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Hilton Head Rentals with Pools

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1,060 beach rentals in Hilton Head with pools

Beautiful Hilton Head Beaches - 3BR/2BA - Beach Access - Wi-Fi - Pool/Tennis

Hilton Head apartment

3 bedrooms / 2 bathrooms / sleeps 9

“Awesome condo, best value for the dollar.” This 3 bedroom condo at Hilton Head Resort was without a doubt the best value for the dollar. Closest building to the beach, and a beautiful pool. Our ladies weekend was wonderful. Thank you Jeff for being so helpful - even when I called with stupid questions!

Responds fast! avg. 1 hour 24 minutes

Match: Swimming pool

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Price per night from

$228

Courtside 117 - Forest Beach Townhouse Recently Updated

Hilton Head house

2 bedrooms / 2 bathrooms / sleeps 6

“Great family time” I love it very nice :) cant wait to booked my next vacacion.

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$129

Ocean Villa on Hilton Head Island, SC - Steps from the beach and pool.

Hilton Head apartment

1 bedroom / 1 bathroom / sleeps 4

“Great Accommodations and Location!” This was a wonderful vacation rental for our little family. The condo was perfectly decorated, very clean, and a quick walk to the beach. Irene (owner) was quick to answer all of our questions. I can't say enough about how kind Irene is. We enjoyed our days at the beach and swimming in the pool, then visited nearby restaurants for dinner. We had a wonderful time!

Responds fast! avg. 22 minutes

Match: Swimming pool

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Price per night from

$152

Ocean One 419 -Updated Lovely Oceanfront 4th Floor Condo

Hilton Head apartment

3 bedrooms / 3 bathrooms / sleeps 10

“Just what we needed to relax for Labor day” Wonderful place, wonderful beach and pooltime! Seashore Vacations was wonderful to deal with too.

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$358

Hilton Head Resort Villa 2225

Hilton Head villa

2 bedrooms / 2 bathrooms / sleeps 5

“Good overall” We loved Hilton Head! It was very quiet while we were there and the water was perfect for children (3 & 1). The indoor pools perfect for getting out of the sun for a bit and never crowded! The walk to the beach is doable but not recommended for a pregnant woman with 2 small kids! We couldn’t figure out how to have the ceiling fan in bedroom on without the light and messaged to find out but didn’t get a response until after we had checked out. We also couldn’t get water to stay in the bathtub to give our small kids a bath which was VERY aggravating but we managed. Having to pay 1.50 to wash a load of towels was not to great either (was a quarter short to dry them for 1.50 so they hung dry) when been used to having in room washer/dryer On the plus side it seemed to be the cleanest place I have stayed in awhile. All staff that we encountered was very friendly, nice, and helpful.

Responds fast! avg. 29 minutes

Match: Swimming pool

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Price per night from

$99

Courtside 94 - Updated Ground Floor 2 bedroom

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$136

Ocean One 402 - Beachside 4th Floor Condo

Hilton Head apartment

4 bedrooms / 3 bathrooms / sleeps 9

“Second Time Around” This was our 2nd stay at Ocean One 402. I am sorry to say this year the condo was the total opposite of last year in regards to cleanliness. We vacuumed as soon as we arrived and the furniture was thick with dust in every room. The bedspreads were very soiled, and carpet in living room was in dire need of scrubbing. Last year the place was immaculate.

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$335

Carolina Club #440 is part of Spinnaker Resorts

Hilton Head townhouse

3 bedrooms / 4 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$297

Shorewood 431 - Oceanview 4th Floor

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Luibrand Stay @ 431 Shorewood” The whole kitchen was renovated which was very nice. However the two bathrooms need renovation badly and the carpet needs to be cleaned. I love Shorewood

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$202

Ocean Gate 9 - Forest Beach Townhouse

Hilton Head house

2 bedrooms / 2 bathrooms / sleeps 6

“Nice stay” Quiet Villa close to beach. Nice pool and tennis court with little use. Villa amenities adequate. Furnishings fair, beds xtra-firm, but did the job. Could use some paint as of 8-11-13. But nothing disappointing. I will stay here again as the villa, the quiet area, close proximity to the beach, and the pool/tennis courts are a draw.

