St. Helena Island Rentals

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287 Houses

St. Helena Island - Carolina Sunrise

Saint Helena Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

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$315

Luxurious Family Getaway on Fripp Island - Golf Views

Saint Helena Island house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 20

Responds fast! avg. 7 minutes

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$458

Dataw Island - Bluff Villa 2014

Saint Helena Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

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$253

Dataw Island - Creekside Escape

Saint Helena Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

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$192

St. Helena Island - R Anchor House

Saint Helena Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 40 minutes

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$223

Harbor Island - Break Time

Saint Helena Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

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$243

Tranquil Creekside Retreat - Minutes to Beach, Golf, Pools

Saint Helena Island house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 7 minutes

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$425

Stunning Waterfront Escape - Seaside Serenity

Saint Helena Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$155

Relaxing Coastal Retreat - Harbor Island Bliss

Saint Helena Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$115

Coastal Serenity - Ocean View Condo, Steps to Beach, Harbor Island

Saint Helena Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 7 minutes

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$115

Tranquil Oceanfront Haven - Perfect for Family Getaways

Saint Helena Island house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 7 minutes

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$549

Dataw Island - What a View

Saint Helena Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

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$195

Relaxing Golf Retreat - Dataw Island Getaway

Saint Helena Island villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 7 minutes

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$228

Family Paradise on Lands End - Private Dock

Saint Helena Island house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 15

Responds fast! avg. 7 minutes

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$408

Tranquil Harbor Island Retreat - Steps to Pool & Beach

Saint Helena Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 7 minutes

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$115

Dataw Island - Birdie Bluff

Saint Helena Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

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$177

Harbor Island Oasis - Steps to the Beach, Ocean Views

Saint Helena Island condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 7 minutes

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$115

Tranquil Beach Getaway - Ebb Tide Cottage, Family-Friendly

Saint Helena Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$313

Relaxing Beach Retreat - Ocean Views, Steps to Beach & Pool

Saint Helena Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$129

Serene Getaway on Dataw Island - Golf & Water Views

Saint Helena Island condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 7 minutes

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$228

Sea Island Oaks Family Haven - Close to Beach

Saint Helena Island house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 11

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$297

Great rentals within 20 miles that match your search

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$315

Dolphins, Sea Breezes, Miles of Warm Sand

Hilton Head villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$205

Premium Finishes and Amenities

Hilton Head condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

“Nice” Was one of the nicest condos we have rented it was clean and new. The towels were very nice too we will rent again

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$144

306 Barrington Arms -Oceanfront Luxury Villa

Hilton Head villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$228

Burkes Beach House

Hilton Head house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$344

Book Your Summer Stay! Oceanfront Villa!

Hilton Head villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

“Beautiful ocean front getaway” This is a hidden gem as far as resorts. You can't get closer to the ocean for this price. A lil small and dated but perfect for my wife and I on our weekend getaway. I would definitely recommend this place and look forward to staying again!! Gated community,on site eating options and a beach front bar are just a few of the perks. Doesnt get much better for the price!!

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$138

Enjoy the beach and pool at our Edisto Beach vacation home

Edisto Island house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

“relaxing weekend” This home is awesome. The owners made sure we were well informed and the whole experience was just SMOOTH!! Very quiet and relaxing. Spent the weekend and cannot wait to get back there. Thank you for sharing your home. The beach was great, the area is very non commercial which creates a really laid back atmosphere perfect to just kick back.

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$916

5 ⭐️ Discounted! Lovely Historic District Listing

Beaufort house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Excellent experience!” What a wonderful experience! We stayed over the Thanksgiving holiday and we couldn't have felt more at home. In walking distance to all of the shops and a great restaurant we found, Wren. Must try!! Thank you to the Tetley's for making our trip a relaxing, comfortable experience! Highly recommend!

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$198

Hilton Head Island - Spa on Port Royal Sound

Hilton Head apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Quiet relaxation” We absolutely loved our stay! The condo is on the third floor, so there’s great views of the grounds, and a walking path to the ocean and pier. The Plantation was extremely quiet, and the people we did come across were welcoming and friendly. The condo was clean, cozy, stocked with necessary kitchen and even toiletries for the bathroom! That was a pleasant surprise. We spent most of our time sitting on the screened porch listening to the fountains and birds. The owner is very responsive to texts and emails. We definitely recommend this as a vacation spot, and will be back.

