TOP 30 Best Island vacation rentals in Hilton Head Island, South Carolina

HHI Tide 21 is a family-friendly vacation rental located at 40 Folly Field Road in Hilton Head Island, South Carolina, United States. The owners purchased the property in January 2020 after years of enjoying family vacations on the island with their own children. They have created a welcoming and comfortable space for families to enjoy a beach vacation together. The spacious villa features an open floor plan, coastal decor, and all the amenities needed for a relaxing stay. Children will love the bunk beds, board games, and DVD movies provided, while parents will appreciate the fully equipped kitchen and private balcony. Beach gear, including chairs, umbrellas, and toys, are also provided for guests' convenience.

Overwatch Home Services, LLC is a premier property management company located in Charleston, SC, serving Hilton Head Island and the surrounding areas. Specializing in absentee home watch and vacation rental management, our team ensures that your property is well-maintained and taken care of, even when you're not there. At Overwatch Home Services, we provide detailed reports after each visit to keep you informed about the status and condition of your property. Our experienced team handles maintenance coordination and other necessary services on your behalf, giving you peace of mind knowing that your property is in good hands.

Hilton Head Boat Charters is a premier travel agency located at 43 Jenkins Road on Hilton Head Island in South Carolina, United States. We offer a wide range of boat charters and excursions for visitors looking to explore the beautiful waters surrounding the island. Our experienced captains and crew provide top-notch service and ensure a memorable experience for all guests. Whether you're looking for a relaxing sunset cruise or an exciting fishing trip, Hilton Head Boat Charters has something for everyone. Book your adventure with us today and discover the beauty of Hilton Head from the water.

Island Time Charters Hilton Head Island is a premier tourist attraction and travel agency located at 68 Helmsman Way in Hilton Head Island, South Carolina, United States. This private boat charter company offers quality and comfortable excursions for up to six passengers around the stunning Hilton Head Island. With a variety of exciting charter options ranging from 2 to 7 hours, visitors can customize their experience to suit their preferences. Whether you're looking to explore the local waters, go fishing, or simply relax and soak in the beautiful surroundings, Island Time Charters has something for everyone. All ages are welcome, and the friendly staff will ensure that you have a memorable and enjoyable time on Island Time. Start planning your trip today and get ready for the ultimate charter experience!

Overwatch Home Services, LLC is a premier real estate and travel agency located on Hilton Head Island, South Carolina. Specializing in Absentee Home Watch and Vacation Rental Management, our team at Overwatch Home Services is dedicated to providing top-notch services to homeowners and vacationers alike. Our experienced staff ensures that your property is well-maintained and secure while you are away, offering peace of mind to absentee homeowners. For vacationers, we offer a wide range of rental properties to choose from, all managed with the highest level of professionalism and care. Visit us at 14 Spanish Moss Road and let Overwatch Home Services take care of all your real estate and vacation rental needs on beautiful Hilton Head Island.

Brandon Greenplate of Hilton Head Properties Realty is a reputable real estate agency located in the heart of Hilton Head Island, South Carolina. With a prime location at 12 New Orleans Road, this agency specializes in helping clients buy, sell, and rent properties in the area. Known for their exceptional customer service and in-depth knowledge of the local market, Brandon Greenplate and his team are dedicated to providing personalized and professional real estate services to their clients. Whether you are looking for a vacation home, investment property, or your dream house, you can trust Brandon Greenplate of Hilton Head Properties Realty to help you navigate the real estate market with ease.

eFoil Hilton Head is a premier store located in Hilton Head Island, South Carolina, United States. We specialize in electric hydrofoil boards, also known as eFoils, which provide an exhilarating and eco-friendly way to glide across the water. Our knowledgeable staff is dedicated to helping customers find the perfect eFoil to suit their needs and skill level. Visit us at 6 Bow Circle to experience the thrill of eFoiling for yourself!

Cross Island Bike Rental is a premier bicycle store located at 13 Executive Park Road in Hilton Head Island, South Carolina. We offer a wide selection of high-quality bicycles for rent, perfect for exploring the beautiful island and its scenic surroundings. Whether you're looking for a leisurely ride along the beach or a challenging mountain biking adventure, we have the perfect bike for you. Our knowledgeable staff is dedicated to providing excellent customer service and ensuring that you have a memorable biking experience. Visit us today and start your island adventure with Cross Island Bike Rental.

