50 Best Hilton Head Vacation rentals on Holiday Lettings - Beach rentals

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982 Vacation rentals

10

Vacation villa in Hilton Head

Coastal South Carolina / Hilton Head

1 6 7 nights min

  • 1 bedroom
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
Immaculately clean unit. Tile and carpet throughout. The views are outstanding from the unit's balcony. This Villa is a beautifully decorated one bedroom stay with a queen bed, queen-size sleeper sofa, and built-in bunk beds for 2 children (sleeps 4-6 comfo …see more

from $145 / night

$725 / week

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from $145 / night

(2) Excellent 

24

Vacation apartment with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
new in 2017 Great newly renovated Fully furished Bed 2 bath Villa with indoor and outdoor pools, Jacuzzi, . South forest beach area close to Coligny Plaza . Close to bike paths and restaurants. Guest access WIFI indoor/outdoor Pools Jacuzzi Neighborhood overview Home is …see more

from $85 / night

$575 - $1,020 / week

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Responds fast!
avg. 3 hours 6 minutes

from $85 / night

36

Vacation home with swimming pool, golf nearby in Hilton Head

Coastal South Carolina / Hilton Head

4 13 Min stay varies

  • 4 bedrooms
  • Sleeps 13
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Family members of all ages are going to love North Forest Beach’s sweetheart vacation home - Coastal Tides Beach House. This spacious open plan bungalow has been completely updated inside and out, sleeping up to 13 people and is a rare, wheelchair accessible option, …see more

from $290 / night

$2,030 / week

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from $290 / night

9

Hilton Head Vacation villa rental

Coastal South Carolina / Hilton Head

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Seascape Villas are located on South Forest Beach Drive, just across the street from the gorgeous, wide beach. It is a five-minute walk (about 1000 feet) from our villa to the sand! Best of all, Seascape Villas has its OWN BEACH ACCESS, a private CABANA WITH LOCKED REST …see more

from $99 / night

$693 / week

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Responds fast!
avg. 3 hours 34 minutes

from $99 / night

(1) Excellent 

22

Vacation villa in Hilton Head

Coastal South Carolina / Hilton Head

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Fiddlers Cove Beach & Racquet Club is a 23 acre resort , just a 5 minute shaded walk (or 2 minute bike ride) to Folly Field Beach which is one of the most beautiful beaches on Hilton Head Island. Resort includes two pools, hot tub, several play areas for kids, indoor ra …see more

from $135 / night

$719 / week

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from $135 / night

(38) Excellent 

48

Vacation villa rental

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
We are proud owners of TWO equally beautiful Villas. The other is on the 1st Floor(same building), so if this Calendar shows unavailable please contact us. Our Villas are located right next to the most "Family Oriented" pool and Clubhouse. Both just steps away! Total …see more

from $95 / night

$450 - $990 / week

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Responds fast!
avg. 35 minutes

from $95 / night

(2) Excellent 

14

Vacation villa accommodation

Coastal South Carolina / Hilton Head

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Warm relaxing views await you at 2386 Lighthouse Tennis. This second-floor upper villa has cathedral ceilings and bright living space. The back deck overlooks green grass and a lagoon. The villa has been recently remodeled. Fully-equipped kitchen, with stainless steel a …see more

from $115 / night

$800 - $1,750 / week

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from $115 / night

23

Vacation home in Hilton Head

Coastal South Carolina / Hilton Head

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
Updated, single level, open 3 Bedroom, 2 Bath home in a quiet are of Sea Pines. Master Bedroom with king bed and a private bath and the bedroom opens to a deck that spands 3/4 of the back of the house and overlooks a private backyard that is perfect for grilling and eat …see more

from $175 / night

$1,150 - $1,590 / week

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Responds fast!
avg. 2 hours 5 minutes

from $175 / night

(1) Good 

26

Vacation home in Hilton Head

Coastal South Carolina / Hilton Head

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
With an open floor plan and vaulted ceilings you will feel the true southern charm of this vacation home at the beach. The large screened front porch is perfect for your morning coffee, a game of ping pong, or relaxing in the hammock. And the freedom to sit outside in a …see more

from $227 / night

$1,584 - $3,395 / week

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from $227 / night

26

Vacation home with swimming pool in Hilton Head

Coastal South Carolina / Hilton Head

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This oceanfront, 5-bedroom, 4-bath home with *heated pool and spa is designed for outdoor beach living. This beachside home sleeps up to 12 people. Outside, a few steps from the sun room and pool, is your own private gazebo with grill and outdoor seating on the edge of …see more

