventure, relaxation, and comfort into a pet friendly coastal escape you will want to return to year after year! Enjoy a vacation reimagined with host2coast, your trusted Hilton Head Island Property Management partner.brbrbrbrbrbrPROPERTY SPECIFIC DETAILS:brbrbrbr* Sea Pines is a gated community in which every vehicle must have a gate pass for entry. One gate pass is included with your reservation at the time of booking. If you require additional passes, please request the exact number needed to ensure they are prepared in advance. Each pass has a fee of $17. All gate passes must be picked up at the host2coast office prior to entry.brbr* Dog Friendly - 2 dog max. $250 non-refundable fee per dog. Dogs are not permitted on the furniture and must be crated if left alone. Please do not leave furry friends alone outside, as we have wildlife that they should not encounter.brbr* Pool and/or spa heating is available for an additional fee and can be arranged after your booking is confirmed. We kindly ask that heating is ordered in advance of the stay. If the outdoor temperature falls below 60 degrees, the pool heater may not function properly and the pool may not reach the desired temperature. Please note that no refunds will be issued if the pool heating equipment cannot maintain the temperature.brbr* Due to safety concerns, the fireplace is not available for guest use.brbrbrbrSTR Permit # 76270brbrbrbrGuest Access:brbrAccess codes are provided just prior to your arrival and auto-generated for each booking. You can also find your code in our Guest App. Keyless entry, no contact check-in and checkout.brbrbrbrThe Neighborhood:brbrSea Pines has a variety of family and individual activities including natural beaches, championship golf, tennis, biking trails and so much more.brbrbrbrGetting Around:brbrBiking is very popular on Hilton Head Island, known for the many award-winning trails. There are recommendations for bike rental companies within your Guest App. You can reserve in advance and they will deliver to you or bring your own! Almost everything you will need is within walking distance, so bring your walking shoes! Sea Pines provides a complimentary seasonal trolley service that helps guests and residents travel around the resort without using a car. The trolley connects major destinations such as Harbour Town, the Sea Pines Beach Club, South Beach Marina, and The Shops at Sea Pines Center, making it easy to access beaches, dining, and shopping throughout the community.

Hidden Sea Pines Gem | Pool, Spa, Pet Friendly

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$984.95

Summary:brbrWilloughby House is a newly built luxury coastal retreat just a 3-minute walk from the beach. This spacious 4-bedroom, 3.5-bath home features designer coastal interiors, a gourmet chef’s kitchen, elegant dining for 10+, and a refined family room with fireplace and TV. Enjoy a main-level primary suite, multiple indoor and outdoor living spaces, resort-style amenities, and seamless beach access—perfect for upscale family and group getaways.brbrbrbrThe Space:brbrRefined Coastal Retreat Steps from the BeachbrbrbrbrWhy Guests Love This Homebrbr• Unbeatable Location – Just a 3-minute walk to the beach, offering effortless access to the shore without sacrificing privacy.brbr• Brand-New Custom Build – Thoughtfully designed with upscale finishes and coastal elegance throughout.brbr• Spacious & Private Layout – Four beautifully appointed bedrooms, including a main-level primary suite and separate upstairs living area.brbr• Gourmet Chef’s Kitchen – Professional-grade oven, 6-burner stovetop, walk-in pantry, and coffee station—perfect for entertaining.brbr• Exceptional Gathering Spaces – Open-concept living, dining for 10, bar seating, and multiple indoor and outdoor lounge areas.brbr• Resort-Style Amenities – Covered porch with TV, outdoor dining, outdoor shower, and garage game area with ping-pong and foosball.brbr• Beach-Ready Convenience – Beach chairs, beach towels and wagon provided for seamless beach days.brbr• Ideal for Work & Play – Dedicated office space and washer/dryer on both levels for added comfort and convenience.brbr•. Option to rent a Yukon XL Denali as an add on.brbrWelcome to Willoughby House, a newly constructed custom coastal home designed for guests seeking space, style, and effortless beachside living. Located just a 2-3 minute walk from the beach, this thoughtfully curated 4-bedroom, 3.5-bathroom residence offers upscale comfort in a serene coastal setting.brbrbrbrElevated InteriorsbrbrFrom the moment you enter, you’ll notice the attention to detail—coastal-inspired color palettes, high-end finishes, and an open, airy layout ideal for entertaining and relaxing alike.brbrThe main living area features a sophisticated family room with a fireplace and a large HiSense TV, creating a cozy yet refined atmosphere. Adjacent is a beautifully appointed dining space with seating for 10, complemented by additional bar seating for 4, perfect for hosting elegant dinners or casual gatherings.brbrThe chef’s kitchen is a standout, equipped with a professional-grade oven, 6-burner stovetop, walk-in pantry, and a dedicated coffee station—designed to meet both gourmet and everyday needs.brbrbrbrPrivate & Thoughtful Sleeping ArrangementsbrbrThe primary suite on the main level offers a peaceful retreat with a spa-like ensuite bathroom. Also on the main level is a private office, ideal for remote work or quiet moments.brbrUpstairs, guests will find three beautifully appointed bedrooms and a refined sitting lounge with a TV:brbr• Bedroom 2: Two twin beds with trundles (sleeps 4)brbr• Bedroom 3: King bedbrbr• Bedroom 4: King bedbrbrFor ultimate convenience, washer and dryer units are available on both levels.brbrbrbrResort-Style Outdoor LivingbrbrEnjoy multiple outdoor spaces designed for relaxation and entertainment:brbr• Covered first-level porch with TV, perfect for evening unwindingbrbr• Ground-level outdoor dining area with seating for 6brbr• Private outdoor shower for post-beach refreshmentbrbr• Outdoor grill (will be available starting in April)brbrGuests are provided with 6 beach chairs and a beach wagon, making beach days seamless. The garage offers elevated entertainment with a ping-pong table and foosball table, adding a touch of resort-style fun.brbrbrbrGuest Access:brbrYou can access the home through the main front door. You will also have access to most spaces in the garage. (please no parking in the garage) The entire main level and 2nd floor are yours to enjoy!brbrbrbrThe Neighborhood:brbrJust steps from the sand, Willoughby House offers easy access to the beach while still providing a peaceful, private retreat to come home to. The Willoughby House is near the back entrance of Sea Pines and also close proximity to Coligny Plaza where there is lot of shopping and restaurants.brbrbrbrGetting Around:brbrGetting around Hilton Head Island is easy and enjoyable from this location. The home is just a short walk or bike ride to the beach, with scenic leisure paths nearby for walking, biking, or jogging. Guests can easily explore Sea Pines, Harbour Town, and local shops and dining by bike, car, or the island’s seasonal trolley service. Coligny Plaza—home to popular restaurants, boutiques, and live entertainment—is just a short drive or bike ride away. Parking is provided at the home for added convenience.brbrbrbrOther Things to Note:brbrTOWN OF HHI STR PERMIT NO. 077438brbrbrbrPlease note the the hot water rest from 12AM to 6AM and will not be available.brbrbrbrWe provide streaming services on the Smart TV's where you can sign in to your favorite app. There is no Cable TV. brbrAlso there are 3 TV's-the TV's are located in the main family room, the 2nd level sitting area, and outside on the porch.brbrbrbrThere are security cameras in the front facing the porch and in the back facing the back porch upper and lower.brbrbrbrThe grill will be not be available until April 2026.brbrbrbrNo parking in the garage, please.brbrbrbrIf you would like to rent the 2017 Yukon XL Denali-please reach out through messaging and we will send you additional information.brbrbrbrInteraction with Guests:brbrWe love hosting and are happy to help make your trip to Hilton Head Island unforgettable. While you’ll have complete privacy, we’re easily reachable if you need anything—from restaurant recommendations to quick assistance during your stay.