RE/MAX Island Realty is a premier real estate agency located at 24 New Orleans Road in Hilton Head Island, South Carolina, United States. With a team of experienced and knowledgeable agents, we specialize in helping clients buy, sell, and rent properties on this beautiful island paradise. Whether you're looking for a vacation home, investment property, or permanent residence, our team is dedicated to providing top-notch service and finding the perfect property to meet your needs. Trust RE/MAX Island Realty to help you navigate the real estate market on Hilton Head Island with ease and confidence.

Luxury Homes of Hilton Head is a full-service real estate agency located at 62A New Orleans Road in Hilton Head Island, South Carolina. Specializing in resort and luxury properties, we offer comprehensive services for all your homeownership needs. Our team goes above and beyond to provide exceptional service and expertise to meet our clients' expectations. Whether you're a first-time buyer or a seasoned investor, we are here to guide you through the process of owning a home on Hilton Head Island. We pride ourselves on offering the most up-to-date information about real estate on Hilton Head Island and Bluffton, including details about Homeowner's Associations, Condo Management Regimes, and Property Regulations.

Beachside Getaway - Vacation Rentals is a premier real estate and travel agency located at 1 Corpus Christi Place, Hilton Head Island, South Carolina. Our institution offers a wide range of luxurious vacation rentals situated along the beautiful beaches of Hilton Head Island. Whether you are looking for a cozy beachfront condo or a spacious oceanfront villa, we have the perfect accommodation for your next getaway. Our dedicated team is committed to providing exceptional service and ensuring that your vacation is a memorable and relaxing experience. Book with Beachside Getaway - Vacation Rentals for the ultimate beachside escape in Hilton Head Island.

Hilton Head Properties Realty & Rentals is a premier real estate and travel agency located at 12B New Orleans Road in Hilton Head Island, South Carolina. Specializing in vacation rentals, property sales, and property management services, our experienced team is dedicated to helping clients find their perfect home or vacation rental on this beautiful island. With a wide range of properties to choose from and personalized service, Hilton Head Properties Realty & Rentals is your go-to agency for all your real estate and travel needs in Hilton Head Island. Contact us today to start your journey towards finding your dream property or vacation rental.

Relax Rentals is a premier real estate and travel agency located at 18 Executive Park Road, Hilton Head Island, South Carolina. Specializing in vacation rentals, our experienced team is dedicated to providing top-notch customer service and helping you find the perfect accommodations for your next getaway. Whether you are looking for a beachfront villa, a cozy cottage, or a luxurious estate, Relax Rentals has a wide selection of properties to choose from. Let us help you relax and enjoy your vacation to the fullest. Contact us today to start planning your dream vacation!

Island Explorer Dolphin and Nature Tours in Hilton Head, South Carolina offers personalized eco-tours for small groups looking to get up close and personal with dolphins and the natural beauty of the area. Their custom-built 12-passenger Carolina Skiffs are perfect for families or large groups wanting to explore the waters around Hilton Head Island. In addition to dolphin watching, Island Explorer also offers special expeditions in search of dolphin "strand feeding" during the summer and early fall. Kids of all ages, parents, and grandparents are welcome to join in on the fun and educational experience provided by Island Explorer. Safety and comfort are their top priorities, ensuring that everyone has a memorable and enjoyable time on the water. The Captains at Island Explorer are not only knowledgeable about the area and its wildlife, but they are also friendly and entertaining, making the tour an engaging and informative experience for all. Visit Island Explorer Dolphin and Nature Tours for an unforgettable adventure on Hilton Head Island.

Breeze Bikes is your one-stop shop for all things bicycle and beach gear rentals on Hilton Head Island, South Carolina. Conveniently located at 4D Mathews Court, our store offers a wide selection of high-quality bicycles and beach equipment for rent, perfect for exploring the beautiful island. Whether you're looking to cruise along the scenic bike paths or relax on the sandy shores, we have everything you need to make the most of your time in Hilton Head. Our knowledgeable staff is here to help you find the perfect gear for your adventure, so come visit us at Breeze Bikes today!

Atlantic Bike Rentals is your go-to destination for high quality brand name bikes on Hilton Head Island. Conveniently located at 144C Arrow Road, we offer free delivery, easy booking, and simple upfront pricing for a hassle-free experience. Our bike rentals include free locks and baskets, making it easy for you to explore the beautiful island at your own pace. With the best value in bike rentals on Hilton Head Island, you can trust Atlantic Bike Rentals for a great ride every time. Visit us today and start your adventure on two wheels!

