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Coastal South Carolina

Hilton Head Vacation Rentals

Hilton Head Vacation Rentals & Beach Rentals with Swimming Pool - 448 Rentals Available.

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Air conditioning (445)
Balcony or terrace (205)
Cot available (1)
DVD player (388)
Dishwasher (424)
Fireplace (10)
Garden (1)
Grill (309)
Heated pool (197)
High Speed Internet (446)
High chair (3)
Hot tub/Jacuzzi (208)
Private indoor pool (51)
Private pool (273)
Private tennis court (1)
Sauna (19)
Swimming pool (448)
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Wi-Fi available (9)

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448 Vacation rentals

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Filters applied: Swimming pool

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1 / 26

Ocean View Villa..75 Yds from beach-from $350/wk

Hilton Head Villa

1 bedroom 1
1 bathroom
Sleeps 6 6
Min stay varies

Beach/lakeside relaxation
Swimming pool
Ask about children

“The condo is in a very nice resort in Hilton Head Island. Also, within that resort it is prime location. There are lots of condos with quite a walk to the beach/pool. This one was ocean view/pool view and just a short walk to both. It was also...”

- Review left on 06/21/2016

$60

Very Good (24 reviews)

from $60 / night

Book

1 / 25

Totally renovated OCEAN VIEW w WIFI and fitness

Hilton Head Apartment

1 bedroom 1
1 bathroom
Sleeps 4 4
3 nights min

Beach/lakeside relaxation
Nearest beach 0.2 mi
Swimming pool

$109

Excellent (11 reviews)

from $109 / night

Book

1 / 18

Gated community condo 200/300 steps to beach

Hilton Head Apartment

2 bedrooms 2
2 bathrooms
Sleeps 6 6
5 nights min

Beach/lakeside relaxation
Nearest beach 0.2 mi
Swimming pool

“Great family rental. Tennis courts, pool close by, bike trails and private beach access. Plenty of room in the condo for the family...”

- Review left on 07/17/2016

$70

Very Good (20 reviews)

from $70 / night

Book

1 / 24

Sun, Sand, Pools, Beach, Tennis, Bicycle Trails

Hilton Head Villa

1 bedroom 1
1 bathroom
Sleeps 4 4
Min stay varies

Beach/lakeside relaxation
Nearest beach 0 mi
Swimming pool

$69

from $69 / night

Book

1 / 24

2nd Row, Tropical 7BR/5BA Pool & Hot Tub

Hilton Head House

7 bedrooms 7
5 bathrooms
Sleeps 14 14
Min stay varies

Swimming pool
Ask about children
Air conditioning

“The house is a great layout for a large family vacation. We had 10 adults and a baby and it was perfectly accommodating. The owners were attentive to any concerns or issues we had upon arrival and were prompt with response - for example, we had one...”

- Review left on 06/03/2015

$550

Very Good (2 reviews)

from $550 / night

Inquire

1 / 22

Sea Pines 3rd Row Beach Walk, 5 Bedrooms

Hilton Head House

5 bedrooms 5
5 bathrooms
Sleeps 15 15
Min stay varies

Beach/lakeside relaxation
Swimming pool
Ask about children

$550

from $550 / night

Book

1 / 15

Steps to Beach & Golf - Newly Renovated Home

Hilton Head House

4 bedrooms 4
3 bathrooms
Sleeps 10 10
Min stay varies

Swimming pool
Child friendly
Air conditioning

$250

from $250 / night

Book

1 / 22

A Great Escape

Hilton Head House

7 bedrooms 7
8 bathrooms
Sleeps 20 20
Min stay varies

Swimming pool
Ask about children
Air conditioning

“Our family of 9 enjoyed a week at this beautiful home as we came together for a family vacation. We have adult children and one grandchild so the rooms were spacious and more than adequate for our needs. The interior is tastefully decorated and the...”

- Review left on 06/17/2016

$500

Excellent (8 reviews)

from $500 / night

Inquire

1 / 23

Sea Pines Central Location! - Walk to Beach/Golf- Private Pool- GOLF VIEW!