4BR Coastal Elegance Chef’s Kitchen Steps to Beach

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$722.38

This beautiful Charleston style 3100 sq. foot home is situated on a palm tree lined paving stone cul-de-sac within the private gated beach community of Singleton by the Beach. This community is located mid-island next to Palmetto Dunes and across from Chaplin Park. brbrCheck-in Time: 4 PM brCheck-out Time: 10 AM brbrPlease note that during the peak season (Memorial Day to Labor Day), we cannot accommodate early check-in or late check-out. brbrThe renter booking must be 25 years of age or older. If under 25, guests must be accompanied by a parent/legal guardian during the entire duration of the reservation.brbr **Max of 13 adults/children (2-12)**brThere is 1 mini crib and 2 pack’n plays for 3 additional infants. Inquire about additional guest(s) for an additional pro-rated fee per person, per night.brbr+ 4 Bedrooms (2 Kings, 4 Queens, 1 Twin, 1 Mini Crib) br+ 4 Full En-suite Bathroomsbr+ 10 minute walk/ 4 minute bike ride to beach br+ Free private community shuttle to and from beach 9-5pm (Memorial-Labor Day)br+ Free Wifibr+ Cable and Apple TVbr+ Two Accessible Balconies br+ Updated High End Finishesbr+ Private, Fully Fenced in backyard with covered Pool br+ Pool Heating is available for an extra minimum charge of $200 for 3 nights, then $50/night each additional night. Heating is only available when ambient outside temperature does not drop below 65 degrees Fahrenheit. To the best of our ability the pool will maintain a temperature of 88 degrees Fahrenheit when heated.brbrWHAT'S PROVIDED:br+ Contactless self check-inbr+ Free WiFibr+ 2 Pack 'N Playsbr+ 1 Highchairbr+ 1 Child bedrail for daybedbr+ Bed linensbr+ Towels (2 bath towels, hand towels, wash cloths) for every guestbr+ Starter set of shampoo, hair conditioner, body wash and soap in every bathroom br+ 2 Toilet paper rolls per bathroombr+ Tissuesbr+ Hairdryersbr+ Laundry detergentbr+ Iron and Ironing Board br+ Dishwasher soap, pods, sponge and 2 kitchen towelsbr+ Starter supply of trash bagsbr+ 1 Paper towel rollbr+ Fully equipped kitchenbr+ Nespresso Breville, standard drip coffee pot, Keurig (coffee pods not provided)br+ Toaster, blender, powered hand mixerbr+ Beach towelsbr+ Beach chairsbr+ Beach umbrellabr+ Beach wagonbr+ Beach (sand) toysbr+ Radio Flyer double seater wagonbr+ Double side by side fold up umbrella strollerbr+ Ping pong table and accessoriesbr+ Shuffleboard table br+ Second smaller sized fridge in garage br+ Outdoor Jumbo Connect 4- Poolsidebr+ Giant Jengabr+ Grillbr+ Outdoor Firepitbr+ High speed wireless internetbr+ Cable/Apple TVbr+ Smart TV'sbr+ Water filter in refrigerator is changed every 6 months br+ Fire Extinguisher brbrPlease note sometimes guests may purchase beach/ pool items and leave them in the garage for the next guests to use and enjoy. We are not responsible for the condition of any items not listed above.brbrATTRACTIONS:brColigny Beach ParkbrHarbour Town LighthousebrSea Pines Forest PreservebrShelter Cove Harbour & MarinabrPinckney Island National Wildlife RefugebrCoastal Discovery MuseumbrLawton StablesbrArts Center of Coastal CarolinabrDolphin and Nature ToursbrDriessen Beach ParkbrColigny ParkbrbrGOLF COURSES:brPalmetto Dunes Oceanfront Resort- Robert Trent Jones CoursebrPalmetto Dunes Oceanfront Resort- Arthur Hills CoursebrPalmetto Dunes Oceanfront Resort- George Fazio CoursebrHarbour Town Golf Links at Sea Pines ResortbrHeron Point by Pete Dye at Sea Pines ResortbrAtlantic Dunes by Davis Love III at Sea Pines ResortbrHilton Head National Golf Course brPort Royal Golf & Racquet Club- Barony CoursebrPort Royal Golf & Racquet Club- Planter's Row CoursebrPort Royal Golf & Racquet Club- Robber's Row CoursebrbrUpon entering this beautiful home, walk upstairs to the main floor and you will be welcomed by a spacious, coastal inspired design living room with plenty of seating along with a 50” flat screen TV. Off the living room via 3 sets of sliding doors is a private balcony where you can enjoy your coffee, book, or evening cocktails while enjoying the cool beach breeze and swaying palm trees. In the entertainment center in the living room are board games, puzzles, and books for your enjoyment. The living room flows into a fully stocked kitchen with full- sized appliances including a beverage refrigerator to prepare any meal. Note: additional wine refrigerator is out of order. There is a laundry room off the kitchen that is stocked with cleaning supplies, more cooking utensils, 2 folding chairs, 4 TV dinner tables, a cooler, step ladder, iron, ironing board, high chair, 2 baby pressure gates, broom/dust pan, and Dyson Animal cordless vacuum. There is a king suite on the main level with a bathroom also accessible from the hallway. Head upstairs for 3 additional bedrooms. The front king master suite with private balcony includes an ensuite double sink master bathroom retreat with a jetted jacuzzi tub and separate walk-in shower. This bedroom also includes a mini crib. The middle room has 2 queen beds along with a full bath and walk-in shower. The rear bedroom has 2 queen beds and a twin day bed along with another large ensuite double sink bathroom. There are 2 additional Pack ‘n Plays in the home. brbrThe private fenced in yard is a great entertaining area with an inviting covered pool which can be used even when it rains! A smart TV is mounted on a poolside wall, and can be watched when sitting anywhere in the backyard. The patio includes a lounge seating area, turfed area for games, propane gas BBQ/grill, bar area with sink, and Adirondack chairs surrounding a propane gas fire pit.brbrFrom the backyard you can head upstairs via the covered staircase into the kitchen of the home or enter the garage. The garage is on the same level as the pool, which has been turned into an entertainment room including a full size ping pong table, Jumbo Connect 4, Jumbo Jenga and Cornhole!brbrAlso, located in the garage are beach chairs, beach toys, pool toys, beach umbrellas, a double stroller, Radio Flyer wagon that seats 2 children, and beach cart. All are for guests to use during their stay. This home also includes beach towels during your stay. brThe driveway provides parking for 3-4 cars depending on size. Please no parking inside the garage. There is NO STREET PARKING allowed in the Singleton by the Beach community. brbrSingleton beach via a private access exclusive for this community is a comfortable walk (about 10 minutes) or a quick 4 minute bike ride from the house. There is a complimentary golf cart beach shuttle service exclusive to this community. It runs Memorial Day to Labor Day (Sunday through Friday 9am-5pm, weather permitting). The driver is in the community waiting on your call. He will pick you up at the house and take you back and forth to the beach as often as you like. There is only bike parking (no car parking allowed), at Singleton beach where the beach shuttle drops you off. If you prefer to drive, there is a public beach parking lot for Burke's beach, which is a 2 minute drive from the house.brbrThere is one exterior camera to monitor the exterior of our home. This is placed on the front right side of the house near the front door. The camera monitors the outside of the house at the front door, driveway, and street. Any attempt at disabling, redirecting or obscuring the camera is prohibited.brbrOverview of The Singleton Beach Community:brbrSingleton Beach Community is located centrally and is easy to get on and off the Island where the traffic of Hilton Head is not overwhelming. We love the nearby Chaplin Community Park (2 minute walk from the house) that has free tennis courts, a playground, basketball courts, soccer fields, covered picnic area, biking/walking trails and public restrooms. This home is also minutes away to multiple beautiful golf courses located on Hilton Head Island. brhttps://www.hiltonheadislandsc.gov/parks/Chaplin/brbrGrocery stores (close to Kroger, Publix, Harris Teeter, and Fresh Market), gas stations, and more shopping at Shelter Cove is a short 3 minute drive away. Located mid-island between Palmetto Dunes and the Marriott Surfwatch Resort, there is no shortage of things to do in this area. Whether you choose to make the scenic walk to Singleton Beach (approx. 700 yards away) or take the free beach shuttle, you will surely be pleased by the beautiful white sand beaches and relatively small crowds all year round. When it’s time to take a break from the sun, be sure to stop by “Coco’s on the Beach” restaurant for a refreshing frozen drink or quick bite to eat. Shelter Cove Towne Center located just 1.5 miles away offers a variety of restaurants such as Poseidon, with rooftop bar as well as Kilwins ice cream to go along with some of the finest waterfront shopping available. brbrThe town hosts a number of events and festivals throughout the year, including a firework display every Tuesday night during the summer that is best viewed from the Shelter Cove Community Park directly behind Shelter Cove Towne Center.brbrWe hope you create long lasting memories at our home as this was the purpose of this home for our family.brRelax, Unwind and Breathe in that salt air!brbrA few final reminders:brNo Smoking of any kind. No Pets. Due to severe allergies and health safety, there are NO animals at all allowed in this home. Please enjoy yourself and respect our home. Do not take furniture out of the villa or move it to another room or floor. Please do not re-arrange outdoor furniture. No trailers, kayaks, or canoes are allowed on the property. Bikes must be secured at bike racks by the beach. Bikes must also be kept off the grass when at the home so the landscapers can cut the grass. Please inquire about bike rental opportunities.brbrPlease acknowledge that we may leave consumables such as condiments, snacks, and spices. These are free and please indulge yourself as you desire. Ultimately, it is up to the Guests’ discretion and inspection to consume these items if they wish. The Owners do not take any responsibility or liability for the consumables or for any allergies that a Guest may have.