The Vacation Company is a premier real estate and travel agency located at 50 Palmetto Bay Road in Hilton Head Island, South Carolina. Specializing in vacation rentals, they offer a wide range of luxurious properties for visitors to enjoy a relaxing and unforgettable getaway. With a dedicated team of professionals, The Vacation Company strives to provide top-notch customer service and expert guidance to help clients find the perfect rental for their needs. Whether you're seeking a beachfront villa, a cozy cottage, or a spacious family home, The Vacation Company has something for everyone. Book your dream vacation today with The Vacation Company and make memories that will last a lifetime.

The Sea Cloisters on Hilton Head is a premier real estate and travel agency located at 50 Starfish Drive in Hilton Head Island, South Carolina. Our expert team specializes in helping clients find their dream beachfront properties on the stunning shores of Hilton Head. Whether you're looking to buy, sell, or rent a vacation home, our experienced agents are dedicated to providing top-notch service and guidance every step of the way. With a focus on luxury accommodations and unparalleled customer satisfaction, The Sea Cloisters on Hilton Head is your go-to destination for all your real estate and travel needs in this beautiful coastal community.

Hilton Head Long Term Rentals is a reputable real estate agency located at 1000 Main Street in Hilton Head Island, South Carolina. Our agency specializes in providing long-term rental properties for those looking to make Hilton Head their home. With a wide range of rental options available, from cozy condos to spacious family homes, we are dedicated to helping our clients find the perfect place to settle down on this beautiful island. Our experienced team is committed to providing top-notch service and guidance throughout the rental process, ensuring a smooth and stress-free experience for both landlords and tenants. Contact us today to find your ideal long-term rental property in Hilton Head Island.

Luxury Rentals of Hilton Head is a premier real estate and travel agency located at 62C New Orleans Road on the beautiful Hilton Head Island in South Carolina, United States. Specializing in luxury vacation rentals, our team of experienced professionals is dedicated to providing top-notch service and helping clients find the perfect accommodations for their dream getaway. From stunning beachfront properties to elegant villas and cozy cottages, we offer a wide range of options to suit every taste and budget. Whether you're looking for a romantic retreat, a family-friendly vacation, or a relaxing escape with friends, Luxury Rentals of Hilton Head has the perfect rental for you. Contact us today to start planning your unforgettable Hilton Head Island vacation!

Palmera Vacation Club is a premier lodging and travel agency located at 33 Office Park Road in Hilton Head Island, South Carolina, United States. Our institution offers luxurious accommodations and personalized travel services to ensure a memorable vacation experience for our guests. From spacious villas to exclusive amenities, Palmera Vacation Club is dedicated to providing top-notch hospitality and creating unforgettable vacation memories. Book your next getaway with us and discover the beauty of Hilton Head Island in style and comfort.

Hilton Head Ocean View Vacation Rental is a premier real estate and travel agency located at 663 William Hilton Parkway in Hilton Head Island, South Carolina, United States. Our agency specializes in providing luxurious vacation rentals with breathtaking ocean views, allowing guests to experience the beauty of Hilton Head Island in style and comfort. With a wide range of properties to choose from, our experienced team is dedicated to helping you find the perfect accommodation for your dream vacation. Book with us today and create unforgettable memories on the stunning shores of Hilton Head Island.

Hilton Head Speed Boat Tours offers an exciting and unforgettable dolphin tour experience where guests can drive their own two-person skiff boat through the waters of Hilton Head Island, Bluffton, Daufuskie Island, and eco-hotspots. Children 5 and older are welcome as passengers, with no experience necessary for drivers. Each tour is over 2 hours long, allowing guests to witness a variety of wildlife such as jumping stingrays, bald eagles, sea turtles, and baby dolphins. The tour guides are knowledgeable and ensure a safe and thrilling experience for all. Located at Broad Creek Marina with free parking and no gate fees, Hilton Head Speed Boat Tours provides a unique and adventurous way to explore the natural habitat of local dolphins. Whether you choose the skiffs or the traditional style boat, this tour offers a chance to get up close with nature and create unforgettable memories. Highly recommended by past guests, this tour is a must-do activity for visitors to Hilton Head Island.

