Hilton Head Island Vacation Rentals
View Top Destination Searches
Rental Type
Search Radius
Surrounding Areas

Click the pins to select or deselect an area.

Condo Complex
Apply Filter ×

Hilton Head Island Vacation Rentals

  • Guaranteed Bookings with 100% Protection

  • Easy Changes & Cancellation

  • 24/7 Emergency Support

Craig M. VaycayHero Guest

"Booking with VaycayHero was easy. Any questions I had were responded to right away."

Sort By

216 rentals are available

  • This VIP 3 story oceanfront home has been professionally decorated to suit your every need. Here you will enjoy amenities that include a gourmet kitchen, two master suites with jacuzzi tubs, a private 3 hole Putt-Putt plus an oceanfront Billiard Room. This home is ideal for those seeking a truly luxurious vacation.

    First floor includes ocean front living room, TV, ocean front dining Room, kitchen, bedroom 1 has King bed, TV and Private Bath with Jacuzzi tub. Laundry room and private elevator. Second floor bedroom 2 has ocean front master suite with king bed, TV, Sitting Area, Private Balcony, Private Bath with Jacuzzi Tub, bedroom 3 has Queen bed, TV and private bath, bedroom 4 has two full beds, TV and Private Bath.

    Third floor has ocean front billiard room, living area with Queen sleep sofa, bar, private ocean front balcony and half bath, bedroom 5 has two twin beds, TV, private bath, bedroom 6 has full bed, TV and private bath. Laundry room.

    Exterior features private ocean front pool 10' x 26' (can be heated for additional fee) and poolside spa heated for free private beach walk, private 3 Hole Putt Putt and gas grill. Property amenities include free internet, bathroom jetted tub, grill, private elevator, private pool and spa.

    A great large home located right on the beach. We selected this home because of the location and because we neded an elevator for use by my mother-in-law. Check in and check out were very fst and easy. The only problem we had was spotting some very large bugs in the kitchen and master bedroom.

    Hilton Head Island
  • This 3 level oceanfront home features a large oceanfront Living Room with 2 story windows offering magnificent views of the ocean. There is a private dining room, spacious Kitchen with center island & Den plus a Game Room with Ping Pong Table for the children. This home is ideal for a fabulous vacation. Free WiFi.

    First Floor includes Ocean Front Living Room with large flat screen TV, Dining Room, Kitchen, Den with flat screen TV and Half Bath. Bedroom 1 has Ocean Front Bedroom with Two Full beds, TV and Hall Bath. Laundry room.

    Second Floor includes Bedroom 2 has Ocean Front Master Bedroom with King bed, TV, Private Bath & Private Balcony, Bedroom 3 has ocean gront Queen bed, TV, private bath & private balcony. Bedroom 4 has king bed, TV and shared bath, Bedroom 5 has two twin beds, TV, shared bath and multiple balconies.

    Ground Floor includes game room with ping pong table, TV, Queen sleep sofa and full bath. Exterior features private pool 19' x 34' (can be heated for a fee), poolside spa heated for free charcoal grill and private beach walk & outdoor shower.

    Location was wonderful, right on a relatively quiet part of the beach. Access to the beach is shared with the local community, however was immediately behind the trees beside the pool so a little loss of privacy.
    House is large and well laid out,lots of space.
    It was generally clean, however there was quite a lot of fixes needing done. It seems that the house needs an overall update and small repairs done (things like kitchen cabinets, some paintwork)
    leasing company seemed responsive
    rereading the description i think its pretty accurate
    all in all we enjoyed the vacation

    Hilton Head Island
  • Situated in Palmetto Dunes and just 4 houses from the Beach, this exquisite , one of a kind home has never before been on the rental market. Features of this remarkable home include 4 Bedrooms, 4.5 Baths, Two Living Areas, 6 Flat Screen TV's, a Screened Porch & Back Deck overlooking Palmetto Dunes 11 Mile Lagoon System, a Private Pool, Poolside Spa, Outdoor Shower and Private Dock with 2 Person Canoe.

    Guests of 121 Mooring Buoy can look forward to enjoying the "best of both world's" in that they can enjoy the peaceful tranquility of lounging by the Pool and taking in the scenic views of the Lagoon and it's wildlife in addition to enjoying the home's close proximity to the Beach!