40 Crabline Court: Walk to beach, Seasonal Beach Shuttle, & Private Pool

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$516.22

OUR FOUR HOMES HAVE MONTHLY RATES FOR WINTER, DO INQUIRE.brLocated on quiet Baynard Park Road, across from the Heritage PGA 13th and 14th holes.brGreat location for those that enjoy nature and watching a lovely variety of birds that often visit our lawn.brThis is a beautifully renovated and comfortably furnished, 3000 plus square foot home. The Italian tiled Great Room has a wall of glass with a clear view over the large lawn, down to the lagoon & egret island. It enables anyone in the kitchen area to be part of the group. The Weber gas grill is located just outside on the patio, close to the kitchen. The dining area inside seats 8, plus 4 bar stools around the counter. On the patio, there are two dining areas. The four generously sized bedrooms, are located to offer privacy for each, and each enjoy their own bathroom.brThis home is designed to provide comfortable and easy vacation living with the several delightful outdoor sitting areas, two are fenced with gates. Sit on the terrace overlooking a lagoon and Egret Island, where in spring and early summer nesting egrets cover this island. Swim or relax around the private courtyard pool. Two bedrooms open into this area and there is a special area for doggy convenience. The entryway courtyard with small garden has table & chairs for quiet times and shade.brThe Master Bedroom has 12 feet of French doors leading into the courtyard pool area. A second bedroom also opens up into this area. brGreat Room consists of:brAn open kitchen area, with granite countertops and counter seating for 4.brDining room table seats 8. brLiving area has a sofa and arm chairs grouping surrounding the large flat screen TV.brWifi.brGames table for cards, backgammon or chess.br4 bedrooms, each with flat screen TVs & each bedroom has their own sitting area outside of their glass doors.brIn 3 bedrooms there are king sized beds, br4th bedroom has a 1 full bed, 1 twin bed and a twin sized sofa bed with comfortable foam mattress.br3 bedrooms have bathrooms with showers en suite.br4th bedroom has bathroom immediately across the hall with tub/shower.br2 bedrooms overlook the lagoon, the other two have direct access to the pool.brPool can be heated in spring and fall, a half bathroom is adjacent to pool area with a supply of towels for pool use. There are chaise lounges and poolside chairs to relax in & soak up the sun, when not swimming. For doggy guests the enclosed courtyard offers them safety and freedom making it very convenient for their owners and allowing them to share time together.brLaundry room includes front load washer, top load washer and two dryers.brWeber gas barbecue grill outside of kitchen overlooking the lagoon, two outside dining tables. brWhile we are pet friendly, dogs only, there is no limit to size, however dogs must be one year or older. We do charge a pet fee of $225.00 for each dog, limit of 2 dogs unless by special agreement with us, the owners.brOur guests satisfaction is of upmost importance to us.brWe manage our homes personally, working directly with our guests to ensure their stay in our home is a comfortable and enjoyable one. We are available to them twenty for hours a day.brRegarding our other THREE HOMES listed on HomeAway. Their VRBO numbers are 239212, 7263910 and 3523347 these are all on Live Oak Road.brFor those who like to bike ride, we have arrangements with Riding Tigers Bike Rentals to obtain discounted pricing on bike rentals for our guests. Simply call them and ask for the discount. They offer free delivery and pickup also.brTheir number will be shown on our Welcome Letter we send to our guests.brWe do require our Lease Agreement, found on the rental booking page, to be completed and returned to us. In turn we furnish each renter with a copy. We send informative Welcome Letters and closer to arrival a descriptive letter regarding the house, and our pet policy while your furry companion is visiting with you. Also a Sea Pines Community Letter.brbrBusiness License No. 13469

Walk to RBC Heritage course. Reduced winter Rates. Pet friendly, pool.

