Holiday Homes in Hilton Head Island

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Featured Holiday Homes in Hilton Head Island

A few weeks left! Please request extra linens ahead of time if needed..
Hair dryer, towels
A few weeks left! Please request extra linens ahead of time if needed..
9.2 out of 10, Wonderful, (65)
"This property was exactly as presented and met all our needs for a perfect home away from home vacation rental "
A few weeks left! Please request extra linens ahead of time if needed..
Beach. View. Suite. 1 br. 1 ba. Sleeps 5
Outdoor pool
Beach. View. Suite. 1 br. 1 ba. Sleeps 5
9.8 out of 10, Exceptional, (68)
"The condo wasn’t as clean as I expected closets cluttered floors was gritty like sand on them! "
The price is AU$377
includes taxes & fees
22 Sept - 23 Sept
Beach. View. Suite. 1 br. 1 ba. Sleeps 5
Luxury rental - Fall discounted Rates & Min nights - Pool/Spa-75 steps to beach
Outdoor pool, a heated pool
Luxury rental - Fall discounted Rates & Min nights - Pool/Spa-75 steps to beach
10.0 out of 10, Exceptional, (17)
"Had plenty of room for our entire family. House and clean and a good home base for our adventures on HHI."
Luxury rental - Fall discounted Rates & Min nights - Pool/Spa-75 steps to beach
Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown
Smart TV, books
Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown
10.0 out of 10, Exceptional, (17)
"Perfect place in a perfect location to relax and unwind after being at the beach for a few days. The home is cute, clean and comfortable. We enjoyed sitting on the deck watching all the deer. Walked to Harbour Town each evening. We hope to be back!"
The price is AU$582
includes taxes & fees
2 Oct - 3 Oct
Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown
Old Town Bluffton Home + FREE Golf Cart Luxury Home - Sleeps 8
Property grounds
Old Town Bluffton Home + FREE Golf Cart Luxury Home - Sleeps 8
10.0 out of 10, Exceptional, (51)
"This is a wonderful home. Very clean. Really well stocked. Roomy. Host was accessible. Having the golf cart was really a nice perk. Home is close to everything in downtown Bluffton. Highly recommend."
Old Town Bluffton Home + FREE Golf Cart Luxury Home - Sleeps 8
Gorgeous 4 Bedroom / 3.5 Bath house in the heart of Sea Pines / Pet Friendly
View from property
Gorgeous 4 Bedroom / 3.5 Bath house in the heart of Sea Pines / Pet Friendly
2.0 star property
10.0 out of 10, Exceptional, (5)
"This property was absolutely wonderful, Felt like home!! So peaceful and relaxing, Great location, close to everything you would ever need or want. We stay at a lot of VRBOs and We definitely will be returning to this property. 5 star for sure!!"
Gorgeous 4 Bedroom / 3.5 Bath house in the heart of Sea Pines / Pet Friendly
Largest Pool & Decking on The Block! Check out our great rates & reviews!
Property grounds
Largest Pool & Decking on The Block! Check out our great rates & reviews!
9.8 out of 10, Exceptional, (158)
"Our group (friends for 40+ years) takes an annual girls trip. We chose HHI for our trip this year. The house was very clean, spacious yet cozy, and perfect for 8 of us. The pool was big and great. The beach was a very short walk. The kitchen was well stocked. Host reached out beforehand and had all house info to us before it was expected. Five stars all the way ⭐️⭐️⭐️⭐️⭐️."
Largest Pool & Decking on The Block! Check out our great rates & reviews!
Gated Sea Pines home with private pool & large patio - near beaches & golf
Lake
Gated Sea Pines home with private pool & large patio - near beaches & golf
9.4 out of 10, Exceptional, (18)
"Wonderful neighborhood, close proximity to beach, perfect for families."