    Main Living Room with Flat Screen TV, Dining Room, Fully Equipped Kitchen with Center Island, Breakfast Room, Spacious Den with Flat Screen TV, Half Bath, Master Suite with King bed, Flat Screen TV & Private Bath with Soaking Tub & Shower, Bedroom 2 with King bed, Flat Screen TV & Private Bath with Shower, Bedroom 3 with Two Queen beds, Flat Screen TV & Private Bath with Shower, Bedroom 4 with Queen bed, Flat Screen TV & Private Bath with Shower.

    Exterior features Private Pool (can be heated for a fee), Poolside Spa (can be heated for a fee), Half Bath off Pool Area, Outdoor Shower, Screened Porch overlooking Lagoon, Covered Outdoor Ping Pong Table, Bike rack, Spacious Back Deck with Gas Grill overlooking Lagoon, Private Dock with 2 Person Canoe.

    overall, very satisfied
    screened porch was a special highlight...
    dishwasher may need service or better instructions
    why don't rental properties provide more supplies (paper towels, trash bags, toilet paper, etc.)

    Hilton Head Island
  • This exquisite 3 story Oceanfront Home offers the ultimate Vacation Retreat with Panoramic Oceanfront Views and 5 bedrooms & 5 1/2 baths. This exceptional, one of a kind home has been Professionally Decorated & offers all new furnishings as of June 2012. Guests of 16 Collier Beach can look forward to enjoying the Multiple Living Areas, 7 Flat Screen TV's, an Oceanfront Sunken Bar, Multiple Ocean Front & Ocean View Balconies, Travertine Flooring, Custom Built imported Doors, a Stone Staircase, Private Pool with Poolside Grilling Area and Private Beach Walk. Free WiFi.

    Four generations spent a week together at the beach and despite many storms, we had a great time!

    With small children, the large well appointed kitchen was perfect for preparing our meals and eating in. The flow of this house worked well for us, although having nearly white chairs in the dining area, probably should have been re-thought.

    We didn't get to use the sunken bar on the main level much, but it was great to have a place to stash water bottles and things we might want or need without having to hike up to the kitchen.

    Due to the weather, we didn't get a chance to use the pool much, but it's great that the house shades the pool making it a great place to escape the heat and the sun!

    We were delayed in getting into the house as the cleaning crew must have had their work cut out for them, but it was clean once we got in. The HVAC folks were also in to change filters and the crib rental people came by to pick up the previous renters crib...kind of like grand central station in the beginning. Due to the storms, about a foot of water was blown out of the pool, but a call to the property management got a pool professional readily dispatched to assess and solve the problem and clean debris from the pool.

    We've stayed in several houses on this stretch of beach and we return because we love the area! The beach is less congested, its close to several grocery stores and walking in the area is great!

    Hilton Head
  • This single story, newly renovated home with 4 Bedrooms and 2 Living Areas features a spacious Rear Deck offering elevated Tee-to-Green gallery views of the Par 5, 5th Hole on Harbour Town Golf Links, plus a Private Pool & Spa. Bike easily to the Beach! FREE WIFI is also offered.

    This home has been professionally renovated and decorated inside and out for the 2014 rental season - including a newly constructed and landscaped luxury Pool and Spa.

    Overlooking the 5th Fairway of the Harbour Town Golf Links, this 4 bedroom home features 2 Living Areas with vaulted ceilings and large windows offering expansive views of the golf course. Ideal for families or couples, this home offers 4 Bedrooms and 3 1/2 Baths.

    Exterior features include a huge Back Deck with multiple seating & dining areas offering an elevated panoramic view of the Par 5, 5th hole of Harbour Town Golf Links. Guests of 25 Battery can bike easily to the Beach, Drive to the newly constructed Sea Pines Beach Club or choose to spend the day at the Private Pool.

    Single Story elevated Home. Main Living Room with Vaulted Ceilings & Flat Screen TV & Blu Ray Player, Fully Equipped Kitchen with Center Island & Breakfast Bar, Wet Bar, Dining Area, Carolina Room with Vaulted ceiling overlooking Harbour Town Golf Links, Full Size Laundry Room, Master Bedroom with vaulted ceilings, King bed, HD Flat Screen TV, Vanity Room & Private Bath with Shower & Jacuzzi Tub, Bedroom 2 with vaulted ceilings, King bed, HD Flat Screen TV, Vanity Room & Private Bath, Bedroom 3 with King bed, HD Flat Screen TV & Shared Bath, Bedroom 4 with Twin beds, HD Flat Screen TV & Shared Bath.

