Updating...

Enter dates for more accurate prices

Hilton Head Rentals with Pools

Filter

Hilton Head Rentals with Pools

1,350 vacation rentals

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

Responds fast! avg. 3 minutes

Price per night from

$100

1 / 27

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. 3 minutes

Price per night from

$198

1 / 31

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

Responds fast! avg. 3 minutes

Price per night from

$170

1 / 30

Newly Furnished, Pool, Dog Friendly Home, 3 Bds, 2 Ba 11 Deer Run

Hilton Head house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

Price per night from

$233

1 / 25

Queens Grant 597

Hilton Head villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$119

1 / 21

124 Windward Village - 2 Bedroom Villa -Shipyard Plantation

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 minutes

Price per night from

$100

1 / 31

Harbour Town Home Private Pool, Free Travel Insurance for rest of 2018.

Hilton Head house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

Price per night from

$233

1 / 26

2 bed/2 bath Hilton Head Resort Ocean Villa

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 17 minutes

Price per night from

$200

1 / 24

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. 3 minutes

Price per night from

$185

1 / 30

Renovated 2 Bed/2.5 Bath Pet Friendly Villa, Free Bikes, Tennis, Pool, Beach

Hilton Head house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$83

1 / 24

Bluff Villas 1666

Hilton Head villa

3 bedrooms / 2 bathrooms / sleeps 8

“Perfect Get Away!” The Condo was spacious, clean, and nicely decorated. We had everything we needed for a lovely weekend. This was a girl trip of 5 women. Having towels, linens, soaps and shampoos provided was really nice. The kitchen was well stocked

Price per night from

$151

1 / 21

Surf Court 74 -Updated Forest Beach Townhouse

Hilton Head house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

Price per night from

$120

1 / 28

Courtside 95 - Close to the beach - Large 2 bedroom Townhouse

Hilton Head house

2 bedrooms / 2 bathrooms / sleeps 7

“Good vacation” Very professional and organizer.

Responds fast! avg. 3 minutes

Price per night from

$100

1 / 30

Courtside 94 - Updated Ground Floor 2 bedroom

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

Price per night from

$100

1 / 24

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. 3 minutes

Price per night from

$100

1 / 25

2 bedroom 2 1/2 bath beach oriented condo

Hilton Head apartment

2 bedrooms / 3 bathrooms / sleeps 6

“A1 vacation condo” Absolutely loved our stay! Great location! Loved the balcony and vacinity to the pool.Had everything you need for a wonderful vacation. All you need is to stock the fridge and you're ready to relax. Ready for another stay at Courtsi

Responds fast! avg. 2 hours 21 minutes

Price per night from

$125

1 / 12

462 Plantation Club End Unit, Golf Views, Close to Beach, Pet Friendly

Hilton Head villa

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$100

1 / 23

Courtside 1 - Forest Beach Ground Floor Spacious Condo

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

Price per night from

$100

1 / 25

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. 3 minutes

Price per night from

$189

1 / 31

Ocean Front Resort, Updated and Comfortable -wifi

Hilton Head villa

2 bedrooms / 2 bathrooms / sleeps 6

“Comfortable and affordable” Great place! Really enjoyed everything about it. Wish we could have stayed longer. Definitely somewhere to return to in the future!

Responds fast! avg. 58 minutes

Price per night from

$85

1 / 67

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. 3 minutes

Price per night from

$145

1 / 24

Direct Oceanfront. Just bring your toothbrush!

Hilton Head villa

1 bedroom / 1 bathroom / sleeps 4

“Amazing trip to Hilton Head and perfect location!” My wife and I celebrated our one year anniversary in Hilton Head and stayed Karen's wonderful beachfront condo! The location was perfect and it's less than a two minute walk to the beach. Her place

Responds fast! avg. 1 hour 24 minutes

Price per night from

$150

1 / 12

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

Hilton Head villa

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 minutes

Price per night from

$130

1 / 22

3BR/2BA - Beach Access - Wi-Fi - Pool/Tennis

Hilton Head apartment

3 bedrooms / 2 bathrooms / sleeps 9

“Great Condo, clean and neat.” We are close to the beach. There's plenty to do on the island, even though the weather is a little cold this week. We've had a great time shopping and sight-seeing.

Responds fast! avg. 1 hour 18 minutes

Price per night from

$99

1 / 26

Ocean One 106 - Beach-side 1st Floor Condo

Hilton Head apartment

3 bedrooms / 3 bathrooms / sleeps 10

“great time!” we love staying at ocean one 106! it's always clean and is a spacious condo. with children, it's the perfect location to the pool and beach. the staff is friendly and helpful. looking forward to next year at the same location!

Responds fast! avg. 3 minutes

Price per night from

$140

1 / 29

Tennis master newly renovated 5 min walk to beach

Hilton Head villa

3 bedrooms / 4 bathrooms / sleeps 6

Responds fast! avg. 3 hours 1 minutes

Price per night from

$179

1 / 11

Beautiful Pet Friendly Sea Pines Home, Free Bikes, Pool Access, Walk to Beach

Hilton Head house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

Price per night from

$183

1 / 24

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 th

Responds fast! avg. 3 minutes

Price per night from

$100

1 / 24

Newly Renovated Villa with Partial Ocean View only steps to the beach.

Hilton Head villa

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$145

1 / 17

Hilton Head Island North Shore Place 2 Bdrm 2 Bath Villa *NOV ~ DEC $99/ntly*

Hilton Head condo

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect Location” Super close to beach, restaurants & shopping. Very clean - no complaints! Would definitely stay again.

Responds fast! avg. 29 minutes

Price per night from

$99

1 / 27

Ocean Villa on Hilton Head Island, SC

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

Responds fast! avg. 17 minutes

Price per night from

$150

1 / 21

Stunning Sea Pines Home, Private Pool, Golf Views, Walk to Beach, Free Bikes

Hilton Head house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 minutes

Price per night from

$233

1 / 24

328 Breakers,Newly Remodeled, Beautiful Oceanfront Beach Villa

Hilton Head villa

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 minutes

Price per night from

$121

1 / 22

Forest Beach Villa 405 - 2 Bedroom Spacious Condo

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 minutes

Price per night from

$100

1 / 22

Ocean One 107 - Oceanfront 1st Floor Condo

Hilton Head apartment

2 bedrooms / 2 bathrooms / sleeps 8

“We enjoyed our stay at Ocean One” We choose to stay in condo 107 for location and access to pool and beach. The condo itself could use some maintainance and cleaning beyond the general surface but overall we were satisfied with our stay.

Responds fast! avg. 3 minutes

Price per night from

$145

1 / 25

Surf Court 81 - Forest Beach Townhouse

Hilton Head house

2 bedrooms / 2 bathrooms / sleeps 6

“Lot's of Fun” The condo was really nice. We had 6 people, but there was only room for 4 to sleep. The sofa bed was broken and there were no linens for it either. The 2 twin beds could really use new mattresses. This information is just for the owner's

Responds fast! avg. 3 minutes

Price per night from

$100

1 / 27

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. 3 minutes

Price per night from

$125

1 / 31

48 Deer Run Lane

Hilton Head house

3 bedrooms / 3 bathrooms / sleeps 6

“Dutch” This house is very specious and clean. It lies perfectly at the end of a street and in a quiet area. You only need 7 minutes to walk to the beautiful beach. The bike path is behind the house and goes in all directions.

Price per night from

$215

1 / 25
Viewing 38 of 1,350
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more