Vacation Home Rentals By Owner In Hilton Head Island, SC

$1009.1

4th Row Ocean on Beach Path - Dog Friendly - Private Pool - Sea Pines Home

Hilton Head Island, South Carolina, United States

Welcome to 14 Canvasback Road - a newly renovated five-bedroom, four-bath home located 4th row ocean in Sea Pines, directly on the beach path for easy access to the beach with carts, beach chairs and beach towels. brbrLocated just inside the Ocean Gate on a quiet cul-de-sac, 14 Canvasback Road features a private pool, can accommodate up to 14 guests and is designed for comfort, family dining and easy coastal living. brbrThis home welcomes up to two dogs with prior approval. A pet fee applies and must be arranged & confirmed in advance with us.brbrEnjoy your private pool, recently refinished and offering complimentary seasonal heat (weather permitting, see more details below). An expanded deck provides plenty of space to relax after beach days and the new Weber grill allows for easy family cookouts. New outdoor hot/cold shower and utility spray area for all beach supplies is right outside the pool deck. brbrThe open, updated chef’s kitchen is fully equipped with everything you’ll need to cook for your family - modern appliances, two sinks, 6-burner gas range, built-in beverage/wine fridge, easy access pantry closet and a large island with bar seating beneath high ceilings and a skylight—ideal for gathering and shared meals. Two separate living areas allow groups to watch different TVs but still be together. A new light-filled four-season room with additional dining seating for four overlooks the pool and opens directly to the deck and beach path, creating seamless indoor-outdoor living. brbrWhether you’re planning a family beach vacation, a group getaway, or traveling with your dogs, 14 Canvasback Road offers the space, comfort, and location to make your Sea Pines stay unforgettable.brbrbr**Bedding Configuration**brbr• Bedroom 1: King (Master #1, First Floor, Flat Screen TV, Private Bath) brbr• Bedroom 2: Two Doubles (First Floor, Flat Screen TV, Private Bath)brbr• Bedroom 3: King (Master #2, 2nd Floor, Flat Screen TV, Private Bath)brbr• Bedroom 4: Two Queens (2nd Floor, Flat Screen TV, Shared Bath)brbr• Bedroom 5: Twin Bunk Bed (2nd Floor, Flat Screen TV, Shared Bath)brbrbr**Additional Information**brbr• Distance to Beach: 4th Row Ocean – Located Directly on the Beach Path – Less Than a Three Minute Walkbrbr• Private Pool: The pool is approximately 26' by 13'. The pool is able to be heated seasonally only at no additional cost. The pool cannot be heated if temperatures drop below 55 degrees at any point during your stay, and it is not available during the summer months. Pool heat is typically available March-May and September-October, weather permitting.brbr• Dog Friendly: This home permits a max of two dogs to stay in the home. The pet fee is $250 plus tax – please reach out to our office in advance to confirm and pay the additional pet fee.brbr• Fully Equipped Kitchen w/ a Keurig & Regular Drip Coffee Makerbrbr• 8 Beach Towels, 12 Beach Chairs, 3 Wheeled Beach Cartsbrbr• High-Speed Wi-Fibrbr• Newly Renovated & Updated Throughout brbr• Main-Level New LG Washer + Dryerbrbr• 7 Smart Televisions Throughout the Homebrbr• 2,785 Square Feetbrbr• Paying guest reservations staying between 4-27 nights will receive a $250 VayK Life beach/bike gear credit. This will be emailed to you after making a reservation and is valid for VayK Life rentals only.brbr• Parking: There is parking available at the home for up to four cars max. Not all can be large SUVs due to the size of the driveway. The garage can fit one car and three smaller cars can fit in the driveway. Parking passes are an additional $17/pass per week.brbrHilton Head Island Short Term Rental Permit #29187

Bed

Bath

Sleeps

$419.13

/ Nightly

Private Vacation Home

Co Co's Island Treehouse steps to Harbourtown! Pet Friendly with large deck.

Hilton Head Island, South Carolina, United States

This secluded, cozy treehouse is perfect to relax in while just steps away are all the amenities of the famous Harbourtown located inside Sea Pines Resorts boosting beaches, biking trails, shops and restaurants.The huge deck features both fire pit and grill. Tucked away in the lower level, down the interior Spiral Staircase,( picture perfect but watch your step.. ) is a private work area. You will truly feel transported to a place of serenity. brAfter a day of fun and sun, this oasis nestled in the trees provides an ideal space to cool down, watch the deer go by or tune in to your favorite TV show on the 85 smart TV from the Old School ,fall asleep fast, recliner. Maybe you want to try the original Japanese soaking tub. You will love sleeping in utter stillness in either King bed away from the hub-bub of Hilton Head. You will be on your own island...Deer Island! Google it.. It's real.brIf it happens to rain , there is a sheltered spot under the canopy of the house to eat or twirl in the hanging chairs.brbr

Bed

Bath

Sleeps

$1171.17

/ Nightly

Private Vacation Home

5 ⭐️ property! Private pool!!SHORT walk to beach!! ❤️ of Sea Pines. Sleeps 12

Hilton Head Island, South Carolina, United States

This Sea Pines private oasis meets every need for your vacation with family or friends. One of the largest private pools in Sea Pines looks out over the serene tidal marsh and the beach is 0.4 mile away. Pool heater is available in cooler months.brbrThe 5 bedroom home welcomes up to 12 guests with a less than 5 minute bike ride or 8 minute walk to an uncrowded beach. On the main level you will find multiple large living spaces. brbrThe entryway leads you to the first living room with comfortable seating and a 65 TV. From here you can view the large bright dining area. The kitchen is a chef's dream with gas range, granite counter tops, large island with seating for 4, convection oven, warming drawer, stainless refrigerator and bonus standalone freezer that helps minimize trips to the grocery. The kitchen leads to another living/game area with huge sectional, large tv, game/dining table for four. The dining room holds a large table with seating for 8 or add chairs for extra seating. brYou can enjoy your coffee or evening cocktails on the screened porch with comfortable lounging and high top dining table. The large back deck is the perfect place to soak in the sun and prepare dinner on the gas grill. (Also, keep an eye out for deer who usually make an appearance each evening.). The expansive pool deck includes multiple loungers, dining table and umbrella. It includes one of the larger private pools in the area.brbrDownstairs you will also find a beautifully decorated King suite bedroom and bathroom.brbrUpstairsbrUpstairs are the additional 4 bedrooms, 3 bathrooms and laundry room.brbr1 King - The private King suite includes large seating area including two comfortable club chairs and separate desk area. The ensuite bathroom includes double vanities, walk-in dual head shower and multiple closets for storage.brbr1 Queen Bedroom brbr2 Extra Long Twin Bedroombrbr2 Sets of Twin Bunks Bedroom (4 beds in total) brbrBathrooms - 2 conveniently located hallway bathrooms each with large vanities, tub and showerbrbrThe home is also near a communal playground. Beach chairs, beach towels, pool floats and board games are provided. brbrExtras include complimentary Wi-Fi, cable, and a dry bar. High speed internet makes it easy for work if you have to! brbrParking is available for up to five cars in the driveway. brbrGate/vehicle passes are required to gain access to Sea Pines and are available for purchase upon arrival at the security gate for $10 for a daily pass or $30 for a weekly pass per vehicle. br