    Other exterior features Private Pool measures 18' x 28' & can be heated for a fee, Poolside Spa can be heated for a fee, Spacious Elevated Back Deck with Gas Grill & Multiple Dining & Seating Areas, Bike Rack for up to 8 Bikes.

    Property amenities include Private Pool, Hot Tub, Jetted Tub, Grilling Area, Golf View, DVD or VCR, Multiple TV's.

    We enjoyed the house and property at 25 Battery very much. The house was spacious and came as described, with a nice pool area and a great sun room. The review loses a star because the house was woefully lacking many necessities, such as paper towels, trash bags, kitchen basics such as oil and salt/pepper, pool towels, and so forth - really everything except for a couple rolls of toilet paper for each bathroom. Our coffee machine was broken, but management replaced it the next day. Overall, pleased with our stay.

    Hilton Head
  • This lovely home is just steps from the Beach & features a Professional Kitchen with Stainless Steel Appliances, Gas Range & Granite Countertops. Each bedroom offers a private bath & TV plus there is a Large Flat Screen TV in the living room.

    Ample seating can be found in the Dining Room & guests can enjoy the Screened Porch & Large Back Deck. This home is ideal for Sea Pines beach lovers & those who enjoy the convenience of walking to the S. Beach Marina Village & the Salty Dog. 1 hr/Day free tennis at the South Beach Racquet Club.

    First Floor includes Living Room, Flat Screen TV, Dining Room and Kitchen. Bedroom 1 has Two Queen beds, TV, Private Bath and Bedroom 2 has Two Twin beds, TV, and Private Bath. Laundry Room. Screened Porch. Second Floor Bedroom 3 has Master bedroom with King Bed, TV and Private Bath and Bedroom 4 has King bed and Private Bath.

    Exterior Features Private Pool 12' x 20' (can be heated for additional fee), Gas Grill and Elevated Back Deck.

    The location is perfect. Short walk to the Beach, Salty Dog and South Beach Tennis from the house. Once you get to the beach from house it's at about mile marker 11 on the beach which makes it a short, about 2 mile walk to the Beach Club. The house is laid out nice with four bedrooms and four baths. Tv room is great with large flat screen TV and comfortable leather chairs and couches. Pool was great to take a dip after beaing at the beach or in the evening. Our family & their friends would stay again at #3 Gadwall on our next Sea Pines Vacation. We go every year. Thanks for the good time.

    Hilton Head Island
  • Located within the Palmetto Dunes Resort, this lovely, single level, 4 Bedroom, 4 Bath home is situated on the famous Palmetto Dunes 11 Mile Lagoon System offering guests sweeping views of the Lagoon and the 16th Green of the Fazio Golf Course. Features of this vacation home include a Private Pool, Private Dock, 6 Flat Screen TV's, Gourmet Kitchen with Gas Range and a Spacious Rear Deck overlooking the Private Pool and Lagoon & Golf Course.

    Guests of 15 Promontory Court can look forward to spending their days at their Private Pool or opt to pack a lunch and bike easily to the Beach! The more adventurous guests can book a tee time or rent a Canoe and set out to explore the 11 Mile Lagoon System which winds it's way throughout the Resort, past Ancient Live Oaks draped in Spanish Moss, all while taking in the assortment of wildlife including Snowy Egrets, Blue Herons, Cormorants & an occasional Alligator. This home is ideal for families that enjoy our Island's nature, the sun and the sand!

    Single Level Home features Spacious Living Room with Flat Screen TV, Dining Room, Fully Equipped Kitchen with Gas Range & Flat Screen TV. Master Suite with King bed, Flat Screen TV & Private Bath featuring Double Sinks & Glass Shower. Bedroom 2 with King bed, Flat Screen TV & Private Bath with Glass Shower. Bedroom 3 with Queen bed, Flat Screen TV & Private Bath with Tub/Shower Combo. Bedroom 4 with Twin beds, Flat Screen TV & Private Bath with Tub/Shower Combo. Laundry Room with Full Size Washer & Dryer. Pet Friendly under 15 lbs, Private Pool, Spacious Rear Deck overlooking Pool, Lagoon & Golf Course, Private Dock, Gas Grill with in ground propane tank.