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$1735.25

Want a preview what heaven is like Stay at 1 Capri. This spectacular, designer palace just 60 seconds from the beach feels like the hug you didn’t know you needed, it’s the massage you never want to end. You’ll leave relaxed, refreshed and full of unforgettable memories with your favorite humans. brbrEveryone in your group will sleep like a baby in one of the 7 bedrooms and there’s no excuse for anyone not to be cleaned up for dinner with 6.5 bathrooms. brbrNot a beach bum No problem! Take a dip or lounge by the new pool, hot tub, work on your ping pong game or check out your favorite show on one of our 8 TVs. brbrYou’ll feel ready for your own Food Network show cooking in the state of the art kitchen, which has all of the bells and whistles, including granite countertops, an island fit for a queen, a 10 seater table, a 6 person breakfast nook and 5 counter bar seats. Not into cooking No problem--stroll or bike up to Coligny Plaza for many delectable options.brbrYou thought it couldn’t get any better You’re wrong! We have an elevator should you need it, well stocked sand castle making tools and numerous other beach tool delights, beach chairs galore and a screened in porch, which is the best spot to devour James Patterson’s latest whodunit. brbrWhat are you waiting for Pack up that sunscreen and your comfiest swimsuit. We look forward to welcoming you soon!brbrOur property is compliant with all Town of Hilton Head Short Term Rental Certification and Licensing Ordinances. Our Short Term Rental Permit is # 072006.

Beach Home-Elegant Contemporary Design...Spacious Deck Pool Spa Area...Elevator

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$1349.15

Summary:brbrWhere Luxury, value and comfort meet. One Sweet Stay proudly presents, this #1 rated, 5 star reviewed luxury 7 bedroom/4-bath Hilton Head beach house for large groups. This home features a private heated saltwater pool, hot tub, all-level elevator, and game room (Ping Pong, XBOX, PS4). From this gated Resort Community, it's just a 7-min walk to Folly Field Beach. Enjoy high-end amenities, a gourmet kitchen, & EV charger. We provide beach gear, cribs, and high chairs for a perfect family getaway.brbrbrbrThe Space:brbrThe day before arrival you will receive a 4 digit access code for the property as well as other security and access information. This 4 floor home DOES have an elevator however it should not be relied on for people with mobility issues and unable to navigate stairs. If the detailed instructions for its operation are not followed, the security and safety system will be tripped and it takes many days to get the service company here to reset it (it can not be put back online during your stay if it goes down due to operation errors). Children are not allowed in the elevators unless with an adult. No refunds will be provided for equipment or amenity unavailability or failure if beyond our control.brbrbrbrThe Neighborhood:brbrLocated in the Resort Inspired community of Sandcastles by the Sea a few hundred yards from Folly Field Beach.brbrbrbrGetting Around:brbrRestaurants, bars, Beach all within a 10 minute walk. NO STREET PARKING ALLOWED. MAX OF 5 CARS (standard and compact sized) WILL FIT IN THE GARAGE / DRIVEWAY. Oversized trucks are not recommended, they will consume most of your parking area.brbrbrbrOther Things to Note:brbr****Please note any cancellations where Cobble and Key DBA One Sweet Stay is the merchant of record (VRBO and Direct Bookings) will be subject to card processing and platform fees not being returned. Otherwise, refunds will be made in accordance with the policy at the time of booking****

Saltwater Pool, Hot Tub, Luxury, Big Groups

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$334.86

Welcome to The Green Turtle, your ideal retreat in the Palmetto Dunes Resort on Hilton Head Island! brbrThis charming, townhome-style end unit in Turnberry Village offers a perfect blend of comfort and coastal charm, just minutes from the beach. Situated within the picturesque Palmetto Dunes Resort, The Green Turtle is a short walk from the beach and the community saltwater pool. Enjoy easy access to nearby grocery stores, shopping, and dining options. brbrThe villa is tastefully designed with a soothing coastal theme, enhanced by abundant natural light. Guests enter through the front door and ascend a half-flight of stairs to reach the dining room, which connects to the kitchen, living room, and back deck. The first floor has a king bedroom and bathroom (also serves as a guest bathroom), while the second floor features a den that opens to the living area below with two twin beds which leads to the guest bedroom with two full beds and an additional bathroom. The renovated kitchen boasts quartz countertops, stainless steel appliances, and a tiled backsplash. brbrRelax on the partially covered back deck, which offers views of the 8th green of the George Fazio golf course. Enjoy alfresco dining with a table that seats four and a gas BBQ grill. Perfect for catching the Sunset over the golf course! brbrThis property offers 2 Complimentary Hours of Tennis and Pickleball at the Palmetto Dunes Tennis Center just a walk away!!!brbrPalmetto Dunes offers three golf courses, miles of sandy beaches, and complimentary Dunes Buggy transportation for easy access to Shelter Cove and other attractions.brbrProperty Highlights:brPet friendly! brEnd Unit with lots of sunshine! brDeck area to enjoy the serene views of the golf course and island nature brBeach towels to accommodate 7 guests brRoughly a mile to the beach - Short bike ride! brComplimentary On Demand Shuttle - Palmetto Dunes Beach Buggy- SeasonalbrComplimentary WifibrKeyless EntrybrSquare Footage: 1473br2 Hours of Complimentary Tennis/Pickleball at Palmetto Dunes Tennis Center!brbrCommunity Features:brCommunity Saltwater Pool - opened seasonally from April to October brLarge Sundeck brShaded PavilionbrbrBedding: Sleeping Arrangements: (Sleeps 8)brSecond Floor:br- Bedroom 1: 2 Full Bedsbr- Loft: Two Twins brbrFirst Floor:br- Bedroom 2: King BedbrbrDistances brBeach - 1 mibrColigny - 5.7 mibrHarbor Town - 7.9 mi brShelter Cove - 2.7 mi brbrHH STR Permit #75754