Gated Sea Pines home with private pool & large patio - near beaches & golf
Marriott's Harbour Club
Villa, 2 Bedrooms, Balcony, Courtyard View | Living area
Marriott's Harbour Club
3.5 star property
9.0 out of 10, Wonderful, (49)
"Check in was great...thank you Mary....who also checked me out! Address is not clearly labeled on the sign out front! Excellent property! Clean, comfortable, very roomy!"
The price is AU$485
includes taxes & fees
2 Oct - 3 Oct
Marriott's Harbour Club
Beautiful single-level home within walking distance of Sea Pines beach and ocean!
Pool
Beautiful single-level home within walking distance of Sea Pines beach and ocean!
10.0 out of 10, Exceptional, (49)
"We enjoyed our short trip to HHI. This house was very clean, beautifully furnished, a great layout for entertaining and the kitchen was nicely stocked with pretty much what ones needs to prepare meals. The neighborhood is quiet and lovely. A quick drive or bike ride to the beach club. Our week was shortened due to Tropical Storm Debby. If you book during hurricane season, get trip insurance! We would definitely stay at this property again. "
Beautiful single-level home within walking distance of Sea Pines beach and ocean!
Coastal Getaway < 1 Mi to Old Town Bluffton!
Fridge, microwave, stovetop, dishwasher
Coastal Getaway < 1 Mi to Old Town Bluffton!
9.6 out of 10, Exceptional, (24)
"The place was very nice, clean and our stay was a very good experience."
Coastal Getaway < 1 Mi to Old Town Bluffton!
Luxurious Two Bedroom Cottage, Enchanting Backyard
A heated pool
Luxurious Two Bedroom Cottage, Enchanting Backyard
10.0 out of 10, Exceptional, (18)
"The house was well-appointed, clean and comfortable. The hosts were responsive to our questions. We greatly enjoyed our stay here with our family and dogs. The location is excellent and the backyard was a nice sanctuary for us. We highly recommend this property."
Luxurious Two Bedroom Cottage, Enchanting Backyard
Forest Beach Townhome 2BR/1.5 Bath Pet Friendly and 1 Block from the Beach
Terrace/patio
Forest Beach Townhome 2BR/1.5 Bath Pet Friendly and 1 Block from the Beach
9.4 out of 10, Exceptional, (17)
"We had so much fun at this rental! It was clean and easy to get to! It was the perfect size and a short walk to the beach or shopping! Definitely would stay here again! "
Forest Beach Townhome 2BR/1.5 Bath Pet Friendly and 1 Block from the Beach
Spacious Upscale Home with Direct Private Access to the Beach and Heated Pool!
Smart TV, ping pong, books
Spacious Upscale Home with Direct Private Access to the Beach and Heated Pool!
9.8 out of 10, Exceptional, (46)
"We had a fabulous week here! Quick walk to the beach and a short drive or bike ride to Sea Pines. Found everything we needed in the house for nights in as well as beach and pool accessories. Already planning our next visit!"
Spacious Upscale Home with Direct Private Access to the Beach and Heated Pool!
PrvtHomeDeerIsl,2Bdrm2Bth,FreeWifi, lrgDeck,HrbrTwn, pets welcome,sm pet fee
Property grounds
PrvtHomeDeerIsl,2Bdrm2Bth,FreeWifi, lrgDeck,HrbrTwn, pets welcome,sm pet fee
9.2 out of 10, Wonderful, (145)
"We love it here. This is one of the most peaceful places we've ever stayed and Carol is a pleasure to work with as always."
PrvtHomeDeerIsl,2Bdrm2Bth,FreeWifi, lrgDeck,HrbrTwn, pets welcome,sm pet fee
Ranch-style home with private pool with spa & golf course view - dog-friendly
Pool
Ranch-style home with private pool with spa & golf course view - dog-friendly
9.2 out of 10, Wonderful, (78)
"Great proximity to leisure trail. Pool was very nice (note that hot tub cannot be heated after Memorial Day, although this is not noted anywhere)"
Ranch-style home with private pool with spa & golf course view - dog-friendly
Private Pool 4 Bedroom 2 Bathroom South Forest Beach Home! 2023 Remodel!