    We had a great time at the home! Everything was clean, the house was roomy and the pool and lagoon were amazing! The only feedback I would have is the blender was very old and didn't work so we were not able to make mixed drinks. Other than that everything was great and sea turtle getaways was very nice and easy to work with.

    Hilton Head Island
  • This charming 4th Row Ocean Home appeals to Sea Pines Beach Lovers of all ages. The Great Room features hardwood flooring and cozy, comfortable furnishings and the large Screened Porch offers relaxing evening breezes and overlooks your Private Pool & Spa. With 3 King beds, & a Queen and Twin bed. This home is ideal for couples and families that enjoy the Beach and all of the wonderful amenities found within the Sea Pines Resort. Free WiFi.

    First floor bedroom 1 has King bed, TV and private bath, bedroom 2 has Queen & twin bed, TV and private bath. Laundry room. Second floor includes living room, TV, dining room and kitchen. bedroom 3 has queen bed, TV and private bath, bedroom 4 has a queen bed, TV and private bath. Exterior Features: Private Pool measures 12' x 24' & Poolside Spa, Gas Grill, Screened Porch, Pool and Spa can be heated for an additional fee.

    Great experience! We love Hilton Head and we love this home. Thank you to Seat Turtle Getaways as well for always being so accommodating to us!

    Hilton Head Island
  • This villa is a rare find since there are only a few 3 bedroom oceanfront villas available at the Shorewood complex. 507 Shorewood is an oceanfront end unit on the 5th floor and offers breathtaking, panoramic oceanfront views.

    The Master bedroom offers a King bed & private bath and the two additional bedrooms each offer 2 Twins beds with private baths. This villa offers a private oceanfront balcony & is an easy walk to Coligny Plaza with over 60 shops & restaurants.

    Single level ocean front villa has ocean front living room, private ocean front balcony, dining room, kitchen, laundry, bedroom 1 has king bed, TV and private bath, bedroom 2 has two twin beds, TV and private bath and bedroom 3 has two twin beds, TV and private bath.

    Exterior features large ocean front pool 66' x 66', poolside hot tub, baby pool and elevator. Property amenities include free internet, baby pool, complex pool and spa.

    We were very happy with this rental with one exception. Everything was nice and clean, very spacious (perfect for six of us) and the views were just beautiful. From the 5-story balcony we could look right onto the beach and out on the ocean, however it was just far enough away that we weren't bothered by any noise. The only down side to this place was that the king bed in the master bedroom was extremely hard. Even though I like a firm mattress, this one was overly firm.

    Hilton Head Island
  • This delightful first floor villa offers fabulous views of the ocean, sound and pool. This villa has been professionally decorated and is sure to please every member of your family. This unique villa features a private staircase which leads from the villa directly down to the pool & beach.

    Single level pool & ocean view villa includes ocean view living room with TV, kitchen, dining room, half bath, bedroom 1 has ocean view master bedroom with king bed, TV & private bath, bedroom 2 has queen bed, shared bath, bedroom 3 has two twin beds and shared bath. Laundry room.

    Exterior features elevator, private deck overlooking pool & ocean and complex beach front pool 20' x 40'.

    We have rented this unit for the last three years. We enjoy our time spent at South Beach, Sea Pines. It has great views and awesome biking. It is great to get away from the north. We find our time here relaxing and very stress free. Working with Sea Turtle Getaways has proved very easy. We enjoy working with them, especially Crane. If we have had a concern it has been quickly resolved.

    Hilton Head Island
  • This lovely villa offers tranquil lagoon and golf course views. The villa features a Living Room & Dining Room plus a spacious Sun Room that runs the entire length of the villa. Ideal for small families or couples looking for a quiet setting. Guests of 104 Fairway Lane enjoy free access to the S. Beach Pool & the Sea Pines Beach Club.

    Single Level Villa includes Living Room, TV, Queen Sleep Sofa, Dining Room, Kitchen, Sun Room and Laundry Room. Bedroom 1 has Queen bed, TV and Private Bath. Bedroom 2 has Two Twin beds and Private Bath. Exterior features Patio with Golf & Lagoon Views, Complex Tennis Court, Free Tennis and Putting Green. Property amenities include Free internet, Complex Pool, Free tennis.