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$115

Affordable Villa Hilton Head Palmetto Dunes ***Brand New Kitchen Dec. 2016***

Hilton Head villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$212

Gated community condo 200/300 steps to beach

Hilton Head apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great location and clean unit” The location of this unit is great. The back gate is just outside the unit and the walk to the beach is an easy one. The walk or bike ride to Coligny Beach Park and the shopping plaza was very easy. It's about half a mile. The beach off Ibis St is quiet and not nearly as crowded as the beach at the Shipyard Plantation club house. The club house beach was great because of the restroom facilities and ability to rent chairs and an umbrella, but our family preferred the quieter beach access outside the back gate. Also, the pictures do not do this unit justice. It was much nicer than I expected. The unit was clean and quiet. Our week long stay was great.

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$344

Hilton Head Beach, Golf, Tennis, A Beautiful Villa

Hilton Head villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“GREAT PLACE TO STAY, CLAY COURTS AMAZING, POOLS AND HOT TUB PERFECT BIKING AND BEACH AWESOME.” We Love The Island it is a great place for families found an excellant church to worship at GRACE COMMUNITY. Biked everywhere grilled daily, loved the Clay courts for tennis. Beach was very close by, FACILITIES were decent and very clean. HOPE TO BACK NEXT YEAR.

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$149

Brigantine Villa (Shipyard) w/Private Ocean Access

Hilton Head villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$229

Newly Remodeled Villa/Spectacular Views and Beach Access, Shelter Cove Marina

Hilton Head villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

“Most perfect place to stay” We cannot begin to tell you about the amazing time we had in Hilton Head Island! At first arrival we were so impressed with your Villa and the location. It was more than perfect for our family. It gave us all the flexibility of enjoying kid and adult activities simultaneously. We thoroughly enjoyed the close proximity to the beautiful beach and the accessibility was priceless with two little ones. We enjoyed some of the restaurants in Shelter Cove and especially the live music from your extra large balcony. Your Villa is a gem and we can tell why you fell in love with Hilton Head Island. We fell in love too!

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$516

RELAX or HAVE FUN: 2 bed condo (walk to beach)

Hilton Head apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect Mother's Day Weekend with my son” The location was only two blocks from the beach and has two pools onsite. The condo has everything you need to make your stay comfortable, there was even an infant float sun canopy that we used for our 18 month old grandson. It is also very conveniently located to multiple excellent shops and restaurants.

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$115

“Great value for money.” We really enjoyed our stay at this resort. The villa was clean and comfortable. The owners are very nice to deal with and very helpful. The walk to the beach from on boardwalk is about 6 minutes, not a big deal at all. Overall I would definitely stay here again.

Responds fast! avg. 1 hour 15 minutes

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$343

511 BARRINGTON COURT PALMETTO DUNES HH, SC

Hilton Head condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Fantastic view, incredibly clean, well stocked, comfortable, and a GREAT owner to deal with.” I think the headline says it all, but here's a little more detail. This was absolutely the cleanest condo/hotel/motel/home we've ever stayed in. The owner really, really, gives you a place you can call home for your vacation. It's like you're staying at the home of a good friend who thought of everything for your comfort and enjoyment. If it weren't for Penny, I probably wouldn't write this, because I want to keep this gem to ourselves. But for anyone who works this hard to provide such a wonderful place, well, I had to. How many times have you walked into a condo and see that's it not really dirty, but it's not really clean ? How many times have you run out of toiletries, not even an extra garbage bag left for you, no laundry or dishwasher detergent available ? Every single rental we've had, we had to make a shopping list of all the toiletries we'll need for the week. NOT HERE. Except for the food, obviously, EVERYTHING you could need or want IS PROVIDED. This is a very, very thoughtful owner. With new tv's, appliances, beautiful upgrades, you will not want to leave. The view is absolutely gorgeous. In Palmetto Dunes, the vegetation and trees have really grown, so unless you get an unobstructed view like this 5th floor provides, you'll never see the ocean. At the risk of repeating, the condo smelled great, and was just incredibly clean. I don't know about you, but an unclean rental can just ruin your vacation. The first minute we walked in, we knew we were going to have a great week. Ok, my sales pitch is over, lest I share this secret with everyone. Yes, the 5 star reviews are for real, it's well deserved. Thanks again Penny, and we'll see you on our next trip to the island.

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$410

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