Fridge, microwave, oven, stovetop
Private Pool 4 Bedroom 2 Bathroom South Forest Beach Home! 2023 Remodel!
10.0 out of 10, Exceptional, (74)
"My husband and I stayed here for a long weekend. Booked last minute, but very much enjoyed the house. It was a short walk to the beach and we thoroughly enjoyed the personal pool. House was close to lots of dining options too. Might have to book this house again and bring our kids and grandkids since there is plenty of room!"
Private Pool 4 Bedroom 2 Bathroom South Forest Beach Home! 2023 Remodel!
10% off a week or more, reno 2024, private screened porch, one level
Outdoor pool
10% off a week or more, reno 2024, private screened porch, one level
9.8 out of 10, Exceptional, (39)
"We very much enjoyed our stay at this home. It was clean and the remodeled kitchen and bathrooms were very nice. We grilled out on the back patio for the nights we were there and that was enjoyable. Host was very responsive."
10% off a week or more, reno 2024, private screened porch, one level
91 Dune Ln - Oceanfront Home off of North Forest w/ Pool & Hot Tub, Dog Friendly
Outdoor pool, a heated pool
91 Dune Ln - Oceanfront Home off of North Forest w/ Pool & Hot Tub, Dog Friendly
10.0 out of 10, Exceptional, (129)
"Great location- house was very well stocked (best we have ever experienced. Owner & Manager stopped by twice during the week to confirm everything was OK."
91 Dune Ln - Oceanfront Home off of North Forest w/ Pool & Hot Tub, Dog Friendly
Castle by the Sea 7BR/8BA Luxury Home with Elevator
A heated pool
Castle by the Sea 7BR/8BA Luxury Home with Elevator
10.0 out of 10, Exceptional, (129)
"We arrived at "Castle By The Sea" and found it very clean, well stocked and in good location for visiting the Beach. The home is comfortable and has everything one may need-- dishes, blenders, music speaker, multiple refrigerators, etc. We found Beach Toys, great Beach Towels and a Wagon for transporting all these items for the 5 minute walk to the Beach. We had the opportunity to spend a lot of time in the home since the Tropical Storm paid us a visit on Days 2-5 of our vacation. We spent...
Castle by the Sea 7BR/8BA Luxury Home with Elevator
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Hilton Head Island

Coral Sands Resorts by Palmera
3 outdoor pools, pool umbrellas, pool loungers
Coral Sands Resorts by Palmera
3.5 star property
9.4 out of 10, Exceptional, (592)
"We were not there long just 2 days only to sleep didn't get a chance to use the amenities. Sorry we had more down time."
Coral Sands Resorts by Palmera
14 Laughing Gull - FRIDAY TO FRIDAY BOOKINGS! SEA PINES LUXURY OCEANFRONT!
Pool
14 Laughing Gull - FRIDAY TO FRIDAY BOOKINGS! SEA PINES LUXURY OCEANFRONT!
9.8 out of 10, Exceptional, (12)
"This beach house was a beautiful home. All beds were comfortable bathrooms all worked well. The only issue was the beach access was a very difficult way for anyone to get to the beach because their access was closed and we had to go to the side, which was never stated in the Description it says ocean front beach home !! very difficult to carry things to the beach for the family when you’re paying a price for oceanfront Beach Home !!!you want it to be an oceanfront beach home? That’s why I had to...
14 Laughing Gull - FRIDAY TO FRIDAY BOOKINGS! SEA PINES LUXURY OCEANFRONT!
Marriott's Barony Beach Club
Restaurant
Marriott's Barony Beach Club
3.5 star property
9.6 out of 10, Exceptional, (228)
" Excellent check in and unit very clean and spacious. "
The price is AU$774
includes taxes & fees
6 Oct - 7 Oct
Marriott's Barony Beach Club
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.