255 Turnberry-Fazio Course Views, Dog Friendly, Free Tennis

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$609.46

Sleeps 8 | 3 Bedrooms | 2 BathroomsbrPet-Friendly! (Dogs Only) | 5-minute walk to the beachbrSingle Level Home | Beach Towels Providedbrbr7 Jessamine is a single-level home nestled in the heart of Sea Pines on Hilton Head Island. This 3-bedroom, 2-bathroom home comfortably sleeps 8 and is perfect for your next family vacation to Hilton Head. The home is at the end of the street, providing extra privacy during your stay while still within walking and biking distance of all the Sea Pines amenities, oceanfront restaurants, and beaches.brbrWhen you stay at 7 Jessamine, you will immediately be immersed in the beauty and relaxation of the Lowcountry. The open floor-plan living space makes entertaining a breeze. This is the perfect space to gather around for a movie at night on the Blu-Ray DVD player, play a game on the Xbox 360, or watch your favorite football game during the fall on cable. The gourmet kitchen is fully equipped with everything you will need to prepare meals during your stay from luxury stainless steel appliances, granite countertops, coffee brewers, pots and pans, utensils, and more! With 2 seating areas, 2 indoor dining spaces, and 2 bedroom wings the home provides everyone with their own space while still allowing you to gather.brbrJust off the dining room, the primary suite features a king-sized bed, TV, and a spacious ensuite with a tiled walk-in shower. This bedroom provides relaxation and a window to nature with access to the patio where you can enjoy your morning coffee. On the other side of the home, you will find the laundry room and the 2 other bedrooms which share a spacious hall bathroom with a tiled walk-in shower. Bedroom 2 is perfect for kids, teens, or even adults with 2 bunk beds! Bedroom 3 has a queen-sized bed and a beautiful view of the backyard through the French doors.brbrIt is no surprise that guests will spend most of their time outside when visiting Hilton Head Island, especially when you have an outdoor space like 7 Jessamine does. Whether you want to enjoy your morning coffee out back, cook up a meal on the gas grill, open the French doors for dinner, and let in the ocean breeze, you will truly experience coastal luxury here. Plus, this home is dog-friendly and perfect for your four-legged friend! With miles of walking and beach paths, a spacious yard and so many pet-friendly restaurants on the Island, your dog will feel right at home! brbr After a long day of golfing, swimming, or relaxing on the beach you can throw your sandy clothes in the wash and don't have to worry about tracking any sand back home with you! brbrDon't forget that 2 bikes are included with most stays which makes it easy to explore all that Sea Pines has to offer! Book your next Hilton Head Island vacation at 7 Jessamine today so you can be close to the ocean and make memories that will last a lifetime. You will want to return year after year!brbrSave even more when you book 7 Jessamine and receive $300 in complimentary daily activities! Your amenities include 2 backpack beach chairs, an umbrella, 2 adult bikes, and admission to dolphin tours. When you're not soaking up the sun at the beach, enjoy daily rounds of golf at 6 local courses with a golf cart included and mini golf for family fun!brbr*Total number of vehicles allowed is 5, with 4 in the driveway and 1 in the carport.br*This property is in the gated community of Sea Pines and a car pass is required for every vehicle. 2 car passes are included with your reservation. Additional car passes can be requested AFTER booking for $15 each + taxes. The number of car passes that can be issued for the property is based on how many vehicles are allowed. br*2 dogs allowed. $250 non-refundable pet fee per pet.br*3-night minimum stay required. br*4-night minimum stay required for RBC Heritage April 16-19, 2026.br*Free daily activities are not available to monthly renters, long-term renters, or stays beyond 27 nights. br*South Beach Marina Pool is closed on September 5th for the rest of the 2025 season.br*Please note that once the pool is reopened, daily and weekly pool passes will be available for purchase on-site at the South Beach pool during normal pool hours. br*Short Term Rental Permit #23777

Beautiful single-level home within walking distance of Sea Pines beach and ocean!

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$1150.26

Welcome to 1 Cedar Waxwing, a quintessential, luxurious Hilton Head vacation home. This 5-bedroom, 5.5-bathroom, 4th row home is located on a corner lot in Sea Pines, offering guests premier accommodations with ample space and privacy. brbrThe elevated main level features an open-concept floor plan. The living area is comfortably furnished with a couch, loveseat, two oversized chairs and a Smart TV. Just off the living area you'll find a separate den with a Smart TV for added enjoyment. brbrThe main living area is open to the gourmet kitchen and dining area. The dining area seats 8 with additional seating for 6 at the kitchen island. The kitchen features stainless steel appliances, ample counter and cabinet space, as well as a bar area with a wine fridge and ice maker just beyond. brbrThree of the guest bedrooms are located on the main level, including the primary suite. This bedroom features a king bed, a Smart TV, and a private bathroom with dual sinks and a spacious walk-in shower. The next bedroom features a king bed, a Smart TV, and a private bathroom with a tub/shower combination. The final bedroom on this level has a king bed, Smart TV and private bath with a walk-in shower. brbrThe remaining two bedrooms are located upstairs. One bedroom has a queen and XL twin bunk beds, while the other has a full and XL twin bunks, making the rooms perfect spaces for kids or adults! Both rooms have Smart TVs and private bathrooms. brbrThe spectacular exterior will have you rebooking this home year after year! There is an elevated covered patio overlooking the pool area with a Smart TV and comfortable furniture. The main deck surrounds the pool and spa*, with additional seating, a gas grill, and an outdoor shower room for rinsing off after a day at the beach. Guests also have access to a ping pong table!brbr*Pool and spa can be heated for additional fees March - May and September - November, weather permitting. Pool and/or spa heat must be arranged at least 2 weeks before arrival. brbrVehicle Policy: Sea Pines requires each vehicle to have a gate/car pass. Car passes are $17.00 per car per week. Parking for 4 vehicles max. brbr**Fireplace is not for guest use.**brbrCedar Waxwing 1 is located in Sea Pines, Hilton Head Island's original and largest planned resort. While it is currently the home of the annual Heritage Golf Tournament, it is the abounding natural beauty of Hilton Head Island that beckons one to return again and again. Five miles of white sandy beach offer swimming, sailing, parasailing, kayaking, and fishing. For the land lovers, there are 14 miles of bike paths, 3 golf courses, tennis, and a broad range of shops and restaurants that will please every vacationer.brbr*Please contact Sunset Rentals to purchase additional car passes* brbrFor specials, promotions, deals and additional availability please contact our local Hilton Head Island sales agents at Sunset Rentals.brbrCheck-in instructions will be sent via email at least 10 days prior to check-in once the Rental Agreement is signed. If your stay is within 9 days, or lesser, from the time of booking, the instructions will be sent via email as soon as the Rental Agreement is signed.brShort Term Rental Permit # 025610

Sunset Rentals | Cedar Waxwing 1

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$1646.61

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.brbrThis charming Sea Pines home is 4th row from the beach and features 5 bedrooms along with 5 bathrooms and 2 half bathrooms to host 14 guests very comfortably.brbrThe first floor features a very open floor plan that offers easy access between the multiple living spaces, kitchen and wet bar, and dining room. Guests can enjoy plenty of comfortable seating in the tastefully decorated main living room; this room is spacious and has high ceilings that create an open, inviting space that everyone will love relaxing in. There is a flatscreen TV for your entertainment, as well as plenty of books and games that make perfect for peaceful rainy days. There is another full sitting area right around the bend, complete with a flatscreen TV, making this the perfect vacation home for families or groups! Both spaces have direct access to the wrap-around porch and private pool! The kitchen is massive and is sure to make guests’ culinary experiences a breeze. Enjoy top-of-the-line stainless steel appliances along with plenty of counterspace that allows for multiple people to cook simultaneously. There is plenty of seating at both dining tables, as well as additional seating at the kitchen bar.brbrThe master bedroom sits on the first floor and features a king-sized bed, flatscreen TV, window-side seating, and direct access to the wrap-around porch and pool. The master bathroom is very spacious and features 2 vanities, a spa tub, a walk-in shower, and a large walk-in closet. Upstairs, you are met with another sitting room before uncovering the rest of the bedrooms. Bedroom 2 serves as a suite and features 2 queen-sized beds, a flatscreen TV, window seating overlooking the pool, and a large, private bathroom that has a double vanity, a spa tub, and a walk-in shower. Bedroom 3 features two twin beds over full-sized beds and a private bathroom with a shower/tub combination. Bedroom 4 features a king-sized bed along with a flatscreen TV, walk-in closet, and private bathroom with a walk-in shower. Bedroom 5 serves as a second suite and features a king-sized bed, a flatscreen TV, tons of closet space, and a huge private bathroom complete with a spa tub and walk-in shower.brbrOutside, fun in the sun awaits! The private pool and spa deck are lusciously surrounded by nature to offer the most privacy. Guests can enjoy relaxing poolside in the loungers or perhaps a game of basketball in the pool! There is a gas grill and plenty of space at the outdoor dining tables for everyone. The wrap-around porch has plenty of rocking chairs and makes for the perfect place to sip your morning coffee or have a cocktail on a moonlit night. The beach path will have sand in between your toes in no time—Royal Tern is perfect for your next vacation!brbrKey Features:br• Proximity to the beach: 4th row br• The pool and spa can be heated for an additional charge, give us a call for heating rates and to make arrangements. Pool and spa heat must be scheduled at 14 days prior to arrival. Additional fees apply for last minute requests prior to arrival or after arriving at the property. If the weather drops below 60 degrees, the pool may not be capable of being heated and or reaching optimal temperature. br• Outdoor shower br• Pets are not allowedbr• Sea Pines Resort AmenitiesbrbrRent price includes: Rental Rate, Hospitality Program, Beach Gear Credit, Booking Processing Fees, and Departure Clean. Your Luxury Concierge is included with no additional cost.brbrAccount #/STR Permit #070318

Pristine 4th row beach home with gorgeous updates and private pool & spa!