5

Bed

4

Bath

12

Sleeps

$735.66

/ Nightly

Private Vacation Home

Escape to Coastal Elegance at 259 Greenwood Drive

Hilton Head Island, South Carolina, United States

Discover your next favorite getaway—a flawlessly renovated Sea Pines retreat where modern luxury meets laid-back Lowcountry living. Spanning 2,742 sq ft, this thoughtfully updated 4-bedroom, 3-bath home offers vaulted ceilings, dual living areas, a wet bar, and a chef-ready kitchen. Cozy up indoors or breeze into the screened porch and expansive paver patio, complete with an outdoor kitchen overlooking the Atlantic Dunes Hole 8 lush golf fairway vistas.brbrSteps from the Sea Pines Beach Club Trolley Parking Lot, Harbour Town, and Sea Pines’ best attractions, this home promises both convenience and serenity. Elegant, spacious, and perfectly positioned—259 Greenwood Drive is set to become a standout short-term rental on Hilton Head Island.brbrTown of HHI STR Permit #64570brbrHIGHLIGHTbr• *Heated Pool & Spa. This pool & spa can be heated for an additional fee of $300 per week from March through November. The spa can be heated separately for an additional fee of $225. Please note that the electric heat pump only allows the pool to heat to “approximately” 20 degrees warmer than the lowest nighttime temperature.br• Golf Course View - Atlantic Dunes, Hole 8 Fairwaybr• 6 TVsbrbrSEA PINES RESORT FEATURES & AMENITIES [All Sea Pines Resort Features are subject to purchase, seasonality, and availability.]br• Lawton Stablesbr• Golf Courses - Harbour Town Golf Links home to the RBC Heritage Classic. Additional Sea Pines Resort courses include Heron Point by Pete Dye, Atlantic Dunes by Davis Love II, and Sea Pines Country Club [Private]br• Harbour Town Marina - Lighthouse, Shops, Restaurants, Water Activities, Private Boat Chartersbr• South Beach Marina - Shops, Restaurants, Water Activities, Fishing Charters, Dolphin Toursbr• Racquet Clubs - South Beach & Harbour Townbr• Trolley Transportation - Schedule Variesbr• Tower Beach Parking - Property Owners Onlybr• Sea Pines Beach Club Parking - Major Seasonality Restrictionsbr• Ongoing upgrades to enhance the resort include renovations, new construction, and road projects.brbrPROPERTY CONFIGURATIONbr• 4 Bedroomsbr• 3 Bathsbr• Sleeps 10br• Parking for a maximum of 4 vehicles. All vehicle parking must be located on improved surfaces, like driveways, and cannot be on grassed or landscaped areas.br• 2,742 square feetbr• Washer and dryerbr• Fully equipped kitchenbr• Gas GrillbrbrBEDDING CONFIGURATIONbr• Bedroom 1 - 1 King br• Bedroom 2 - 1 Kingbr• Bedroom 3 - 1 Kingbr• Bedroom 4 - Queen + Twin with Trundlebrbr**Please Note: Beach renourishment projects are currently underway and will continue through late spring. While work is active at times, the beach remains open for guests to enjoy and access the shoreline daily. We appreciate your understanding as the community works to enhance and preserve our beautiful beaches!brbrPROPERTY REMINDERSbr• Pets are not allowedbr• The fireplace is not for guests' use.br• *Heated Pool & Spa. This pool & spa can be heated for an additional fee of $300 per week from March through November. The spa can be heated separately for an additional fee of $225. Please note that the electric heat pump only allows the pool to heat to “approximately” 20 degrees warmer than the lowest nighttime temperature.br• * A total of 4 adult unisex bikes and a beach wagon are included in your amenity fee when booking. Not included with rentals over 21 nights.br• The Vacation Company's Guest Connect will contain all your check-in information (lock codes, Wi-Fi codes, and other information pertinent to your stay).

Bed

Bath

Sleeps

$900.79

/ Nightly

Private Vacation Home

10 Min Walk to Beach; Private, Heatable Pool in Secluded Backyard; Fabulous Kids' Bunk Room!

Hilton Head Island, South Carolina, United States

Love the beach but want privacy & serenity too and a private pool for your kids to splash & play Welcome to Sailors Cove, which is a family-friendly, beautifully renovated home that is a short, 10 minute walk to the beach. Your kids will LOVE this home, with its bunk room, private pool in the backyard and easy access to the fun activities within Sea Pines Resort. Sailors Cove is tucked away within the live oaks, sea pines, bamboo, palmetto trees and other maritime forest vegetation, providing a very private & well-screened backyard retreat. The well-stocked kitchen and multiple indoor & outdoor gathering areas make this home an excellent getaway for extended family or friends. brbr brbrSea Pines Resort is an award-winning destination for family vacations & getaways. You can either sit back, relax and enjoy the stunning Lowcountry scenery with Spanish draped live oak trees, saltwater marshes, palmetto trees, sandy beaches and lagoons or you can pack in as many sports, water & outdoor activities as you and your family can handle. Boasting golf courses, tennis facilities, hiking trails, boating & water adventures and more, this Hilton Head Island resort, which is tucked away amidst the maritime forest between the Atlantic Ocean and Calibogue Sound, is the ultimate retreat. Be sure to explore the Sea Forest Preserve, the Lawton Stables, Sea Pines Beach Club, Heritage Farms as well as the restaurants & shops at Harbourtown. brbr brbrSLEEPING ARRANGEMENTS FOR SAILORS COVE (sleeps 11): brbr brbrMaster Suite (located on the lower level): brbr brbr- King bed brbr brbr- Night stands with wall sconces brbr brbr- Dresser with smart TV brbr brbr- En-suite bathroom with double sink vanity and walk-in shower brbr brbr- Sliding door access to the back deck brbr brbrSecond King Suite (located on the lower level): brbr brbr- King bed brbr brbr- Night stands with reading lamps brbr brbr- Dresser with smart TV brbr brbr- En-suite bathroom with spacious vanity and walk-in shower brbr brbrThird King Suite (located on the lower level): brbr brbr- King bed brbr brbr- Night stands with reading lamps brbr brbr- Dresser with smart TV brbr brbr- En-suite bathroom with spacious vanity and walk-in shower brbr brbrKids' Bunk Room (located on the second floor): brbr brbr- Built-in bunk bed with two twin beds and three built-in twin beds. There are also three trundle twin mattresses beneath the built-in twin beds. brbr brbr- Wall-mounted smart TV brbr brbr- En-suite bathroom with spacious vanity and shower/tub combo brbr brbr*********** brbr brbrAMENITIES: brbr brbr- Live your best outdoor life in Sailors Cove's exquisite outdoor spaces, including a private pool, patio, back deck and screened porch. Backyard area is very private with the trees, shrubs & bamboo providing a screening from neighbors. (Pool can be heated for additional charges. Certain restrictions apply. Please contact us to arrange for the heat to be turned on a minimum of 48 hours prior to your arrival.) brbr brbr- Easy breezy 10 minute walk to the beach. brbr brbr- Three bedrooms with king beds and en-suite bathrooms. brbr brbr- Kid-friendly bunk bedroom with three built-in twin beds and a built-in twin bunk bed. brbr brbr- Fully-equipped chef's kitchen with granite countertops, vaulted ceilings and stainless steel appliances. brbr brbr- Gas BBQ grill. brbr brbr- Full sized washing machine & dryer. brbr brbr- Free WIFI; Roku streaming TVs (no cable) brbr brbr- Don't wait in an office to check-in or get a key! Drive straight to Sailors Cove and enter the front door with a secure electronic lock code. Prior to your visit, we will send you our mobile app with directions and full instructions. brbr brbr- No Saturday to Saturday Restrictions - MAY RESERVE LESS OR MORE THAN 7 NIGHTS!! brbr brbr*********** brbr brbrGuests initially enter Sailors Nook by walking up the exterior staircase from the driveway to the front porch and front door. Once you enter your code within the electronic door lock on the front door, you will enter the home's first floor, which features the kitchen, dining area, living room, screened porch and all three king suites. Walk up a flight of stairs to find the kids' bunk room suite. brbr brbrNO SMOKING. NO PETS. Tenant must be 25 years old. Reservations made for younger individuals will not be honored without any accompanying adult staying in the home at ALL times. NO PARTIES, EVENTS, PERFORMING ARTISTS OR BANDS ALLOWED AT ANY TIME. You may not exceed the maximum occupancy at any time — day or night. Fireplace and fire pit are NOT available for guest use. These are causes for eviction with no refund, and may damage our ability to offer the home for future guests exposing you to liability. This is a residential home -- please be respectful of our neighbors. brbr brbrPool is serviced weekly by a pool service company. It is NOT serviced on every arrival day. Storms and prior guests may mean it is not in pristine condition. brbr brbrFor TV apps, personal subscription required. brbr brbrHilton Head Island Short Term Rental Permit #028020 brbr brbr*********** brbr brbrSea Pines is a private gated community with very specific rules and regulations. A few of the restrictions are listed below but please access seapinesliving . com to read and download the complete listing. Motorcyles, motorhomes, recreational vehicles, trailers, golf carts, are not permitted in Sea Pines. Any nonconforming vehicle will be turned away by Sea Pines security. No weddings or events can be held on rental property premises. brbr brbrDue to limited parking availability at the Sea Pines Beach Club, the complimentary Sea Pines Trolley is available to take rental guests between designated stops and the Sea Pines Beach Club continuously during the hours of 9:00 AM – 5:00 PM. Between early March and Labor Day, rental guests will not be able to park at the Sea Pines Beach Club or Plantation Club overflow lot. More details can be found at seapinestrolley . com, and we will include information in the welcome packet provided with your reservation. brbr brbr*********** brbr brbrGuests staying at all ITrip Charleston & Hilton Head managed properties receive the following: brbr brbr* Amenity pack, starter set of soap, shampoo,brbrBook with confidence! We are Charleston & Hilton Head’s highest rated and most responsive large vacation rental agency. We have hosted over 40,000 great stays with an average guest review score of 4.9 out of 5! brbr brbrGuests under the age of 25 can only check in with a parent or official guardian. brbr brbrBookings are refundable up to 30 days prior to check in less a $200 Admin Fee. No refunds within 60 days. No refunds for travel, weather or other delays. Please purchase travel insurance. brbr brbrWe offer rental guests the right to participate in a limited damage waiver program. brbr brbrAll reservations subject to CLEAR ID security checks, completion of guest and car registration information and confirmation of understanding of all noise, parking and trash ordinances. brbr brbrPlease keep A/C temperature above 70F for optimal comfort. It is recommended to set it at 72F. Remember to keep doors and windows closed to maintain a cool home and keep bugs out. Fridges may take 24 hrs to cool when loaded after cleaning.