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$111

328 Breakers,Newly Remodeled, Beautiful Oceanfront Beach Villa

Hilton Head villa

1 bedroom / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$104

3 Quincy, Private Pool, Sleeps 6

Hilton Head house

3 bedrooms / 2 bathrooms / sleeps 6

“Perfect, Great House , Location, a True "Home Away from Home"” Great location, easy access to all that HHI has to offer, All the amenities were great, excellent Wi-Fi, really comfortable beds, so easy to use everything the owner had everything we needed in his welcome pack and was always very responsive to any questions we had prior to arrival and while we was there. I would Highly recommend this rental, we took our dog with us and she loved it also

Responds fast! avg. 38 minutes

Match: Swimming pool

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Price per night from

$376

26 Gunnery Lane, Free Bikes,Tennis, Dog Friendly

Hilton Head house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$128

2 bed/2 bath Hilton Head Resort Ocean Villa-Best Location in Hilton Head Resort

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 22 minutes

Match: Swimming pool

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Price per night from

$192

Modern and Freah Hilton Head Condo - Walking Distance to the Beach

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Very nice place.” All the amenities that you could ever need at the beach - nice indoor pool, outdoor pool, hot tub, sauna, exercise room and short walk to the beach. We loved Coco's and great food. Lois

Match: Swimming pool

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Price per night from

$144

Ocean One 202 - Beachside 2nd Floor Condo

Hilton Head apartment

4 bedrooms / 4 bathrooms / sleeps 10

“Ocean One 202” Nice unit. Owner just needs to open the wallet a little and get a new TV in the main living room. Can't beat Ocean One's location.

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$392

Surf Court 16 - Forest Beach 1st Floor Flat

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 6

“I Loved This Condo!” I have stayed at Surf Court a few times. This condo was my favorite by far! Wonderful week at the beach!!

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$134

362 Sea Side Villa 1 Bedroom- steps from the beach

Hilton Head villa

1 bedroom / 1 bathroom / sleeps 4

“worth it” Located within easy reach (two miles) of Sea Pines where rest of family was staying and about a half mile from amenities at Coligny Circle on nice stretch of beach. Condo was small, but toward front of complex with good beach view from balcony. Well-maintained. Minor miff: wished that glass of sliding door was not so streaky. Had difficulty upon night arrival finding my way to condo. No place to park outside gate; key fob thingamajig hard to find behind tree once I finally found condo and got keys out of box and then walked back to car. Bicycles also hard to locate.

Responds fast! avg. 2 hours 13 minutes

Match: Swimming pool

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Price per night from

$174

Spacious 3 bedroom Villa Walking Distance to Beach

Hilton Head villa

3 bedrooms / 4 bathrooms / sleeps 8

“Absolutely wonderful” Beautiful location, super close to the beach. Everything was so nice and very clean when we arrived! Would absolutely stay here again!

Responds fast! avg. 49 minutes

Match: Swimming pool

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Price per night from

$150

Lake Forest 3304 - Sea Pines One Level Condo

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 6

“wonderful! all the 4s should be 5 tablet trouble” We loved the island and the property. I would only note that the cleaning crew unloaded a trash bag of ours from the outside trashcan and left it in the street. We saw them do this as we checked out, but had to return our bikes. I would think the neighbors wouldnt be happy with their carelessness.

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$129

Beachwalk 122 - Beautiful 1st Floor Flat

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Positive experience” Love the place - been here twice before and will likely try to get the same place next year. One thought though is that the sofa furniture is becoming a little uncomfortable with upholstery and pillows becoming mis-shapen. We felt sitting at the ends of the sofa they were sagging toward the middle - minor point really.

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$147

Short Walk to the Beach, Pet Friendly Shipyard Villa

Hilton Head house

2 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$150

Tennis Master 1101 Private and Recently Updated, 5 Minute Walk to the Beach

Hilton Head villa

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 2 hours 35 minutes

Match: Swimming pool

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Price per night from

$178

Ocean One 315 - Oceanfront 3rd Floor Condo

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Best condo yet.....” We always return to Ocean One due to its location and our wonderful experiences with the property. This unit has been our favorite so far. We will definitely return and hopefully be able to rent this unit again.