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$245.19

Completely renovated and newly decorated two bedroom two and a half bathroom townhome ready for your stay. Tennismaster condominiums are within the gated community of Shipyard, a private residential and resort community. The complex is close to the Atlantic Ocean, and the Van der Meer Tennis Center. Guests staying at Tennismaster 204 can easily walk to dining and entertainment venues offered by the Sonesta Resort. King in master bedroom, queen in second bedroom, plus a sleeper sofa in the living room. The Shipyard Golf Course has a unique combination of 9, 18, or 27 holes available for play. Just beyond the Shipyard gate on Pope Avenue, vacationers can find a wide selection of restaurants, shopping venues, and entertainment for all ages at Coligny Plaza in North Forest Beach as well as the new Low Country Celebration Park.

Gorgeous 2 BR 2.5 BA Shipyard Townhouse

Hilton Head Island, South Carolina, United States

Bed

Bath

6

Sleeps

$328.18

Escape to this spacious 2-bedroom villa in Sea Pines, perfect for up to 8 guests! Featuring a twin suite off the living room with a shared ensuite, plus a luxurious master suite upstairs with a state-of-the-art shower and granite countertops. Two pull-out couches—one on each floor—offer extra sleeping space. Enjoy comfort and convenience in a prime Hilton Head location, just minutes from the beach, golf, and dining!brbrWelcome to Your Ideal Island Getaway!brThis thoughtfully designed 2-bedroom, 2-bathroom villa offers a spacious and flexible layout with tasteful upgrades throughout—perfect for families, couples, or small groups seeking comfort and relaxation.brbrStep inside to discover two beautifully appointed bedrooms, starting with a twin suite located on the main floor. This room features an en-suite bathroom with elegant stone countertops and modern fixtures. The bathroom is cleverly configured to also serve the main living area, offering both privacy and convenience.brbrThe fully equipped kitchen is stocked with all the essentials—from appliances to cookware—so you can easily prepare family meals or your morning coffee. A full-sized washer and dryer are also tucked into this space for added ease during longer stays. The dining area comfortably seats six and flows seamlessly into the open-concept living room, where you’ll find a cozy sleeper sofa and direct access to a private back patio. Additional seating is available at the breakfast bar, perfect for casual meals or entertaining.brbrUpstairs, the spacious master suite offers a peaceful retreat with a plush king-sized bed, a luxurious double vanity, and a walk-in tiled shower for a spa-like experience. Just outside the master bedroom, a versatile loft area doubles as a home office or game room and features a game table along with a second sleeper sofa—great for kids, guests, or extra lounging space.brbr Highlights:br2 Bedrooms | 2 Bathrooms | Sleeps 8brbr- Master bedroom upstairs with king bed, double vanity, and walk-in showerbr- Twin bedroom on main floor with shared en-suite accessbr- Modern bathrooms with stone countertops and elegant finishesbr- Sleeper sofa in living room and additional sleeper in upstairs loftbr- Loft space perfect for games, work, or winding downbr- Open-concept main living area with comfortable furnishingsbr- Fully equipped kitchen and dining area for meals at homebrbr*The house is located in Sea Pines gated community that requires a car pass. Guests are required to purchase a weekly rental, car pass at the main gate for $20 in CASH only.

2896 - Private 2 BD Retreat + Pool + Lagoon View

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$338.18

Escape to this spacious 2-bedroom villa in Sea Pines, perfect for up to 8 guests! Featuring a twin suite off the living room with a shared ensuite, plus a luxurious master suite upstairs with a state-of-the-art shower and granite countertops. Two pull-out couches—one on each floor—offer extra sleeping space. Enjoy comfort and convenience in a prime Hilton Head location, just minutes from the beach, golf, and dining!brbrWelcome to Your Ideal Island Getaway!brThis thoughtfully designed 2-bedroom, 2-bathroom villa offers a spacious and flexible layout with tasteful upgrades throughout—perfect for families, couples, or small groups seeking comfort and relaxation.brbrStep inside to discover two beautifully appointed bedrooms, starting with a twin suite located on the main floor. This room features an en-suite bathroom with elegant stone countertops and modern fixtures. The bathroom is cleverly configured to also serve the main living area, offering both privacy and convenience.brbrThe fully equipped kitchen is stocked with all the essentials—from appliances to cookware—so you can easily prepare family meals or your morning coffee. A full-sized washer and dryer are also tucked into this space for added ease during longer stays. The dining area comfortably seats six and flows seamlessly into the open-concept living room, where you’ll find a cozy sleeper sofa and direct access to a private back patio. Additional seating is available at the breakfast bar, perfect for casual meals or entertaining.brbrUpstairs, the spacious master suite offers a peaceful retreat with a plush king-sized bed, a luxurious double vanity, and a walk-in tiled shower for a spa-like experience. Just outside the master bedroom, a versatile loft area doubles as a home office or game room and features a game table along with a second sleeper sofa—great for kids, guests, or extra lounging space.brbr Highlights:br2 Bedrooms | 2 Bathrooms | Sleeps 8brbr- Master bedroom upstairs with king bed, double vanity, and walk-in showerbr- Twin bedroom on main floor with shared en-suite accessbr- Modern bathrooms with stone countertops and elegant finishesbr- Sleeper sofa in living room and additional sleeper in upstairs loftbr- Loft space perfect for games, work, or winding downbr- Open-concept main living area with comfortable furnishingsbr- Fully equipped kitchen and dining area for meals at homebrbr*The house is located in Sea Pines gated community that requires a car pass. Guests are required to purchase a weekly rental, car pass at the main gate for $20 in CASH only.