Hilton Head Villa

2 bedrooms 2
2 bathrooms
Sleeps 7 7
Min stay varies

Swimming pool
Ask about children
Air conditioning

$208

from $208 / night

Book

1 / 24

Sea Pines Huge Beach Home !

Hilton Head House

7 bedrooms 7
7 bathrooms
Sleeps 20 20
Min stay varies

Swimming pool
Ask about children
Air conditioning

“The house was perfect. One beach block. Heated pool. Sleeps 20. Hot tub. Very clean and well kept. Great family vacation. My daughter graduated from college and we had a family reunion to celebrate. The house was large enough for all to...”

- Review left on 05/18/2016

$400

Excellent (1 reviews)

from $400 / night

Book

1 / 24

Oceanfront on HHI's Best Beach New 5 Bedroom Home

Hilton Head House

5 bedrooms 5
6 bathrooms
Sleeps 12 12
Min stay varies

Beach/lakeside relaxation
Swimming pool
Child friendly

$650

from $650 / night

Book

1 / 28

Beyond Luxury, Oceanfront 8 Bedroom Home w/ Salt Water Pools, Game Rm &

Hilton Head House

8 bedrooms 8
8 bathrooms
Sleeps 20 20
Min stay varies

Beach/lakeside relaxation
Swimming pool
Child friendly

$1655

from $1655 / night

Inquire

1 / 18

216 Barrington OCEANFRONT Booking Winter and Spring NOW!!

Hilton Head Villa

2 bedrooms 2
2 bathrooms
Sleeps 7 7
7 nights min

Beach/lakeside relaxation
Nearest beach 0 mi
Swimming pool

$170

Excellent (1 reviews)

from $170 / night

Book

1 / 12

3 houses, 75yds to beach, great pool NFB

Hilton Head House

6 bedrooms 6
5 bathrooms
Sleeps 16 16
Min stay varies

Swimming pool
Ask about children
Air conditioning

$568

from $568 / night

Inquire

1 / 22

5 Bdrm, Renov, Walk to Beach, Pool, Golf views

Hilton Head House

5 bedrooms 5
4 bathrooms
Sleeps 12 12
5 nights min

Swimming pool
Ask about children
Air conditioning

$571

from $571 / night

Inquire

1 / 24

Lagoon Front, Palmetto Dunes, 5 min walk to beach

Hilton Head Villa

3 bedrooms 3
4 bathrooms
Sleeps 13 13
Min stay varies

Beach/lakeside relaxation
Swimming pool
Ask about children

“What a great place! We were two couples, each with one high school age student. Megan's place was really lovely. The pictures are spot on. It wasn't too big or too small-just right. Lots of space for us all to spread out. We LOVED the deck...”

- Review left on 04/21/2017

$225

Excellent (2 reviews)

from $225 / night

Inquire

1 / 24

Sea Pines, 13 Black Skimmer Rd. Beach View!

Hilton Head House

5 bedrooms 5
6 bathrooms
Sleeps 21 21
Min stay varies

Swimming pool
Child friendly
Air conditioning

$500

Excellent (1 reviews)

from $500 / night

Book

1 / 14

Coligny Villas Forest Beach Condo

Hilton Head Condo

2 bedrooms 2
2 bathrooms
Sleeps 5 5
Min stay varies

Swimming pool
Child friendly
Air conditioning

“Very pleasant and clean unit, furnished with everything we needed for our 2 night stay. Enjoyed being able to walk to the beach and the Coligny Plaza for shopping and eating. Owner was very easy to reach when needed. Would highly recommend renting...”

- Review left on 11/01/2016

$100

Excellent (8 reviews)

from $100 / night

Inquire

1 / 9

Lg Pool, handicap friendly sleeps 14

Hilton Head House

5 bedrooms 5
5 bathrooms
Sleeps 14 14
Min stay varies

Swimming pool
Ask about children
Air conditioning

“Our recent stay at Southwind met our expectations and more. The property had everything a large family needed to make our stay pleasurable. My husband is in a wheelchair and found the island on a whole wheelchair friendly. If only one suggestion...”