Kayak Hilton Head is a premier tourist attraction and travel agency located at 18 Simmons Road on Hilton Head Island in South Carolina, United States. Offering a variety of guided kayak tours and rentals, visitors can explore the beautiful waterways and wildlife of the Lowcountry. Whether you're a beginner or experienced paddler, Kayak Hilton Head provides a unique and memorable way to experience the natural beauty of the area. Join us for an unforgettable adventure on the water!

Island Club Resort Sales is a lodging institution located at 85 Folly Field Road in Hilton Head Island, South Carolina, United States. We are passionate about vacations and creating unforgettable memories with your loved ones. As the #1 Independent Resort Management company with over 200 resort destinations across the U.S., Mexico, and the Caribbean, we ensure operational excellence and financial stability for your Association. Join us in Sales & Marketing, Resort Operations, Corporate functions, and more to kickstart your career at Capital Vacations. Discover the value of your Capital Vacations Club Membership and unlock the magic of your next vacation with our Reservation Window tool. We are dedicated to creating memories for all members, owners, and guests while ensuring accessibility compliance at our resorts. Explore new additions in Myrtle Beach and start planning your ultimate 2024 vacation with us. Remember, at Capital Vacations, we want you to 'travel, gather, smile, repeat... year after year'.

Destination Vacation Hilton Head Island is a premier real estate and travel agency located at 7 Executive Park Road in the beautiful Hilton Head Island, South Carolina. Specializing in vacation rentals, property management, and real estate sales, our team of experienced professionals is dedicated to helping clients find their perfect vacation getaway or investment property on this stunning island paradise. Whether you're looking for a luxurious beachfront villa, a cozy cottage in the heart of town, or a spacious vacation home for the whole family, Destination Vacation Hilton Head Island has the expertise and resources to make your dream vacation a reality. Contact us today to start planning your next unforgettable trip to Hilton Head Island.

Beach Properties of Hilton Head is a premier real estate and travel agency located at 64 Arrow Road on Hilton Head Island in South Carolina, United States. Specializing in luxurious beachfront properties, our experienced team of agents are dedicated to helping clients find their dream vacation rental or forever home on this beautiful island paradise. Whether you're looking for a relaxing getaway or a permanent residence by the sea, Beach Properties of Hilton Head is here to make your coastal living dreams a reality. Contact us today to start your journey to the perfect beachfront property.

Disney’s Hilton Head Island Resort is a luxurious lodging option located at 22 Harbourside Lane in Hilton Head Island, South Carolina, United States. Guests can enjoy the thrilling Big Dipper 72,000-gallon heated pool and spa, complete with a wraparound Water Tower Slide for added excitement. For smaller swimmers, the Little Dipper Pool offers a fun and whimsical experience with water-spitting frogs and other playful features. Surrounded by world-class golf courses and stunning coastal beauty, Hilton Head Island is a popular destination for relaxation and recreation. Shelter Cove Harbour, just a short distance from the resort, boasts a marina, fine dining options, and charming boutiques. Nearby attractions include The Arts Center of Coastal Carolina, the Coastal Discovery Museum, and the iconic Harbour Town with its famous lighthouse.

VTrips of Hilton Head is a premier real estate and travel agency located at 578 William Hilton Parkway in Hilton Head Island, South Carolina. Specializing in vacation rentals, property management, and real estate sales, VTrips of Hilton Head offers a wide range of services to help visitors and residents alike make the most of their time on the beautiful island. With a team of experienced professionals dedicated to providing top-notch customer service, VTrips of Hilton Head is your go-to destination for all your vacation and real estate needs in Hilton Head Island.

Weichert Realtors - Coastal Properties | Hilton Head Office is a full-service real estate agency located at 1038 William Hilton Parkway, Hilton Head Island, South Carolina. With five prime real estate offices serving clients in Hilton Head Island, Bluffton, Okatie, Beaufort, South Carolina, and Savannah, Georgia, we offer services for both residential and commercial properties. As the #3 nationally within the Weichert, Realtors Franchises, we have a full administrative staff, Relocation Director, and marketing support team to assist with all real estate needs. Our local reputation and expertise are backed by our membership in Leading Real Estate Companies of the World, a global community of over 565 real estate companies. This ensures that our clients are working with exceptional professionals who can provide connections to buyers and quality real estate companies worldwide. We are also proud members of Luxury Portfolio International, demonstrating our commitment to the luxury market.