2897 - Poolside Lagoon Views, Hot Tub - Sleeps 8

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$1061.83

Welcome to Osprey Overlook – Pool, Spa & Marsh-Front Retreat in Sea Pinesbr22 Audubon Pond Drive | Sea PinesbrbrEscape to Osprey Overlook, a 3-bedroom, 3-bathroom Sea Pines retreat with a large private pool, standalone spa, and an expansive backyard that opens to the tranquil tidal marsh. This family-friendly home sleeps up to 12 guests and sits approximately 0.6 miles from the nearest beach access, making it an ideal base for beach days, bike rides, and evenings under the Lowcountry sky.brbr ️ Bedroom Configuration – Sleeps 12br Primary Suite – King bed, Smart TV, ensuite 5-piece bathroom with soaking tub, walk-in shower, and dual vanitiesbr Bunk Room – 2 twin-over-queen bunk beds, Smart TV, ensuite bathroom with standing showerbr Bedroom 3 – King bed, Smart TV, shares Jack-and-Jill bathroom with dual sinks and tub/shower combobr ️ Den – Queen sleeper sofa, Smart TV, shares Jack-and-Jill bathroom with dual sinks and tub/shower combo, plus desk area for remote workbrbr Interior Highlightsbr ️ Main Living Area – Comfortable coastal-inspired seating with Smart TV and easy flow to kitchen and pool areabr ‍ Chef's Kitchen – Quartz countertops, gas range, wine fridge, and island seating for 4, perfect for group meals and entertainingbr ️ Dining Area – Table seating for family dinners, game nights, or additional workspacebr Flexible Den Space – Extra lounge and sleeping area ideal for kids, teens, or an additional couple, with a dedicated desk setup for work-from-vacation daysbrbr Outdoor Amenitiesbr ‍♂️ Large Private Pool – Spacious pool for all-day fun; propane pool heat available for an additional fee (approximately $600–$1,500 per week depending on season, prorated for shorter or longer stays)br Standalone Spa – Separate spa heated complimentary for guests year-round, ideal for relaxing soaks after beach or bike daysbr Massive Marsh-Front Backyard – Expansive yard backing up to the serene tidal marsh, offering peaceful views and a true Lowcountry backdropbr Outdoor Living – Sun loungers for poolside relaxation, outdoor dining table for al fresco meals, and an outdoor lounging area perfect for morning coffee or evening cocktailsbr Propane Grill – Full-size propane grill provided, with propane included and the grill cleaned and maintained before every check-in for a hassle-free cookout experiencebrbr Bonus Beachside HHI Amenitiesbr Guest Support – Personalized, local assistance from the Beachside HHI teambr Luxury Essentials – Full-size body wash, shampoo, and conditioner in every full bathroombr ️ Beach Gear – Turkish beach towels, soft-sided cooler, and a complimentary umbrellabr☕ Coffee Perks – Keurig and drip coffee makers with a starter supply of K-Cups, creamers, and sweetenersbr Household Conveniences – Starter supply of dish soap, paper products, trash bags, and a bulk supply of dishwasher pods and laundry podsbr ‍♀️ Hair Dryers – Available in every full bathroombr Smart Home Features – Keyless entry, high-speed Wi‑Fi, and Smart TVsbr Charging Connections – Bedside USB-C and USB-A power bricks in bedrooms (where equipped)br Extras Available – Bikes, beach gear, and baby equipment available to rent through trusted local partnersbrbr Explore Sea PinesbrSea Pines is a 5,000-acre private, gated community offering a mix of relaxation and adventure:brbr ️ Nearest Beach Access - .6 miles - about a 15 minute walk or a 4-5 minute bike ride!br Harbour Town – Lighthouse, boutique shops & waterfront dining (2.8 miles)br South Beach Marina – Home to the Salty Dog Café (1.4 miles)br Lawton Stables – Horseback riding & scenic trails (2.9 miles)br⛳ Sea Pines Beach Club – Dining & beach access (2 miles)br Golf & Tennis – Championship golf & world-class pickleball facilitiesbrbr Getting AroundbrSea Pines offers 5 miles of beach, miles of shaded bike paths, golf, tennis, pickleball, and beautiful marsh and harbor views. Biking is one of the best ways to explore Sea Pines, with multi-use paths connecting the beach, Harbour Town, South Beach, and Lawton Stables. During peak seasons, the Sea Pines trolley offers an additional, convenient option to reach key destinations without moving the car.brbr Why You'll Love Osprey Overlookbr Large private pool plus standalone spabr Massive backyard backing up to the tidal marsh for serene Lowcountry viewsbr ‍♂️ Short walk or quick bike ride (approx. 0.6 miles) to beach accessbr ‍ ‍ ‍ Bunk room + den sleeper layout ideal for families and multi-generational groupsbr Chef's kitchen with gas range, wine fridge, and island seating for 4br Dedicated desk area in the den, perfect for remote workbr Propane grill with propane provided and grill cleaned prior to every check-inbrbr Important Informationbr Check-In & Check-Out – 4 PM check-in / 10 AM check-outbr Gate Passes – 1 complimentary Sea Pines gate pass included; additional passes available at $20 per vehicle per weekbr Parking – Maximum of 6 cars allowed at the homebr Pool & Spa Heat – Pool heat available for an additional fee (approx. $600–$1,500 per week depending on season, prorated for length of stay); standalone spa heat included at no additional chargebr Non-Smoking – All Beachside HHI properties are strictly non-smokingbr Renter Age – Primary guest must be 25+ to bookbr Grill – Propane grill provided, propane included, and grill cleaned before every check-inbrbr Pet PolicybrWe welcome well-behaved dogs at this home! Pet fees apply as follows:brbr• $225 per pet, per staybrbrMore than three pets Just reach out—we review on a case-by-case basis.brbrEmotional support animals (ESAs) are not service animals and are subject to pet fees. Service animals are always welcome, and no fees apply—but we kindly ask you let us know in advance.brbr Book your stay at Osprey Overlook and experience a spacious Sea Pines retreat with a large private pool, complimentary heated spa, and sweeping marsh views in the heart of Hilton Head Island.

Sea Pines Marsh-Front Retreat w/ Pool, Spa & Near Beach ~ Pets ~ 22 Audubon Pond Drive

Hilton Head Island, South Carolina, United States

3

Bed

3

Bath

12

Sleeps

$1486.89

This gorgeous LowCountry home screams relaxation with its enormous front and back porches and lagoon views.brbrWhen you enter this home, you are greeted by a light and bright two-story entry that leads you through to the living room and straight back to another expansive porch. The living room has a large sectional centered around a decorative fireplace and a large screen tv, perfect for your cozy nights in. The doors from the living room lead you out to a huge, covered porch overlooking the pool and lagoon. Open to the living room is a large breakfast room that leads to the kitchen. The kitchen has stainless appliances, plenty of countertop and breakfast bar space and an abundance of room for people to work together in the kitchen. The dining room seats eight. Also on the main floor is the master bedroom. The master bedroom features a king bed, TV, private bath with double vanity, large shower, and deep soaker tub. Also from this bedroom are French doors that leads you to the large covered back porch with a living area.brbrThe second floor is where you will find the four additional bedrooms; each with a TV, private bathroom and access to one of the four expansive porches. The two bedrooms facing the front of the house have a queen bed. One of the bedrooms facing the back of the house has two bunk beds, each bunk has a double bed on bottom and twin bed on top. The fourth bedroom is the second master bedroom with a king bed and a private bath with large tub, walk in shower and a double vanity.brbrThe highlight of this house is the outdoor living. The lower-level back porch features and outdoor living area and a dining table seating six. A double staircase will lead you down to the lagoon shaped pool and grill area. Beyond the pool is the lagoon with a private dock, perfect for viewing wildlife or doing a little fishing. At the end of those long days on the beach this backyard is the perfect place to unwind.brbr*Pool heat available for additional fee. Pool heat requests must be made at least 2 weeks prior to arrival date to ensure the best service. Please note it can take up to 24 hours for the pool to heat.