Bed

Bath

Sleeps

$1155.0

/ Nightly

Private Vacation Home

Heron Hideaway: Grand Marsh Home w/ Pool & Hottub

Hilton Head Island, South Carolina, United States

Welcome to The Heron Hideaway- your Luxury Hilton Head Getaway.brbrbrStay low country in this exclusively designed home. Newly remodeled & fully equipped for your golfer’s retreat or family/friends' coastal vacation. 5 mins from SeaPines Beach Club and 6 mins from the Harbourtown Golf Links. brbrbrLocated in famous Sea Pines Plantation. Enter the gates of resort living offering trolley rides to local restaurants, premium golf courses, pool access, HarbourTown Lighthouse, & most importantly- the beach!brThe spacebrCustom charcuterie board, wine/beer, fresh flowers, or private chef accommodations are available upon request. Perfect for special occasions upon arrival or for an after-round or beach snack. brbrbrPrivate pool and hot tub. Pool heating:brDue to heating costs, we cannot heat the pool in Dec. or Jan. brApril-May $75 per night brNove-Feb $125 per night. br Hottub is already heated and is of course, free.br**Due to costs of natural gas and size of the pool we cannot offer any discounts for a pool heating fee. brbrThe home features a Level 2 EV Charger in the garage for your convenience. Compatible with EV and PHEV models. brbrA chef’s kitchen opens into the living room with a gas fireplace for cozy nights in. A functional layout boasting 4 bedrooms and 4.5 bathrooms- featuring four ensuites, 1 located on the main ground floor, and three bedrooms upstairs. In the garage, you will find family-fun games! Including a ping-pong table (paddles & balls included), a PacMan machine, 2 sets of pickleball racquets and balls, AND MORE! brbrbrBedrooms:brThe bedrooms feature comfortable luxury-style bedding.brbrbrBedroom #1-Downstairs Master featuring a King bed, ensuite master spa bathroom with a free-standing soaking tub, walk-in shower, walk-in closet, and private access to the back patio. Sleeps 2. brbrBedroom #2- 2nd Upstairs Master featuring a King Bed, ensuite bathroom with a soaking tub, walk-in shower, walk-in closet, and private access to upstairs balcony overlooking the pool and marsh. Sleeps 2. brbrBedroom #3- Located upstairs and features two Twin trundle beds with an ensuite bathroom, a walk-in shower, and spectacular views of the marsh. Sleeps 4. brbrBedroom #4- Located upstairs featuring a Queen Bed, ensuite bathroom with a walk-in shower, walk-in closet, and private access to upstairs balcony overlooking the pool and marsh. brbrbrBathrooms:brEach bathroom features oversized spa plush bath towels, washcloths, makeup cloths, non-toxic cleansers, and a hairdryer.brbrbrBathroom#1-Located in Master. Custom tile shower with a free-standing soaking tub and double vanity. brbrBathroom #2- Located in the Upstairs Master. Custom tile, soaking tub, walk-in shower, and double vanity. brbrBathroom #3- Located in the Twin bedroom. Custom tile, single vanity, and walk-in shower. brbrBathroom #4- Located in the Queen bedroom. Custom tile and walk-in shower. Fan runs 24 hours to prevent any moisture build-up. brbrBathroom #5- Haf bath powder room located off the living room area. brbrLiving Room:brThe living room offers a 65 Smart TV, features cable, a cloud-like couch, reading materials, fun board games, and a gas fireplace to create a cozy at-home ambiance with an option with or without heat. Views of the pool, hottub, and marsh can be enjoyed while lounging in any seat in this room!brbrKitchen:brOffers a fully equipped chef's kitchen to make homemade meals with state-of-the-art WOLF appliances, pots/pans/kitchenware, and complimentary local organic coffee, teas, spices.brbrBackyard:brBack patio with a fire pit to gather around on cooler nights, an outdoor (hot and cold water) rain-head shower, an outdoor grilling area, a private spa like hottub that seats 7, heated pool, loungers, and outdoor dining area. brbrBeach Equipment: br4 Beach Cruiser Bikes are located at the house free of charge. 4 Tommy Bahama backpack beach chairs and 10 beach towels are also available. brbrAdditional beach equipment can be rented from the Sea Pines Beach Club.brGuest accessbrbrYou will receive check-in instructions via email from VRBO a few days before your arrival. These instructions will be available anytime in the app in your reservation under Check-In Instructions. brbrParking is allowed in the driveway and garage ONLY. NO parking on the grass, roadside, or in the pinestraw. Sea Pines actively enforces this and can fine for these violations.brOther things to notebrLandscapers come every Friday to maintain the grounds. brbrThe trash company comes every Wednesday and Saturday to get trash bags out of the bins located in the service yard. The trash MUST be placed in bags in order for them to take it.

4

Bed

4

Bath

10

Sleeps

$550.51

/ Nightly

Private Vacation Home

3 Bedroom retreat with private pool

Hilton Head Island, South Carolina, United States

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.brbrTucked away on a quiet street in the heart of Sea Pines, 10 Battery Road is a charming coastal retreat designed for both relaxation and connection. With its bright open design and multiple areas to gather, this single-story home invites guests to unwind and enjoy every corner.brbrThe formal living room sets the tone with soaring cathedral ceilings and a wall of windows overlooking the private pool. Just steps away, a cozy den with leather seating and direct pool access creates the perfect spot for movie nights or quiet afternoons. The kitchen, updated with granite counters and a stylish backsplash, flows seamlessly into the dining room, where a table for six is complemented by a casual sitting area for relaxed conversations or evening downtime. A tucked-away desk offers a convenient spot for catching up on work when needed.brbrBedroom 1, the spacious primary suite, features a king bed, a day bed with a twin trundle, and a newly renovated bathroom with dual sinks and a walk-in shower. Bedroom 2 offers two twin beds with hall access to a bathroom with a shower and tub combination, making it perfect for younger guests or friends. Bedroom 3 includes a queen bed with nearby access to a full bathroom and walk-in shower. brbrOutdoors, the private pool is surrounded by lush landscaping and a brick patio, creating a secluded tropical oasis. Comfortable seating and a gas grill make it ideal for sunny afternoons, family cookouts, and long evenings under the stars. Whether enjoying a round of golf at nearby Harbour Town, exploring the natural beauty of Sea Pines, or simply soaking up the coastal atmosphere by the pool, 10 Battery Road offers the perfect setting for a memorable Hilton Head escape.brbrKey Features:brbr- Proximity to the beach: 10 min bike ridebr- Private Poolbr- Sea Pines Resort Amenitiesbr- Pets are not allowedbrbr- The pool can be heated for an additional charge, give us a call for heating rates and to make arrangements. Pool 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.brbrRent price includes: Rental Rate, Hospitality Program, Beach Gear Credit, Booking Processing Fees, and Departure Clean. Your Luxury Concierge is included with no additional cost.

3

Bed

3

Bath

9

Sleeps

$931.22

/ Nightly

Private Vacation Home

5 bedroom luxurious retreat overlooking the lagoon

Hilton Head Island, South Carolina, United States

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head.brbrThis custom-built home in Palmetto Dunes offers the perfect balance of comfort and convenience. Just a ten-minute walk to the beach, the home is spacious, meticulously maintained, and designed for families and friends to gather and relax.brbrInside, the entryway opens to soaring fourteen-foot ceilings, a formal living room ideal for quiet conversation, and a formal dining room with seating for ten. The great room serves as the hub of the home with its high ceilings, built-in entertainment center, sixty-five inch smart TV, a sleeper sofa, and triple French doors leading to the back deck. Overlooking this space is a gourmet kitchen complete with stainless steel appliances, double wall ovens, a five-burner cooktop, granite countertops, new cabinetry, and additional seating for up to 8 guests. The adjoining breakfast room provides seating for ten with tranquil views of the lagoon, where you may spot egrets, herons, and osprey in the morning.brbrThe home offers 5 bedrooms and 4.5 bathrooms, with a layout designed to maximize both privacy and flexibility. Bedroom 1 is the primary suite with a king bed, a fifty-inch TV, and French doors opening to the deck with lagoon views. Close by is Bedroom 2, a small twin bedroom that makes the space ideal for children. Bedroom 1 and Bedroom 2 share their own ensuite full bathroom. Bedroom 3 is the second primary suite, set on its own elevated level for quiet privacy, featuring tropical Tommy Bahama furnishings, a king bed, large windows with front yard views, and a beautifully tiled en-suite bath. On the opposite side of the home, Bedroom 4 includes a queen bed and an ensuite full bath, while Bedroom 5 offers both a queen bed and a bunk set with a twin trundle, also with its own ensuite bathroom.brbrThe south-facing backyard is open and sunny, offering beautiful views of the fifteen-acre spring-fed lagoon with its abundant birdlife. The pool is a highlight, much larger than most in the area, with an eight-foot deep end, an eight-inch sun shelf, and a four-foot-wide shear flow fountain. The chlorinated pool is accented by colored LED lights and a three-dimensional tile dolphin. A large lawn, paver pool deck with plenty of furniture, and a renovated twelve-by-thirty-foot deck with dining space for eight, umbrellas, and a gas grill complete the outdoor setting.brbrFor a bit of extra fun, the garage includes a foosball table, making it a great spot for friendly competition during your stay.brbrKey Features:br- Private Poolbr- The pool can be heated for an additional charge, give us a call for heating rates and to make arrangements. Pool 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- Lagoon Viewbr- Foosballbr- Palmetto Dunes Amenitiesbr- Palmetto Dunes Dune Buggy Transportation: Available April - September for free transportation throughout Palmetto Dunes and Shelter Cove. For more information on Pickup & Drop off times/locations, please callbr- Pets are not allowedbrbrRent price includes: Rental Rate, Hospitality Program, Beach Gear Credit, Booking Processing Fees, and Departure Clean. Your Luxury Concierge is included with no additional cost.