- Review left on 07/26/2011

$264

Excellent (2 reviews)

from $264 / night

Inquire

1 / 45

2016 Beach Home w/Elevatr, Heated Pool, Rainshower

Hilton Head House

6 bedrooms 6
4 bathrooms
Sleeps 18 18
Min stay varies

Swimming pool
Ask about children
Air conditioning

$400

from $400 / night

Book

1 / 16

Spacious 3BR/3BA Home with Private Pool in Palmett

Hilton Head House

3 bedrooms 3
3 bathrooms
Sleeps 10 10
Min stay varies

Swimming pool
Child friendly
Air conditioning

“House was awesome, large and comfortable. We had seven guests and could have easily accommodated 3 more. The pool was great, and the community was wonderful. The house is a little over half a mile from the beach which, in this neighborhood, was...”

- Review left on 06/26/2016

$195

Excellent (1 reviews)

from $195 / night

Book

1 / 28

Hilton Head Sea Pines Walk2Beach/book online

Hilton Head House

4 bedrooms 4
4 bathrooms
Sleeps 10 10
Min stay varies

Swimming pool
Child friendly
Air conditioning

“Our trip was wonderful! We had 6 adults, 2 young children, and a dog. Toba and Andy make packing super easy because they provided a high chair, pack n play, toys, and beach towels, chairs, etc. The beach is a short walk and the house is located...”

- Review left on 06/09/2016

$214

Excellent (3 reviews)

from $214 / night

Inquire

1 / 24

Meticulous Oceanside Sea Pines Beach-house! 2nd Row with Ocean Views!

Hilton Head House

4 bedrooms 4
5 bathrooms
Sleeps 16 16
Min stay varies

Swimming pool
Child friendly
Air conditioning

$768

Excellent (1 reviews)

from $768 / night

Book

1 / 14

Walk to Beach - Top Floor - Sleeps 6- Just Updated

Hilton Head Condo

2 bedrooms 2
2 bathrooms
Sleeps 6 6
Min stay varies

Swimming pool
Ask about children
Air conditioning

“My family and I took a trip to Hilton Head for the first time, and we would love to return. I highly recommend this unit as it was super roomy, clean, and had everything you can think of. Indoor/outdoor pools, across the street from the ocean......”

- Review left on 09/23/2015

$100

Very Good (2 reviews)

from $100 / night

Inquire

1 / 43

BRAND NEW Beach House w/Pool, Elevatr Ready In May

Hilton Head House

5 bedrooms 5
4 bathrooms
Sleeps 16 16
Min stay varies

Swimming pool
Child friendly
Air conditioning

$450

from $450 / night

Book

1 / 6

Vacation in This Hilton Head Beach Retreat

Hilton Head Condo

2 bedrooms 2
2 bathrooms
Sleeps 6 6
2 nights min

Beach/lakeside relaxation
Swimming pool
Ask about children

“Spent one week in condo in March. For the price, it is an exceptional value. The description is accurate, owner easy to deal with. Tennis courts, pools and location on the lagoon make it an ideal location. Plenty of enjoyable walks and bike rides...”

- Review left on 03/28/2013

$150

Very Good (3 reviews)

from $150 / night

Inquire

1 / 36

Oceanfront, Sea Pines, 22 Black Skimmer Rd. - Pool

Hilton Head House

6 bedrooms 6
7 bathrooms
Sleeps 12 12
Min stay varies

Beach/lakeside relaxation
Swimming pool
Child friendly

“This was the first time we rented a luxury property, and it was for the occasion of our wedding. Being new, we were unfamiliar with the pricing range as well as the general services that might be available. We found Ted to be very reachable and...”

- Review left on 03/06/2017

$550

Excellent (9 reviews)

from $550 / night

Book

1 / 25

Steps to the Beach, Private Pool/Hot Tub, Poolside Bar, Pet Friendly!!