    Very positive. Nicely and recently redone.

    Hilton Head Island
  • Situated on the 5th fairway of the Harbour Town Golf Links, this ground level home has been completely renovated & professionally decorated. The open concept Great Room features a professional kitchen with stainless steel appliances, vaulted ceilings & 3 sitting areas with expansive windows looking out to the pool & 5th Fairway & Green of Harbour Town Golf Links. This home is ideal for golf fans and beach lovers alike.

    Guests of 21 Battery can enjoy all of the amenities that the Sea Pines Resort has to offer including the Sea Pines Beach Club, Harbour Town Marina with it's Candy Striped Lighthouse, The South Beach Marina, home of the Salty Dog Cafe and miles of bike paths that wind their way throughout the Resort. This is a ground level home with no stairs. Free WiFi.

    Ground Floor

    Great Room with 3 Living Areas & large wall mounted Flat Screen TV
    Professional Kitchen
    Bedroom 1 - Master Suite with King bed, Flat Screen TV & Private Bath
    Bedroom 2 - King bed, Flat Screen TV & Private Bath
    Bedroom 3 - Queen bed, Flat Screen TV & Private Bath
    Bedroom 4 - Two Twin beds, Flat Screen TV & Private Bath
    Laundry Room
    Sleep sofa in Living Area

    Exterior Features

    Private Pool 12' x 22' (can be heated for a fee)
    Gas Grill
    Keyless Entry

    Home was clean, spacious and comfortable.

    Hilton Head Island
  • This charming, eclectic beach house is just 1 house from the ocean and is packed with fun. The floor plan includes two living areas, a large dining area, spacious kitchen, deck plus patio. Ideal for Sea Pines Beach Lovers, this home offers free views of the Ocean from the main living room, dining room, kitchen & upper deck. A superb value.

    First floor includes living area, TV, bedroom 1 - Queen bed, hall bath and a laundry Room. Second floor have living Room, TV, dining room, kitchen. Bedroom 2 - King bed, TV, private bath. Bedroom 3 - Double & twin bed, shared bath and bedroom 4 - two twin beds, TV, shared bath.

    Our vacation this year to Spotted Sandpiper was fantastic even though we wish the weather would have cooperated a little more. We loved all of the original artwork the house had to offer. The furnishings were a bit crowded and maybe the house could use a little de-cluttering but honestly at the end of the day, we appreciated the character of the house. Would definitely stay again. Thank you!

    Hilton Head Island
  • This villa offers wireless internet, a separate bedroom with a queen size bed, full size kitchen, living and dining area are combined. Additional bedding for this unit includes a queen size sofa sleeper in the living room and also two bunk beds in the hallway between the bedroom and living room which are ideal for small children. There is a balcony located off the living room which offers a nice oceanfront view.

    Bed Configuration: Bedroom 1: Queen | Hallway: 2 Bunks | Living Room: Queen Sleeper Sofa.

    Overall satisfaction was good. The condo could have used a dining table and a TV in the bedroom. A local tv guide would have been helpful.

    Hilton Head 7.69 miles
  • Wow. Beautiful. Newly renovated, everything brand new. This 4th floor oceanfront villa has a separate bedroom with a king size bed, a full kitchen with granite counter tops and stainless steel appliances, combined oceanfront living room and dining area. Beautiful custom walk-in tile shower. Additional bedding for this condo includes a queen size sofa sleeper in the living room. There is a balcony located directly oceanfront off the living room which offers a panoramic view of the ocean.

    Amenities include Airconditioning, Ceiling Fans, Television, Microwave, Dishwasher, Refrigerator, Oven, Coffee Maker, Balcony and Shared Pool.

    Bed Configuration: Bedroom 1: King | Living Room: Queen Sleeper Sofa.

    One of the best yet! This is a wonderful unit for a couple. Well planned configuration made this villa comfortable and inviting! Very well maintained. View of ocean was fabulous! Access to the beach was easy. Love the Vacation Time staff - they're the best!

    Hilton Head 7.69 miles

See Our Other Locations

See All Locations
View Your Password By signing up, I agree to VaycayHero's Terms of Service & agree to join our mailing list for special offers and travel tips.

Forgot Password?


Our concierge specialist is standing by to help you with your booking.
Call 888-733-2964 .