St. Helena Island Rentals with Pools

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313 Houses in St. Helena Island with pools

Luxurious Family Getaway on Fripp Island - Golf Views

Saint Helena Island house

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 20

Responds fast! avg. 7 minutes

Match: Swimming pool

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Price per night from

$459

Dataw Island - Bluff Villa 2014

Saint Helena Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

Match: Swimming pool

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Price per night from

$195

Dataw Island - Creekside Escape

Saint Helena Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

Match: Swimming pool

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Price per night from

$195

Harbor Island - Break Time

Saint Helena Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

Match: Swimming pool

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Price per night from

$247

Tranquil Creekside Retreat - Minutes to Beach, Golf, Pools

Saint Helena Island house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 7 minutes

Match: Swimming pool

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Price per night from

$409

Relaxing Coastal Retreat - Harbor Island Bliss

Saint Helena Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 7 minutes

Match: Swimming pool

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Price per night from

$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

Match: Swimming pool

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Price per night from

$115

Tranquil Oceanfront Haven - Perfect for Family Getaways

Saint Helena Island house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 12

Responds fast! avg. 7 minutes

Match: Swimming pool

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Price per night from

$514

Relaxing Golf Retreat - Dataw Island Getaway

Saint Helena Island villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 7 minutes

Match: Swimming pool

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Price per night from

$196

Tranquil Harbor Island Retreat - Steps to Pool & Beach

Saint Helena Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 7 minutes

Match: Swimming pool

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Price per night from

$115

Dataw Island - Birdie Bluff

Saint Helena Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

Match: Swimming pool

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Price per night from

$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

Match: Swimming pool

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Price per night from

$115

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

Saint Helena Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 7 minutes

Match: Swimming pool

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Price per night from

$129

Tranquil Beach Getaway - Ebb Tide Cottage, Family-Friendly

Saint Helena Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 7 minutes

Match: Swimming pool

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Price per night from

$313

Serene Getaway on Dataw Island - Golf & Water Views

Saint Helena Island condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 7 minutes

Match: Swimming pool

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Price per night from

$200

Great rentals within 20 miles that match your search

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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Price per night from

$144

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.

Match: Swimming pool

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Price per night from

$411

2Br 2Ba 1st FL Villa at Brigantine Qtr., Shipyard

Hilton Head villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$180

REMODELED 2 BR 2 BATH UNIT IN ADMIRALS

Hilton Head condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$213

Beautiful 3br 3 Bth Townhome w- FREE Golf each day

Hilton Head townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$287

Airy Couples Getaway with Fantastic Golf Views

Hilton Head villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“A tale of two” The good story: The place is really nice with modern equipment and a great terrace. The location is stunning with great views to the RTJ golf course and good connections to the mainland. The not so good story: We arrived late to a house, which hadn't been cleaned. Towels on the floor, unmade beds etc. It took us a good two hours to get hold of the owner. He managed to get the place cleaned while we ate at a restaurant. All ended well - but it does show a tiny lack of attention from the owner, which isn't very professional. A gas grill without gas adds to this picture. I can only assume the owner is more alert now about these issues, and if so, I have no problem in recommending the place.

Match: Swimming pool

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Price per night from

$230

Match: Swimming pool

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Price per night from

$413

Fripp Island 1 Bedroom Oceanfront Condo! - 2 Free Amenity Cards!!

Fripp Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

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Price per night from

$252

2BR Beach Escape and Condo at Hilton Head

Hilton Head condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great weekend getaway at a great price!” The condo is kept very clean and the host provides lots of great amenities. It is also one of the more affordable options available in the area. We enjoyed our stay and will definitely look to stay here again should we return to the area! Thanks for sharing your beautiful vacation home!!!

Match: Swimming pool

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Price per night from

$224

590 King Cotton Rd - King Cotton #6-Ocean Ridge

Edisto Island villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$184

238 Driftwood Villa - Wyndham Ocean Ridge

Edisto Island villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

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Price per night from

$106

3523 Myrtle St - "Gone Shelling" - Ocean Ri

Edisto Island house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$243

590 King Cotton Rd - King Cotton #3-Ocean Ridge

Edisto Island villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$184

3622 Yacht Club Rd - " Pelican Pointe"

Edisto Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Swimming pool

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Price per night from

$267

2508 Holmes St - "Annabel Lee"

Edisto Island house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

Match: Swimming pool

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Price per night from

$501

31 Whalers Ct - "The Gathering Place"-Ocean Ridge

Edisto Island house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Swimming pool

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Price per night from

$151

518-B Oristo Ridge - "2FAR2FLA" - Ocean Ridge

Edisto Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$117

502 Magnolia Walk Villa -Wyndham Ocean Ridge

Edisto Island villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$151

780 Summerwind Villa - "Going Coastal" Ocean Ridge

Edisto Island villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Awesome!” We had the best vacation ever! The Condo was fabulous and beautiful! Edisto Realty was great to work with. Everything was ready on time and very clean.

Match: Swimming pool

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Price per night from

$157

Spacious 2 BR condo w/ Free Tennis! Palmetto Dunes

Hilton Head villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Roomy” A girlfriend and I stayed in this condo for a week. It was well furnished, clean, but in need of a paint job. Here are some pros and cons... Pros: dual air conditioning controls, great beds, bathroom downstairs, flat screen TV, free bikes, free tennis, nice pool, plenty of dishes, glasses, etc, plenty of room Cons: no ceiling fans, low lights/dark, masterbath shower slow to drain, had to pay for parking pass (+$15) Being of a certain age, we decided that we really need ceiling fans! Who knew! Kevin was very good to deal with, responded promptly, and had an excellent cancellation policy (did not have to use but have an 88 year old father-in-law...). We did not use bikes (rained daily), pool, or tennis since all we wanted to do was sit on beach and shop. However, it was nice to have that option. Would be a good place for people with children.

Match: Swimming pool

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Price per night from

$224

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!!

Match: Swimming pool

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Price per night from

$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.

Match: Swimming pool

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Price per night from

$918

1305 Palmetto Blvd - "Coastal Haven"

Edisto Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$251

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rentals in St. Helena Island

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