Hilton Head House

6 bedrooms 6
5 bathrooms
Sleeps 16 16
7 nights min

Swimming pool
Ask about children
Air conditioning

$393

Very Good (20 reviews)

from $393 / night

Inquire

1 / 24

Short Stroll to Beach and Coligny, Private Pool and Game Room

Hilton Head House

5 bedrooms 5
3 bathrooms
Sleeps 10 10
7 nights min

Swimming pool
Ask about children
Air conditioning

$271

Very Good (19 reviews)

from $271 / night

Inquire

1 / 30

Direct Oceanfront Home, Private Pool/Spa

Hilton Head House

5 bedrooms 5
5 bathrooms
Sleeps 12 12
7 nights min

Swimming pool
Ask about children
Air conditioning

$786

from $786 / night

Inquire

1 / 24

Townhouse Located in Shipyard Plantation, Onsite Pool

Hilton Head House

2 bedrooms 2
2 bathrooms
Sleeps 6 6
7 nights min

Swimming pool
Ask about children
Air conditioning

$125

from $125 / night

Inquire

1 / 24

3221 Villamare - Sunny & Bright 2nd Floor Courtyard View Villa. Sleeps 8

Hilton Head Villa

2 bedrooms 2
2 bathrooms
Sleeps 8 8
7 nights min

Swimming pool
Child friendly
Air conditioning

$162

from $162 / night

Inquire

1 / 24

Fabulous Ocean Views from this 2 Bedroom Villa in Shorewood

Hilton Head Villa

2 bedrooms 2
2 bathrooms
Sleeps 6 6
Min stay varies

Swimming pool
Child friendly
Air conditioning

$200

from $200 / night

Inquire

1 / 32

2nd Row Beach Home, Ocean Views, Private Pool/Spa, 5 Minute Walk to Coligny

Hilton Head House

7 bedrooms 7
6 bathrooms
Sleeps 16 16
7 nights min

Swimming pool
Child friendly
Air conditioning

$500

from $500 / night

Inquire

1 / 16

A hop, skip and a jump to the beach and across the street from Coligny Plaza.

Hilton Head House

4 bedrooms 4
4 bathrooms
Sleeps 10 10
7 nights min

Swimming pool
Child friendly
Air conditioning

$325

from $325 / night

Inquire

1 / 29

24 Red Cardinal -2nd row Ocean, Quick Walk to NEW Sea Pines Beach Club

Hilton Head House

4 bedrooms 4
5 bathrooms
Sleeps 10 10
7 nights min

Swimming pool
Child friendly
Air conditioning

$453

Very Good (3 reviews)

from $453 / night

Inquire

1 / 28

1416 South Beach Villa-Fully Refurbished Beachfront Townhouse.

Hilton Head Villa

4 bedrooms 4
3 bathrooms
Sleeps 8 8
7 nights min

Swimming pool
Child friendly
Air conditioning

$301

Excellent (5 reviews)

from $301 / night

Inquire

1 / 20

1103 Villamare-1st floor Oceanfront Villa just steps to the beach!

Hilton Head Villa

2 bedrooms 2
2 bathrooms
Sleeps 8 8
7 nights min

Swimming pool
Child friendly
Air conditioning

$154

from $154 / night

Inquire

1 / 26

52 Gloucester - Zero Entry Pool w/ Spa all at a private home.

Hilton Head House

4 bedrooms 4
3 bathrooms
Sleeps 12 12
7 nights min

Swimming pool
Child friendly
Air conditioning

$284

Excellent (1 reviews)

from $284 / night

Inquire

1 / 25

15 Avocet Street- Pool/Spa, Quick Walk to Beach & Coligny Plaza

Hilton Head House

4 bedrooms 4
3 bathrooms
Sleeps 12 12
7 nights min

Swimming pool
Child friendly
Air conditioning

$341

Very Good (2 reviews)

from $341 / night

Inquire

1 2 3 4 5 6 Next Last

Coastal South Carolina

This is the estimated nightly price based on a weekly stay. Contact the advertiser to confirm the price - it varies depending on when you stay and how long for.

This is the estimated nightly price based on a weekly stay.

This is the total cost of the stay for the dates and number of guests that you entered.

This price is an estimate based on the latest rate information available to us. Contact the advertiser to ask for the exact price, including any additional fees.

Rates for this rental are unknown, please contact the homeowner to confirm the rate.

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