Bed

Bath

Sleeps

$1177.0

/ Nightly

Private Vacation Home

Winter Golf Special - 6 BR Luxury Home-Private Pool in Hilton Head-Pets Welcome!

Hilton Head Island, South Carolina, United States

Welcome to your perfect luxury getaway in Hilton Head, SC, nestled within the exclusive Palmetto Dunes gated community. This charming home offers a blend of relaxation & adventure, situated less than a mile from the beach & a short distance from dining, shopping, & marina activities at Shelter Cove. With direct access to an award-winning tennis center, pickleball courts, and an extensive 11-mile lagoon system for kayaking & canoeing, you’ll find many opportunities for outdoor fun right at your doorstep.brbrUpon entering the front door, the main floor captivates with its spacious design and classy coastal decor. The large open living room complete with a 65 TV seamlessly flows into a well-equipped kitchen, complete with a breakfast table and additional island seating. A separate dining room provides an intimate space for formal gatherings. The main floor also boasts 3 expansive king bedrooms, each with en-suite bathrooms. There is an additional powder room for guests to use the restroom that is not associated with a bedroom. Each bedroom on our main floor is complete with brand new furnishings and a smart tv in each room!brbrHeading up the staircase to the second floor, you'll find 3 additional bedrooms and a large shared bathroom. The first guest bedroom offers two comfortable queen beds. The second guest bedroom is designed with kids in mind, housing two bunk beds with twins over twin very comfortable mattresses. The third guest bedroom is furnished with two comfortable queen beds. Each bedroom on our second floor is complete with brand new furnishings and a smart tv in each room!brbrStepping outside, a large back porch awaits, complete with a grill and an outdoor table that seats six. This alfresco dining area provides the perfect setting for enjoying meals amidst the picturesque surroundings. Overlooking the expansive pool and 11 mile lagoon, the outdoor space is a haven of relaxation and recreation. Whether you're basking in the sun, enjoying a refreshing swim, or unwinding in the afternoon and evening hours, the outdoor amenities complement the luxurious atmosphere of your gated community vacation home.brbrThe 11-mile lagoon is owned by Palmetto Dunes Property Owners Association (PDPOA) and is overseen by the Lagoon & Lake Advisory Group. Due to high salinity levels, fish are unable to reproduce and the lagoon is restocked with 11-inch fingerlings annually. The lagoon is intended for the enjoyment by Palmetto Dunes and Leamington property owners and their invited guests. Approved activities include boating, kayaking, canoeing, fishing and crabbing. Paddleboards and swimming in the lagoons and lakes are prohibited. If you enjoy wildlife, The lagoon is home to forty species of birds and fish, so bird watchers may spot bald eagles, osprey and great blue herons while those interested in fishing will find schools of red fish, sea trout, flounder, black drum and tarpon. the lagoon offers some of the best fishing in the country with a record 58 pound red fish being caught in 1987. brThis meticulously designed retreat promises an unforgettable vacation experience, combining opulent interiors with resort-style outdoor living. Welcome to your private oasis in the heart of an exclusive gated community.brbrFor over five decades, Palmetto Dunes in Hilton Head, SC has stood as an example of what a commitment to an exceptional golf experience can mean. It’s a combination of three magnificent courses and customer satisfaction that is second to none. The heart of Palmetto Dunes golf beats in the three legend-built courses that surround the golf resort, and while layouts may challenge, the experience always satisfies. Book your golf experience at the Robert Trent Jones course, the Arthur Hills course, or the George Fazio course today! Learn about booking online for best savings!brbrHome Overview:brbrFirst FloorbrBedroom 1: 1 King (private bath)brBedroom 2: 1 King (private bath)brBedroom 3: 1 King (private bath)brbrSecond FloorbrBedroom 4: 2 Queens (shared bath)brBedroom 5: 2 Twin over Twin Bunk Beds (shared bath)brBedroom 6: 2 Queens (shared bath)brbrAdditional Features:brSquare Footage: 3,414brPool size: 16x12brOutdoor Parking Spaces: 5-6brPool Heat – Yes, inquire about feebrInterior Garage: Perfect for storage of bikes, trailers, beach gear, coolers, golf clubs. etc.brNeighborhood: Palmetto DunesbrbrDistances:brBeach: 0.8 mibrColigny: 5.6 mibrHarbor Town: 7.9 mibrSouth Beach: 10.2 mibrShelter Cove: 1.9 mibrbr** Palmetto Dunes Rules and Regulations**brbr- Decals must be properly affixed and passes visible at all times. br- Vehicles without a displayed pass or decal may be cited.br- Parking on roadways or in yards is not permitted.br- Motorcycles are prohibited.br- Cyclists and pedestrians shall use leisure paths where available. Automobiles have the right of way.br- Electric boats belonging to property owners are permitted on lakes and lagoons. Gas engines are prohibited.br- No swimming in lakes or lagoons.THIS IS WHERE THE GATORS LIVEbr- Loud music or excessive noise is not tolerated at any time.br- ALLIGATORS ARE DANGEROUS. State law prohibits any person from feeding, enticing, or harassing alligators.br- Do not feed wildlife of any kind in Palmetto Dunes.br- Absolutely NO hunting or shooting!br- Absolutely no fireworks!br- Towels and swimwear may NOT be hung on porch railings.br- Trash cans must remain in the service yard for pickup. Do NOT bring them to the street.