5 Bed/5.5 Bath Home in Palmetto Dunes with Front and Back Porch

Hilton Head Island, South Carolina, United States

5

Bed

5

Bath

12

Sleeps

$368.51

Escape to this spacious 2-bedroom villa in Sea Pines, perfect for up to 8 guests! Featuring a twin suite off the living room with a shared ensuite, plus a luxurious master suite upstairs with a state-of-the-art shower and granite countertops. Two pull-out couches—one on each floor—offer extra sleeping space. Enjoy comfort and convenience in a prime Hilton Head location, just minutes from the beach, golf, and dining!brbrWelcome to Your Ideal Island Getaway!brThis thoughtfully designed 2-bedroom, 2-bathroom villa offers a spacious and flexible layout with tasteful upgrades throughout—perfect for families, couples, or small groups seeking comfort and relaxation.brbrStep inside to discover two beautifully appointed bedrooms, starting with a twin suite located on the main floor. This room features an en-suite bathroom with elegant stone countertops and modern fixtures. The bathroom is cleverly configured to also serve the main living area, offering both privacy and convenience.brbrThe fully equipped kitchen is stocked with all the essentials—from appliances to cookware—so you can easily prepare family meals or your morning coffee. A full-sized washer and dryer are also tucked into this space for added ease during longer stays. The dining area comfortably seats six and flows seamlessly into the open-concept living room, where you’ll find a cozy sleeper sofa and direct access to a private back patio. Additional seating is available at the breakfast bar, perfect for casual meals or entertaining.brbrUpstairs, the spacious master suite offers a peaceful retreat with a plush king-sized bed, a luxurious double vanity, and a walk-in tiled shower for a spa-like experience. Just outside the master bedroom, a versatile loft area doubles as a home office or game room and features a game table along with a second sleeper sofa—great for kids, guests, or extra lounging space.brbr Highlights:br2 Bedrooms | 2 Bathrooms | Sleeps 8brbr- Master bedroom upstairs with king bed, double vanity, and walk-in showerbr- Twin bedroom on main floor with shared en-suite accessbr- Modern bathrooms with stone countertops and elegant finishesbr- Sleeper sofa in living room and additional sleeper in upstairs loftbr- Loft space perfect for games, work, or winding downbr- Open-concept main living area with comfortable furnishingsbr- Fully equipped kitchen and dining area for meals at homebrbr*The house is located in Sea Pines gated community that requires a car pass. Guests are required to purchase a weekly rental, car pass at the main gate for $20 in CASH only.

2902 - Swallowtail Sleeps 8. Sea Pines Villa, Heated Pool

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$328.18

Escape to this spacious 2-bedroom villa in Sea Pines, perfect for up to 8 guests! Featuring a twin suite off the living room with a shared ensuite, plus a luxurious master suite upstairs with a state-of-the-art shower and granite countertops. Two pull-out couches—one on each floor—offer extra sleeping space. Enjoy comfort and convenience in a prime Hilton Head location, just minutes from the beach, golf, and dining!brbrWelcome to Your Ideal Island Getaway!brThis thoughtfully designed 2-bedroom, 2-bathroom villa offers a spacious and flexible layout with tasteful upgrades throughout—perfect for families, couples, or small groups seeking comfort and relaxation.brbrStep inside to discover two beautifully appointed bedrooms, starting with a twin suite located on the main floor. This room features an en-suite bathroom with elegant stone countertops and modern fixtures. The bathroom is cleverly configured to also serve the main living area, offering both privacy and convenience.brbrThe fully equipped kitchen is stocked with all the essentials—from appliances to cookware—so you can easily prepare family meals or your morning coffee. A full-sized washer and dryer are also tucked into this space for added ease during longer stays. The dining area comfortably seats six and flows seamlessly into the open-concept living room, where you’ll find a cozy sleeper sofa and direct access to a private back patio. Additional seating is available at the breakfast bar, perfect for casual meals or entertaining.brbrUpstairs, the spacious master suite offers a peaceful retreat with a plush king-sized bed, a luxurious double vanity, and a walk-in tiled shower for a spa-like experience. Just outside the master bedroom, a versatile loft area doubles as a home office or game room and features a game table along with a second sleeper sofa—great for kids, guests, or extra lounging space.brbr Highlights:br2 Bedrooms | 2 Bathrooms | Sleeps 8brbr- Master bedroom upstairs with king bed, double vanity, and walk-in showerbr- Twin bedroom on main floor with shared en-suite accessbr- Modern bathrooms with stone countertops and elegant finishesbr- Sleeper sofa in living room and additional sleeper in upstairs loftbr- Loft space perfect for games, work, or winding downbr- Open-concept main living area with comfortable furnishingsbr- Fully equipped kitchen and dining area for meals at homebrbr*The house is located in Sea Pines gated community that requires a car pass. Guests are required to purchase a weekly rental, car pass at the main gate for $20 in CASH only.

2905 - Scenic Villa | Pool | Sea Pines | Sleeps 8

Hilton Head Island, South Carolina, United States

Bed

Bath

Sleeps

$328.18

Escape to this spacious 2-bedroom villa in Sea Pines, perfect for up to 8 guests! Featuring a twin suite off the living room with a shared ensuite, plus a luxurious master suite upstairs with a state-of-the-art shower and granite countertops. Two pull-out couches—one on each floor—offer extra sleeping space. Enjoy comfort and convenience in a prime Hilton Head location, just minutes from the beach, golf, and dining!brbrWelcome to Your Ideal Island Getaway!brThis thoughtfully designed 2-bedroom, 2-bathroom villa offers a spacious and flexible layout with tasteful upgrades throughout—perfect for families, couples, or small groups seeking comfort and relaxation.brbrStep inside to discover two beautifully appointed bedrooms, starting with a twin suite located on the main floor. This room features an en-suite bathroom with elegant stone countertops and modern fixtures. The bathroom is cleverly configured to also serve the main living area, offering both privacy and convenience.brbrThe fully equipped kitchen is stocked with all the essentials—from appliances to cookware—so you can easily prepare family meals or your morning coffee. A full-sized washer and dryer are also tucked into this space for added ease during longer stays. The dining area comfortably seats six and flows seamlessly into the open-concept living room, where you’ll find a cozy sleeper sofa and direct access to a private back patio. Additional seating is available at the breakfast bar, perfect for casual meals or entertaining.brbrUpstairs, the spacious master suite offers a peaceful retreat with a plush king-sized bed, a luxurious double vanity, and a walk-in tiled shower for a spa-like experience. Just outside the master bedroom, a versatile loft area doubles as a home office or game room and features a game table along with a second sleeper sofa—great for kids, guests, or extra lounging space.brbr Highlights:br2 Bedrooms | 2 Bathrooms | Sleeps 8brbr- Master bedroom upstairs with king bed, double vanity, and walk-in showerbr- Twin bedroom on main floor with shared en-suite accessbr- Modern bathrooms with stone countertops and elegant finishesbr- Sleeper sofa in living room and additional sleeper in upstairs loftbr- Loft space perfect for games, work, or winding downbr- Open-concept main living area with comfortable furnishingsbr- Fully equipped kitchen and dining area for meals at homebrbr*The house is located in Sea Pines gated community that requires a car pass. Guests are required to purchase a weekly rental, car pass at the main gate for $20 in CASH only.

2904 - 2 BD Sea Pines Villa w/ Pool & Fairway View

Hilton Head Island, South Carolina, United States

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