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$343

124 Windward Village - 2 Bedroom Villa -Shipyard Plantation

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$145

Beautiful home in Sea Pines with private pool bikes and tennis! Walk to Beach

Hilton Head house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$199

2 Bedroom Townhouse, Springwood Villas, Short Walk to Beach

Hilton Head house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$150

17 Dune - "The Cottage" - Oceanfront 7 Bedroom, North Forest Beach, Free Pool He

Hilton Head house

7 bedrooms / 7 bathrooms / sleeps 16

Match: Swimming pool

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Price per night from

$995

Ocean One 319 - Oceanfront 3rd Floor Condo

Hilton Head apartment

3 bedrooms / 3 bathrooms / sleeps 7

“Great location” Positive but expensive. Many units rented for significantly less for the same week.

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$329

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!!!

Responds fast! avg. 2 hours 29 minutes

Match: Swimming pool

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Price per night from

$173

Ocean One 409 - Oceanfront 4th Floor Condo

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 7

“Exceeded Our Expectations” We rented this condo for 5 nights starting on Labor Day. My husband and I arrived at the rental office early (1:15 pm) and we were able to move into the condo 30 minutes later. Seashore Vacations was great to work with. They were professional and very customer oriented and accommodating. The condo was very clean and had a remodeled kitchen and new living room furniture. The Master Bedroom overlooks the ocean and pool with its own balcony and 2 chairs. The main balcony is accessed through the Living Room and had seating for 6. We loved the ocean and pool views from both. The bathrooms looked like they too had been recently updated. They supplied enough paper products and soaps that the only thing we had to purchase was regular dish washing detergent. There was a ton of storage space throughout the condo. They even had chairs and floats for the ocean or pool. We did purchase an umbrella at the nearby Piggly Wiggly to use on the beach. The kitchen was well stocked with everything we needed. We liked the layout of the condo with the Kitchen and Living Room on one side and both bedrooms and bathrooms on the other side. The Master Bedroom had a huge closet and more hangers than we needed. The pool and ocean were both a short walk - the access to both were just off the elevator. The pool was right below our condo and the beach right beyond the pool. The beach was clean and big enough that we were never crowded. There were showers between the ocean and pool area to wash off sand. The pool was cleaned and treated every morning and was delightful! Housekeeping did a great job and everything was very clean and well-maintained. The only minor issue was the closet door in the foyer which was difficult to open and close (maybe because of all the sand - this was where the beach chairs and floats were stored). But this was really no big deal. We would definitely return to Ocean One and stay at Unit 409.

Responds fast! avg. 11 minutes

Match: Swimming pool

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Price per night from

$245

95,Seapines,pool,golf disc,wifi,bikes,pet ok,tennis

Hilton Head villa

2 bedrooms / 2 bathrooms / sleeps 5

Match: Swimming pool

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Price per night from

$137

New to Market, 312 Breakers. Sleeps 4, Free Bikes, Pool

Hilton Head villa

1 bedroom / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$112

3 BR Nearest to Beach on Lagoon-Golf View-2 Decks

Hilton Head villa

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 36 minutes

Match: Swimming pool

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Price per night from

$269

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

$121

319 Breakers, Fully Remodeled! Beautiful Oceanfront, Pool, Beach, Free Bikes

Hilton Head villa

1 bedroom / 1 bathroom / sleeps 4

Match: Swimming pool

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Price per night from

$104

1701 Bluff Villas / Walk to Beach and Salty Dog / 2nd Row Ocean

Hilton Head condo

1 bedroom / 1 bathroom / sleeps 4

“Heaven on the Bluffs” We had the most wonderful week at 1701. When we walked in the condo was spotless, all immenities we could have needed, Very comfortable and inviting and to top it off a beautiful view! Tom was so accommodating in every way. Each time I contacted him with a question he responded very promptly and with an genuine willingness to help. The experience was memorable and we hope to return.

Responds fast! avg. 3 hours 39 minutes

Match: Swimming pool

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Price per night from

$127

Hilton Head Island, Fiddler's Cove - Pool/Beach, Balcony, Secured WiFi, HDTV's

Hilton Head villa

2 bedrooms / 2 bathrooms / sleeps 6

“Quiet and comfortable condo for Hilton Head stay.” The condo was in very good condition with all the necessary amenities. It's a quiet development that close to the beach. One thing that I didn't anticipate is that Hilton Head is different to other resort areas in that instead of being dominated by buildings it's dominated by beautiful trees. Sometimes it's hard to find things as you drive along because there are few signs and lots of trees. We didn't bike but we walked a lot on the network of bike paths.

Responds fast! avg. 21 minutes

Match: Swimming pool

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Price per night from

$98

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