Bed

Bath

Sleeps

$449.93

/ Nightly

Private Vacation Home

Sea Pines Home - Walk to the Beach! Lagoon View + Pool

Hilton Head Island, South Carolina, United States

NEW to VRBO! ISLAND LIFE is a charming 3/2 Sea Pines Bungalow - a short walk to the beach/next to neighborhood pool! Nestled just inside the Ocean Gate, this retreat stands alone on an oversized wooded lot! Enjoy a private balcony that overlooks a large, natural lagoon that is teeming with wildlife!brbr● Short Walk or Bike to Beach!br● 3 bedrooms / 2 bathbr● Private Home - big Wooded Lotbr● On Wildlife Lagoonbr● Next to Poolbr● Family Friendlybr● 4 SmartTVsbr● PS4br● Beach Gear Providedbr● SuperhostbrbrNEW TO THE VACATION RENTAL MARKET!brbrIsland LifebrA free-standing Beach Bungalow In the Heart of Sea Pines - Quick walk to the Beach & steps to the Pool! brbr● Book with confidence - Mike has earned Superhost status 6 years in a row!brbr● Summer months are starting to book up - don't wait to reserve your summer vacation - Book 7 or more nights and automatically receive 10% off the nightly rate!brbrIf you are considering staying here: Press ❤ on the upper right corner to save our listing so you can easily return to book!!!brbrbr●●● HOUSE AMENITIES ●●●brbrUpon your arrival at Island Life, you'll find private, paved parking for two vehicles leading directly to your home’s front staircase and keyless entry. For convenience & safety, the area is lit up at night!brbr● LIVING ROOM: The bright & airy coastal-chic living room features a classic shiplap vaulted ceiling which is conveniently open to the kitchen/dining area. Savor the wildlife and natural beauty of the private lagoon from the large windows. Snuggle up on the large sectional while streaming your favorite movies on our 70” SmartTV or have an epic family game night with the large collection of classic board games. All while staying connected with our high-speed internet WIFI!brbr● KITCHEN: Prepare home-cooked meals in a thoughtfully equipped kitchen that features premium cookware and utensils. Other kitchen amenities include a large island with countertop seating for 4 (more seating on the nearby table), a Jenn-Air cooktop and oven, full-size refrigerator with an ice maker, dishwasher, and a coffee bar with both a drip coffee maker & Keurig!brbrBEDS: br3 Queen Bedsbr1 Twin Bedbr1 Pack & Play Bedbrbr● PRIMARY BEDROOM: Features a classic shiplap vaulted ceiling, a comfortable queen bed with a premium mattress, blackout shades for better sleep, a 32” Smart TV, spacious closets, and an attached bathroom with shower and soaking tub.brbr● GUEST BEDROOM: Roomy with a classic shiplap vaulted ceiling, another queen-sized bed with premium mattress, blackout shades for better sleep, a 43” Smart TV, two closets, and a full shower bathroom right outside the door!brbr● LOFT: For the young at heart, or families with children, a cozy loft awaits. Climb the winding staircase to find a delightful space with a Twin-over-Queen bunk bed, wall-mounted Smart TV equipped with a Sony PlayStation, and a selection of PS4 games!brbr● TECHNOLOGY: Stay connected and entertained with Spectrum high-speed WIFI - measured at 355 Mbps! Enjoy streaming services & apps like Netflix, Amazon Prime, Hulu on the 4 SmartTVs (bring passwords). Kids will enjoy the PS4 & Games found in the loft!brbr● QUICK BEACH ACCESS: Beach access is a short walk or a two-minute bike ride on the nearby Beach Path 46 - enabling your group to quickly be on the white sand beaches of the Atlantic!brbr● BEACH & POOL EQUIPMENT SUPPLIED: When you're ready for a beach day, check out the ground-level storage, or Gear Room, which contains a beach umbrella, beach chairs, a rolling ice chest, pool noodles, pool rafts, boogie boards, and pool toys! Use the convenient beach cart to easily transport everything! Beach Towels also supplied as a courtesy. When you return from the beach, you can rinse sand off using the convenient outdoor shower area!brbr● BBQ provided below the house. Relax outdoors and grill food for family and friends! brbr● POOL: Island Life is conveniently located next to our neighborhood's sparkling pool. Grab some of the included pool toys from the Gear Room and relax on one of the lounge chairs. The pool is open year round! brbrbrbr●●● SEA PINES RESORT AMENITIES ●●● brbrAs a guest at Island Life, you will enjoy access to the first-class Sea Pines Resort amenities listed below, including the Sea Pines Beach Club - a five-minute bike ride away!brbr● 3 Championship Golf Courses: Play on renowned courses like Harbour Town Golf Links, Heron Point by Pete Dye, and Atlantic Dunes by Davis Love III.brbr● Beaches: Enjoy 4.6 miles of pristine Atlantic beachfront for relaxing and water activities.brbr● Biking and Nature Trails: Explore over 15 miles of trails through lush landscapes for biking and leisurely strolls.brbr● Nature Sanctuary: Immerse yourself in the beauty of the Sea Pines Forest Preserve, a haven for hiking and wildlife enthusiasts.brbr● Dining: Savor a wide range of culinary delights at our excellent dining establishments, catering to various tastes and preferences, and for every budget.brbr● 2 Marinas: Discover the Harbour Town Yacht Basin for water sports, boating, numerous restaurants and breathtaking views! Visit the South Beach Marina’s famous Salty Dog restaurant!brbr● Tennis: World-class tennis facilities cater to players of all skill levels.brbr● Shopping: Browse the many Sea Pines boutique shops and local markets for unique finds and souvenirs.brbr● Equestrian Adventures: The Equestrian Center offers horseback riding and equestrian activities for all ages.brbr● Water Fun: Many local companies offer kayaking, paddle boarding, fishing & more in the serene waterways surrounding the resort.brbrbr●●● EXPLORING HHI & SURROUNDING AREA ●●●brbr● HILTON HEAD ISLAND features 12 miles of pristine beaches, sunsets over the Inland Waterway & marshes, 24 golf courses + the RBC Heritage Golf Tournament at Sea Pines! Hundreds of restaurants (Southern food and drinks enjoyed with water views!), brew pubs and food trucks, Hilton Head Distillery, boating, zipline, chartered fishing trips (Great White encounters!), arts, culture & history, waterfront activities, marinas, nature trails, wildlife, Mitchelville (first self-governed freedman’s town in US), historic Civil War landmarks, coastal nature preserves, Gullah-Geechee history, golf, kayaking, tennis, yoga, scenic biking trails & biking on the beach!!, paddle boarding, kite-surfing, music events, horseback riding on the beach, huge outlet mall just off-island & more!brbr● Old Town Bluffton is right off-island with its historic neighborhoods, many restaurants & shopping opportunities, including 2 outlet malls.brbr● Historic Beaufort - Restaurants, Civil War history, Antebellum home tours & beautiful water views!brbr● Beautiful Historic Savannah is only 35 miles away brbr● Beautiful Historic Charleston (restaurants, museums, waterfront) is a 2 hour drivebrbrWe will send all this information & more 1 week before your arrival!

Bed

Bath

Sleeps

$422.36

/ Nightly

Private Vacation Home

New Listing!! Lovely three bedroom home in Sea Pines Hilton Head. New addition.

Hilton Head Island, South Carolina, United States

The house is three bedrooms and easily sleeps eight. Master bedroom has king bed . Second bedroom has two queen beds. Third bedroom has private entrance and en suite bathroom. Murphy bed. Each bedroom has its own full bathroom. Large living room and dining area, as well as full kitchen. New granite counter tops to be installed in May . Two decks overlook the Forest. The neighborhood is in Greenwood Forest Sea Pines. This neighborhood has its own private pool and tennis court. Home has 3 TVs and a piano. WiFi .Ten minutes by bike to South Beach. Five minutes to Harbourtown . Access to tennis and golf as well as bike paths. House is 1900 square feet. Washer/dryer. Air conditioner/ heat. Fully furnished. Will rent to owners of dogs . Eat in kitchen. All new flooring. new addition.

Bed

Bath

Sleeps

$2393.8

/ Nightly

Private Vacation Home

MyStay at 14 Laughing Gull – Premier Oceanfront Estate in Sea Pines

Hilton Head Island, South Carolina, United States

Set along one of the most breathtaking stretches of coastline in Sea Pines, 14 Laughing Gull is a private oceanfront estate designed for elevated gatherings, multi-generational stays, and effortless luxury. With expansive living spaces, seven bedrooms including a private apartment, and direct beach access, this home delivers a true Hilton Head retreat at scale.brbrWHY YOU’LL LOVE THIS HOME:brbr- Prime oceanfront location in Sea Pinesbrbr- Heated pool + spa (complimentary heat)brbr- Private beach path through the dunesbrbr- Sleeps up to 18 guestsbrbr- Seven bedrooms including private apartmentbrbr- Multiple living and dining areasbrbr- Chef’s kitchen overlooking pool and oceanbrbr- Outdoor kitchen + screened loungebrbr- Private primary wing retreatbrbrOCEANFRONT LIVING:brThe main living spaces are designed for gathering and celebration. An expansive living room filled with natural light flows into formal and casual dining areas, creating space for both large dinners and relaxed evenings. The chef’s kitchen features high-end appliances and generous prep space, all overlooking the oceanfront pool and lawn. A screened lounge and outdoor kitchen extend the living space seamlessly outdoors.brbrPRIMARY WING RETREAT:brThe downstairs primary wing offers privacy and refinement, complete with a king suite that opens to a secluded porch. Dual en-suite bathrooms, an expansive walk-in closet with custom built-ins, and a peaceful courtyard create a true sanctuary within the home.brbrSECOND LEVEL SUITES:brUpstairs, three oceanfront suites are connected by an open walkway overlooking the formal living room. Each bedroom features its own private balcony with sweeping views of the Atlantic, offering quiet spaces to begin and end each day.brbrBUNK ROOM AND OFFICE KING:brA few steps up from the main level you will find the bunk room with 1 twin bunk bed and 2 additional twin beds. Kid-Friendly games are also available in this room. Also, tucked behind the large office is an additional sleeping space with a queen bed for the `workaholic` of the group!brbrADDITIONAL PRIVATE APARTMENT:brA full private apartment includes its own living room, kitchen, king bedroom, and full bath — ideal for grandparents, in-laws, teens, or guests desiring additional independence.brbrOUTDOOR EXPERIENCE:brThe heated pool and spa sit just above the shoreline, blending into panoramic ocean views. A wide lawn leads to your private beach path, providing effortless access to Hilton Head’s iconic white-sand beach. Whether poolside, oceanside, or relaxing on the screened sleeping porch, every space is designed to embrace the coastal setting.brbrSLEEPING ARRANGEMENTS (Sleeps 18):brBedroom 1 – King primary suite (downstairs) with dual en-suite bathroomsbrBedroom 2 – King with en-suite bath (Blue Room)brBedroom 3 – King with en-suite bath (Peach Room)brBedroom 4 – Two Queen beds with en-suite bath (tub + walk-in shower)brBedroom 5 – Queen bed with bathroom (Office Queen)brBedroom 6 – Two Twin-over-Twin bunk beds with hall bathroombrBedroom 7 – Private apartment with King bed, kitchen, and full bath with walk-in showerbrbrTHE MYSTAY DIFFERENCE:brMyStay redefines the vacation rental experience through effortless stays and genuinely personal hospitality. We believe service should feel welcoming, not corporate — rooted in trust, care, and real connection. Our hands-on local team combines thoughtful touches, professional standards, and responsive support to ensure every stay feels seamless from arrival to departure. With MyStay, you’re not just booking a property — you’re experiencing hospitality done the right way.brbrIMPORTANT NOTES:brbr- This home does not allow Saturday check-ins or check-outs. Please inquire for additional information.brbr- Two weekly Sea Pines gate passes included. Additional passes must be purchased in advance.brbr- Primary renter must be 25+brbr- Private pool heat is complimentarybrbr- Pack ’n Play and high chair available upon advance requestbrbrTown of Hilton Head Island STR Permit #071134

Bed

Bath

Sleeps

$496.63

/ Nightly

Private Vacation Home

25 Wildwood Rd: Pet Friendly Sea Pines Home. 3 Beds. 2 Bathrooms. Sleeps 9.

Hilton Head Island, South Carolina, United States

Proudly hosted by Island Rentals of Hilton Head, 25 Wildwood offers the perfect blend of comfort, style, and convenience in the desirable Greenwood Forest neighborhood of Sea Pines. This contemporary coastal retreat features 3 bedrooms and 2 bathrooms, comfortably sleeping up to 9 guests. With polished wood floors, chic décor, and abundant natural light, the home feels both inviting and modern from the moment you step inside. The bright living room welcomes you with a spacious sectional sofa, cozy armchair, and 50 SMART TV, while floor-to-ceiling windows and glass doors open to a shaded deck complete with outdoor seating and a propane grill—ideal for relaxed afternoons and family barbecues.brbrThe open dining area, enhanced by a beautiful chandelier, leads seamlessly into the stylish kitchen, which features modern white cabinetry, stainless steel appliances, and eye-catching tile accents. A high-efficiency washer and dryer add extra convenience. The primary bedroom includes a King bed, large windows, a 42 SMART TV, and a luxurious ensuite bathroom with marble flooring and a glass-enclosed walk-in shower. Two additional guest rooms—one with two sets of bunk beds and another with a King bed and its own SMART TV—share a beautifully updated hall bathroom with similar upscale finishes.brbrGuests staying at 25 Wildwood can enjoy access to Greenwood Forest’s community amenities, including a playground, seasonal swimming pool, and tennis courts. The home also comes equipped with 4 adult bicycles and backpack beach chairs, making it easy to explore Sea Pines and reach the beach in minutes. With its prime location, contemporary interiors, and thoughtful extras, this home provides everything needed for a memorable Hilton Head Island getaway.brbr• 3 Bedrooms (King, King, Bunk Beds, Twin Rollaway)br• Sleeps 9br• Propane Grillbr• Community Playground, Swimming Pool and Tennis Courtsbr• Access to the Sea Pines Trolley {Seasonal}br• 2 Car Maximum for Parking | *No Parking on the Streetbr• Adult Bikes Provided by South Beach Bicycles/ E Bikes NOT Permitted in Sea Pinesbr• Bath Towels & Bed Linens Provided. Beach Towels NOT Provided.br• 1 Car Pass for the Sea Pines Resort included with your stay. Additional passes may be purchased.br• Pet Friendly with Additional Fee and Restrictions

Bed

Bath

Sleeps

$954.79

/ Nightly

Private Vacation Home

Beach Oriented on the Ocean Golf Course-Large Pool --MAY BE HEATED --NO PETS

Hilton Head Island, South Carolina, United States

An elite, non-smoking property consisting of a large, newly-furnished, five-bedroom, five-bath home and an adjoining two-bedroom, two-bath, guest cottage. This beautiful property is located on the 18th fairway of the prestigious Ocean Golf Course in exclusive Sea Pines Plantation. The property is a short walk to the beach, and near the ' NEW Beach Club.' The beach club has a lifeguard on duty, restrooms, and a restaurant.br brThis luxury home has a gourmet kitchen with Corian counter tops, an over-sized dining room, and large gracious living area. The beautiful master overlooks a private pool and the golf course. The house is newly decorated.brbrThe cottage has a separate living, dining, and kitchen area. A gazebo and furnished patio are ideal for outdoor entertaining.brbrThe property is located near the Marsh Golf Club. Harbor Town is minutes away!!! Property is a few minutes away from the beach club.br Please contact The Bike Doctor for bicycle rentals to obtain discounted prices on weekly bike rentals for our guests. Mention this property to get the discount.brKeywords: House + Cottage

7

Bed

7

Bath

14

Sleeps

$998.22

/ Nightly

Private Vacation Home

Sunset Rentals | Gunnery Lane 4

Hilton Head Island, South Carolina, United States

Welcome to 4 Gunnery Lane, a quintessential Sea Pines home! This beautifully outfitted five-bedroom, five-and-a-half-bathroom home offers the comfort and space you deserve for your next family vacation. With multiple living spaces, bedrooms spanning multiple levels, and a perfectly private pool area, this home will soon become your go-to Hilton Head getaway!brbrAs you enter the home, you’ll find recently refinished hardwood floors and newly painted walls, along with comfortable furnishings in two living areas. The first living area offers a large flat-screen streaming TV with surround sound, two sofas, and two club chairs. The second living area beyond is open to the breakfast area and kitchen. This living area has a large flat-screen streaming TV, a sectional, and two chairs. Both living areas offer views of the expansive pool area. brbrThe breakfast table seats four comfortably, with additional seating for four at the large kitchen island. The kitchen features granite counters, custom cabinets, stainless steel appliances, a gas cooktop, a Keurig coffee maker, and ample cookware! Past the kitchen, you’ll find one of two laundry areas, as well as a formal dining room with seating for ten. brbrTwo of the five bedrooms are on the main level. The spacious main bedroom suite has a king bed, flat-screen TV, dedicated work space, and an expansive bathroom with a large, tiled walk-in shower, jetted tub, and two large vanities. brbrThe second bedroom on the main level has a king bed, a flat-screen TV, and a private bathroom with a walk-in shower. There is also a powder room on the main level for added convenience.brbrUp one set of stairs, you’ll find an area perfect for the kids of the group! There is a mini living area with a flat-screen TV, a loveseat, and a chair, plus a second laundry room with a full-sized washer and dryer for added convenience. This level also features a bedroom with a twin-over-full bunk bed, a separate twin bed, a twin trundle, and a bathroom with a tub/shower combination. brbrUp a half flight of stairs, you’ll find the remaining two bedrooms. One bedroom features a queen bed, flat-screen TV, and a private bathroom with a walk-in shower, while the final bedroom has a king bed, flat-screen TV, and a private bathroom with a tub/shower combination. brbrNot to be undone by the fabulous interior, the exterior of the home is a place of ultimate enjoyment. The pool deck has multiple sitting areas, a gas grill, and a sparkling pool! brbr*The private pool can be heated for an additional fee between Labor Day and Memorial Day. If the outside temperature drops to 55º or below, the pool will not be able to maintain a warmer temperature. If the pool does not reach your desired temperature but is heating, refunds will not be given.brbr*Fireplace is not for guest use.brPet Policy: This home is not pet friendlybrbrbrVehicle Policy: Sea Pines is a gated community requiring car passes for entry. Please specify the number of car passes needed during your stay. Car passes are $17 per pass per week.brbrSea Pines Plantation is Hilton Head Island's original and largest planned resort. While it is currently the home of the 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 baths, 3 golf courses, tennis, a broad range of shops, restaurants and Hilton Head attractions that will please every vacationer.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# 028576

Bed

Bath

Sleeps

$1184.04

/ Nightly

Private Vacation Home

29 Sandcastle Court @ Folly Field Beach | 3D Projector | Pet Friendly | Lagoon Views

Hilton Head Island, South Carolina, United States

Host & Home presents…29 Sandcastle Court! Relax on multiple balconies or in your private outdoor heated pool (and hot tub) with an expansive patio overlooking a serene lagoon. Inside, you will find a 3D projector, PS4, fully equipped kitchen, multiple Smart TVs, and a kid-approved bunk room, making it the ideal getaway for unforgettable vacation memories! This PET-FRIENDLY home features 6 bedrooms and 4 bathrooms, offering the perfect blend of comfort, convenience, and fun for families and groups! All just a ten-minute walk from one of the nicest beaches on the island. Discover the Folly Field Beach area with us!brbrLearn more below!brbr☆☆ HIGHLIGHTS ☆☆brbr✹ Pet Friendly: Bring your furry dog! 1 dog 60lb or less, or 2 dogs where their combined weight does not exceed 100lbs is allowed. There is an additional non-refundable pet fee of $300 for up to 2 dogs. br✹ Modern Comfort: Accommodates up to 27 guests with 6 bedrooms, including a fun Bunk Room for the kids! br✹ Prime Entertainment: Board games, pool toys, ping-pong table, yard games, and a 3D movie projector with movies on DVD!br✹ Fully Stocked Kitchen: Equipped with everything you need to create delicious meals!br✹ Outdoor Oasis: Multiple balconies, a FREE HEATED POOL, deck perfect for lounging, grilling, and gathering, plus an 8 person hot tub!br✹ Location: mid-island in Sandcastles By the Sea, one of Hilton Head's newest gated communities. Plus, several top-tier golf courses, particularly those within Port Royal Plantation and Palmetto Dunesbr✹ Ocean Access: .5 miles to the Folly Field Beach along the beautiful shaded path.br✹ Lagoon Views from every floor!brbr☆☆ LIVING AREA ☆☆ brbrUpon entry you will be greeted with a spacious open-concept living room. Seamlessly connected with kitchen and dining areas it is designed for socializing in style. Aside from the main space, the home offers multiple secondary living areas and balconies. Natural light pours in through floor-to-ceiling windows, offering serene lagoon views over the balcony and private pool outside. brbr✓ Fresh, contemporary furnishings with two plush sofasbr✓ Multiple living areas including a cozy library nook on the top floor, swing bench on a balcony, and 3D projector room for the kids! br✓ Smart TV for movie nights or catching a game!brbr☆☆ OUTDOOR PRIVATE OASIS ☆☆brbrThe cozy and secluded pool deck is perfect for entertaining and chilling, while the BBQ master of the group preps the feast at the grill station. Whether you're enjoying sun-filled days or relaxing evenings, this space is ideal for both. After a day of island adventures, unwind at the pool under the stars as you share stories and plan tomorrow's fun.brbr✓ Private FREE heating pool overlooking the lagoon!br✓ Smart TV right by the pool!br✓ Propane Grillbr✓ 8 Sun Loungers & multiple sofas for outdoor seatingbr✓ Ping Pong Table for some friendly competition!br✓ 8 Person Hot Tub! brbr☆☆ KITCHEN AND DINING ☆☆ brbrStep into the kitchen, ideally situated with serene views of the lagoon, making it a perfect spot for morning coffee or casual dining. The open layout continues into the living room and dining area, ensuring ample space for everyone in your group to enjoy meals and conversations together.brbr✓ Everything necessary to cook and serve basic mealsbr✓ Dripping and Keurig coffee makersbr✓ Farmhouse dining table with seating for 6, plus 4 additional seats at the kitchen island!brbr☆☆ BEDROOMS & BATHROOMS ☆☆brbrThis modern home offers 6 bedrooms and 4.5 bathrooms, each crafted for comfort and relaxation. brbrFloor 2:br✓ Bedroom 1: 1 King suite, en-suite bathroom with walk-in shower, large closet space, decorative arm chair, Smart TVbr✓ Half Bath located near the kitchenbrbrFloor 3:br✓ Bedroom 2: 1 King suite, ensuite with walk-in shower, large closet space, Smart TV br✓ Bedroom 3: 1 King bed, decorative arm chair, Smart TV, access to hallway bathroom with tub/shower combobr✓ Bedroom 4: 1 King bed, access to back balcony, Smart TV, access to hallway bathroom with tub/shower combobr brFloor 4:br✓ Bedroom 5: 3 Twin Beds, Smart TV, Pac-Man cocktail table, access to hallway bathroom with tub/shower combobr✓ Bedroom 6: 3 Double Bunk Beds, 3D movie theater, PS4, access to hallway bathroom with tub/shower combo brbr☆☆ NEARBY ATTRACTIONS☆☆ brbrNearby, you'll find a wealth of attractions to explore, from the beach just stone's throw away to charming shops and world-class dining establishments. Here are some of the best activities and attractions. brbrNEARBY GOLF: Centrally located to several top-tier golf courses, particularly those within Port Royal Plantation and Palmetto Dunes.br✔ Port Royal Golf & Racquet Club: Located very close to Folly Field, this club features three 18-hole courses (Barony Course, Robber's Row Course, Planter's Row Course) br✔ Oyster Reef Golf Clubbr✔ Palmetto Dunes Oceanfront Resort: (Robert Trent Jones Course, George Fazio Course, Arthur Hills Course)brbrDINING AND SHOPPING: Discover a variety of upscale dining and shopping options to enjoy during your stay.br✔ Shelter Cove Towne Centre (3.2 miles)br✔ Coligny Plaza Shopping Center (6.4 miles)br✔ Harbour Town (8.8 miles)brbrFAMILY-FRIENDLY ATTRACTIONS: Explore engaging and premium attractions perfect for all ages nearby.br✔ Adventure Cove Mini Golf & Arcade (.2 miles)br✔ Pirate's Island Adventure Golf (3.2 miles)br✔ Coastal Discovery Museum (4.0 miles)br✔ The Sandbox Children's Museum (6.3 miles)brbr☆☆ OTHER THINGS TO KNOW ☆☆ brbr✓ Beach Towels, Beach Cart, Red Wagon, Kid's Pool Toys, and 4 Chairs are Provided.br✓ 3 Pack & Plays, High Chair, and 2 Cribs are providedbr✓ This house has parking for 4 vehicles in the driveway and 1 in the garage.br✓ The town prohibits parking on the street or unimproved surfaces such as grass or pine straw.br✓ The pool does not have safety equipment. All activities are at your own risk.br✓ Free heated pool & spa. Please let us know beforehand so we can prepare it for your arrival.br✓ Pool Heating Information: This home features an electric pool heater. While it helps maintain a comfortable swimming temperature, the pool temperature will naturally fluctuate with changes in outdoor ambient temperaturesbr✓ PET POLICY: 1 dog 60lb or less, or 2 dogs where their combined weight does not exceed 100lbs is allowed. There is an additional non-refundable pet fee of $300 for up to 2 dogs. br✓ The minimum age requirement for renting this property is 25. br✓ The Town of Hilton Head Island enforces quiet hours between 10:00 PM and 7:00 AM.br✓ STR Permit Number: 073028brbr ☆☆ YOUR STAY - OUR PRIORITY ☆☆brbrAt HOST & HOME we know that you deserve a vacation and we have a perfect place for it. brbrOur carefully curated vacation homes are immaculate, safe, and meticulously maintained, ensuring comfort and quality throughout your stay. Enjoy peace of mind with our 24/7 support, available for assistance and maintenance anytime you need. brbr☆☆ RESERVE YOUR SLICE OF PARADISE ☆☆brbrBook directly with us to enjoy the best value without additional service fees. Elevate your vacation experience with curated activities and a personable approach to make your stay even more memorable.brbr★☆ Book Today & Let Us Take Care Of You In Hilton Head Island! ☆★brbrEager to Read More brHere Are A Few Kind Words From Our Previous Guests:brbr“Our family had a great stay at one of the Host & Home homes. We loved the welcome basket with snacks, wine, and flowers upon our arrival. The kitchen is stocked with everything needed, the space is roomy and modern, and several beach items like towels, toys, chairs, and a wagon made going to the beach easy. We highly recommend it and hope to come back for another visit soon!” – Tanner (Other Location)brbr“We had amazing communication from Host & Home. They were great to deal with & answered our questions very promptly. Everything was organized & very well organized. I would highly recommend them.” –Karen (Other Location)brbr“Really enjoyed our stay!! Condo is clean and well decorated. Love the beach towels available. Love how helpful and friendly Host and Home was from booking to the end. Would book here and with Host and Home again for sure!” –Stephanie (Other Location)

Bed

Bath

Sleeps

$521.15

/ Nightly

Private Vacation Home

Charming 3BR/2Bath Beach Bungalow with Hot Tub!

Hilton Head Island, South Carolina, United States

Featured in the August 2022 issue of Cottages and Bungalows magazine, this beautifully remodeled 3/2 beach bungalow is nestled in a charming neighborhood within walking distance to Folly Field beach. Enjoy a cup of coffee on the back porch in the morning, relax in the 6 person hot tub after an afternoon round of golf on the many courses nearby or sit by the fire pit and watch the stars at night. The Carolina Breeze Bungalow is the quintessential beach cottage and an all-around Happy Place!brbrThis vintage beach babe captures the coastal Carolina vibe with lots of clean bright whites and soothing ocean blues!brbrWith an open area concept, the Carolina Breeze Bungalow is perfect for entertaining or quiet evenings in. The fully-equipped kitchen includes a bar with seating for two, the dining room has room for six and the living area has plenty of space for stretching out and catching a movie on the 55 inch TV.brbrThe master bedroom has an en-suite with walk-in shower and the two guest rooms, one with a queen bed and one with two twin beds, share a tub/shower combination. A sunroom provides a daybed for extra sleeping space with barn doors for privacy.brbrWalk-in laundry room with washer, dryer and storage shelf.brbrThe backyard has a covered porch with ample seating, a 6 person hot tub and fire pit + wood.

3

Bed

2

Bath

7

Sleeps

$432.93

/ Nightly

Private Vacation Home

NEW PET FRIENDLY CONDO IN HARBOR TOWN!

Hilton Head Island, South Carolina, United States

Welcome to your charming coastal hideaway in the heart of the iconic Sea Pines Resort — where live oaks sway in the breeze, bikes outnumber cars, and every turn leads to a postcard-worthy view. Perfectly positioned just steps from the world-famous Harbour Town and a short, scenic bike ride to the Sea Pines Beach Club, this inviting 2-story condo places you right in the center of Hilton Head’s most beloved coastal magic.brbrStep inside and settle into the easy rhythm of Lowcountry living. The first floor welcomes you with a comfortable living room designed for gathering and unwinding, featuring plush seating, a large flat-screen TV, and classic board games for laid-back evenings filled with laughter and friendly competition. Just beyond, sliding glass doors open to your private patio — the perfect spot to sip something cool, grill dinner under the stars, and let the warm island air carry the day away. The adjoining kitchen embraces a timeless, classic style and is fully equipped with everything you need to prepare effortless vacation meals, whether it’s a quick beach breakfast or a relaxed dinner after a day exploring the island. A full-size washer and dryer are also conveniently located here, making longer stays feel just as easy as a weekend escape. The formal dining area comfortably seats six, with plenty of nearby walkable dining options when you’re in the mood to let someone else do the cooking.brbrUpstairs, the home offers a thoughtful layout designed for both connection and privacy. The spacious primary suite features a king-sized bed, flat-screen TV, and two walk-in closets with generous storage for all your vacation essentials. The en-suite bathroom includes a vanity and shower/tub combo for easy, comfortable routines. Down the hall, a serene second bedroom offers a queen-sized bed and convenient access to a full hall bathroom just steps away — perfect for family or friends traveling together.brbrJust beyond your door, the magic of Sea Pines unfolds. Stroll or bike to the charming Harbour Town Yacht Basin, watch the boats drift by beneath the legendary lighthouse, or explore boutique shops, waterfront dining, and live music under the Spanish moss. This is more than a stay — it’s your chance to experience the timeless beauty and relaxed elegance of the Lowcountry from one of its most iconic locations within Sea Pines Resort.brbrPlease note: This is a PET FRIENDLY home! Please let us know if you will be bringing a furry friend with you. There is a $250 non-refundable pet fee for the 1st approved pet and an additional $150 for a 2nd approved pet. There is a 2 dog limit and both pets must weigh 40lbs or lower. Any dogs over 40lbs must be approved by the owner prior to booking. Please let us know if you have any questions! This condo is NON-SMOKING. Once you arrive, you will need to purchase your own car pass at the Sea Pines gate with $20 in cash.

2

Bed

2

Bath

6

Sleeps

$428.83

/ Nightly

Private Vacation Home

20 Forest Dr ~ Sea Pines Gem | Bike to Harbour Town

Hilton Head Island, South Carolina, United States

20 Forest Drive | Short Bike Ride to the Beachbrbr*3 Bedrooms | 3 Bathroomsbr*Sleeps 8br*2 Kings, 1 Queen, 2 Twinsbr*5 TVs | Wi-Fi | Keurig | Gas Grillbr*Comes with Daily Golf and Kids Activitiesbr*$200 Beach Gear Credit Includedbr*Outdoor Showerbr*Community Pool | Tennis Courts | Basketball Court | Playgroundbr*Point Central Keyless Entrybr*Screened-In Porch with TVbr*8 Beach Towels for Guest Usebr*Access to the Sea Pines Trolley (seasonal)br*Monthly Stays Available (October - March)br*3 Car Maximum for Parking | *No Parking on the Street brbrPeaceful Sea Pines Vacation Home in Greenwood ForestbrbrPerfectly situated between Harbour Town and the Atlantic Ocean, this inviting 3-bedroom, 3-bath cottage captures the best of coastal living in the sought-after Greenwood Forest community of Sea Pines.brbrStep inside to an open, airy layout designed for comfort, privacy, and effortless indoor-outdoor living. The updated kitchen features premium appliances and overlooks a spacious great room filled with natural light, stylish furnishings, and a 65 Roku TV—ideal for movie nights or relaxing after a day in the sun. Just beyond, an expansive screened porch provides the perfect setting for morning coffee, evening cocktails, or laid-back gatherings with family and friends. Enjoy dining al fresco or watching the big game on the 50 Roku TV.brbrThe main-floor primary suite offers a king bed, 50 Roku TV, and a private en-suite bathroom complete with a soaking tub and separate shower. A second main-floor guest room includes a queen bed, twin bed, and 32 Smart TV, with easy access to a nearby hall bathroom featuring a walk-in shower. Upstairs, the third guest suite provides additional privacy, offering a king bed, twin bed, 43 Roku TV, and its own private bathroom.brbrStep outside to enjoy the new side deck off the dining area, equipped with a grill for effortless alfresco meals.brbrWith its charming coastal style, peaceful setting, and unbeatable proximity to Sea Pines beaches, golf, and Harbour Town attractions, 20 Forest Drive delivers the perfect blend of comfort, convenience, and Lowcountry charm—your ideal home base for a memorable Hilton Head getaway.brbrNestled within the sought-after Greenwood Forest community, guests will enjoy access to fantastic amenities including a community pool, tennis and basketball courts, a playground, and scenic walking paths. You’ll be just a short stroll from the Shops at Sea Pines Center (utilizing a path from inside the neighborhood), and a quick bike ride to Harbour Town, South Beach Marina, and the iconic Salty Dog Café.brbr*Community Pool is Open Seasonally (April 15 – October 15)br*3 Car Maximum for Parking | *No Parking on the Streetbr*Property May Be Monitored by Exterior Security Cameras

Bed

Bath

Sleeps

$1048.94

/ Nightly

Private Vacation Home

3 Gull Point — Marshfront Luxury in the Heart of South Beach, Sea Pines

Hilton Head Island, South Carolina, United States

Discover your next unforgettable getaway at 3 Gull Point, a stunning five-bedroom, five-and-a-half-bath estate nestled in Sea Pines’ coveted South Beach neighborhood. With sweeping marsh views, elegant finishes, and generous gathering spaces, this home is perfectly made for families or friends seeking both serenity and style. Just an easy 8-minute stroll to South Beach, you’ll have water, sand, and the vibrant Sea Pines community at your fingertips—yet enjoy peaceful marshfront views and privacy the rest of the time.brbrThe large covered porch overlooks the marsh and comes with an outdoor kitchen, built-in grill, TV, relaxing seating, and shuttered walls—perfect for al fresco dining or lounging. Add the pool and spa, and you have your own private oasis. 3 Gull Point is designed to deliver both indulgent relaxation and exciting South Beach moments. Whether you’re sipping coffee overlooking marshland in the morning, grilling with friends at dusk, or taking a short walk to the beach for sunset, this is a place where memories are waiting to be made.brbrTown of Hilton Head STR Permit #76888brbrPROXIMITY TO THE BEACHbr• 8-Minute Walk to the Beachbr• Direct Marsh ViewsbrbrHIGHLIGHTSbr• *Private Heated pool and spa. *This pool has a gas heater and can be heated for an additional fee of $775 - $1275 per week, depending on the season. The spa portion can be heated separately for a charge of $225.00 per week.br• 8 TVsbr• Gas Grill with Propanebr• Outdoor Fireplace Allowed for Guest Usebr• Experience Local Favorites - The Vacation Company has partnered with SERG Take Out Kitchen to make your stay even more convenient! Guests receive a special credit to enjoy delicious, restaurant-quality meals delivered straight to their vacation rental—so you can spend less time cooking and more time relaxing on Hilton Head Island.brbrSEA PINES RESORT FEATURES & AMENITIES [All Sea Pines Resort Features are subject to purchase, seasonality, and availability.]br• Lawton Stablesbr• Golf Courses - Harbour Town Golf Links home to the RBC Heritage Classic. Additional Sea Pines Resort courses include Heron Point by Pete Dye, Atlantic Dunes by Davis Love II, and Sea Pines Country Club [Private]br• Harbour Town Marina - Lighthouse, Shops, Restaurants, Water Activities, Private Boat Chartersbr• South Beach Marina - Shops, Restaurants, Water Activities, Fishing Charters, Dolphin Toursbr• Racquet Clubs - South Beach & Harbour Townbr• Trolley Transportation - Schedule Variesbr• Tower Beach Parking - Property Owners Onlybr• Sea Pines Beach Club Parking - Major Seasonality Restrictionsbr• Ongoing upgrades to enhance the resort include renovations, new construction, and road projects.brbrPROPERTY CONFIGURATIONbr• 5 Bedroomsbr• 5.5 Bathroomsbr• Sleeps up to 12 peoplebr• Parking for a maximum of 5 vehicles. All vehicle parking must be located on improved surfaces, like driveways, and cannot be on grassed or landscaped areas.br• 4783 Square Feetbr• Washer/ Dryerbr• Fully Equipped KitchenbrbrBEDDING BREAKDOWNbr• Bedroom 1- 1 King, 1st floorbr• Bedroom 2 - Bunk Bed (Twin over Twin with Twin Trundle) and Twin Day Bed, Middle Level br• Bedroom 3 - 2 Queen, 2nd floorbr• Bedroom 4 - 1 King, 2nd Floorbr• Bedroom 5 - 1 King, 2nd FloorbrbrPlease Note: Beach renourishment projects are currently underway and will continue through late spring. While work is active at times, the beach remains open for guests to enjoy and access the shoreline daily. We appreciate your understanding as the community works to enhance and preserve our beautiful beaches! brbrPROPERTY REMINDERSbr• No Elevator Accessbr• Pets are not allowedbr• * A total of 4 adult unisex bikes and a beach wagon are included in your amenity fee when booking. Not included with rentals over 21 nights.br• Garage Accessbr• Indoor Fireplace NOT for guest use.br• The Vacation Company's Guest Connect will contain all your check-in information (lock codes, Wi-Fi codes, and other information pertinent to your stay).

5

Bed

5

Bath

12

Sleeps

Vacation Home Rentals By Owner In Hilton Head Island, SC

$1009.1

$419.13

$1171.17

$735.66

$900.79

$1155.0

$550.51

$931.22

$1177.0

$449.93

$422.36

$2393.8

$496.63

$954.79

$998.22

$1184.04

$521.15

$432.93

$428.83

$1048.94

Rent a place that suits your needs

Most popular vacation rentals in Hilton Head Island

$5734.39

$6268.77

$6243.72

$6243.72

$6243.72

$5882.62

$5882.62

$5882.62

$5882.62

$5799.02

Most Popular Cities in South Carolina