from $414 / night

$2,895 - $8,295 / week

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from $414 / night

(1) Very Good 

28

Vacation villa with indoor pool in Hilton Head

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A memorable vacation awaits you at the "Breezin' In Villa at Hilton Head Resort," a quaint 2-bedroom, 2-bathroom villa, which sleeps 4. This unit ensures an unforgettable retreat with its indoor porch, and wonderful resort amenities! Spectacular location within Hilton H …see more

from $90 / night

$500 - $973 / week

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Responds fast!
avg. 9 minutes

from $90 / night

16

Hilton Head Vacation villa rental

Coastal South Carolina / Hilton Head

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Perfect location and just renovated! Within walking distance to many shops, restaurants, entertainment and the BEACH!!! This spacious 3-bedroom, 3-bath condo is all on one floor, on the ground level. It features casual Island decor. The master bedroom has a new king bed …see more

from $104 / night

$725 - $1,250 / week

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from $104 / night

(2) Excellent 

38

Vacation home rental

Coastal South Carolina / Hilton Head

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This one-of-a-kind, 4 bedroom, 4 bathroom, oceanfront home is ideal for a fun beach getaway on Hilton Head Island. Enjoy oceanfront views from almost every room in the home. As you enter the home, you will see a large living area with fireplace and wall-to-wall ocean vi …see more

from $500 / night

$3,500 - $8,950 / week

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from $500 / night

(31) Excellent 

22

Vacation villa with swimming pool, tennis court in Hilton Head

Coastal South Carolina / Hilton Head

1 6 2 nights min

  • 1 bedroom
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Luxurious, one bedroom villa with balcony overlooking the Atlantic Ocean. There are also a two bunk beds just outside the main bedroom, which has a closet with low shelves, great for kids. Villa is fully equipped and 50 yards from pool and beach for fishin …see more

from $65 / night

$500 - $875 / week

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from $65 / night

(1) Excellent 

45

Vacation home rental

Coastal South Carolina / Hilton Head

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
New construction on Hilton Head Island is rare. Plus, this home is Pottery Barn lovers dream! This home has easy access by a short walk or bike ride to the Folly Field Public Beach Park only 0.3 of a mile away. Folly Beach has parking, bathrooms, outdoor showers, a ve …see more

from $600 / night

$5,250 - $5,500 / week

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Responds fast!
avg. 2 hours 6 minutes

from $600 / night

(12) Very Good 

20

Vacation apartment with shared pool, golf nearby in Hilton Head

Coastal South Carolina / Hilton Head

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Bring your family to relax and enjoy the beach with peace of mind. Tastefully decorated with tile floors throughout. Brand new living room furniture with fresh paint throughout (2017). Fully equipped kitchen -- granite countertops, stainless steel appliances -- with …see more

from $125 / night

$750 / week

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from $125 / night

28

Home rental in Hilton Head

Coastal South Carolina / Hilton Head

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
This completely renovated in 2017 home is located inside Sea Pines Plantation at 27 Heritage Road on the 8th Tee of the Harbour Town Golf Course. This is the ideal rental for an active family, or two families that would like to spend time at the beach, riding bikes, pla …see more

from $199 / night

$1,273 - $6,365 / week

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Responds fast!
avg. 3 minutes

from $199 / night

(5) Excellent 

26

Hilton Head Vacation villa rental

Coastal South Carolina / Hilton Head

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to our beautiful & large (1,264 sq) villa on Hilton Head Island, located in prime South Forest Beach area. The villa is less then 1 block to the beach, and just a few minutes' walk or bike ride to the shops at Coligny Plaza. Besides the beach, biking and so …see more

from $122 / night

$854 / week

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Responds fast!
avg. 19 minutes

from $122 / night

35

Vacation home in Hilton Head

Coastal South Carolina / Hilton Head

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Breath-taking Braddock Cove views! Five-minute walk to the sandy beaches or the South Beach Marina Village amenities make this an ideal Hilton Head location for a family vacation! 6 BR, 6 BA Sea Pines home with private *heated pool and hot tub decorated beautifully in …see more

from $480 / night

$2,646 - $6,594 / week

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from $480 / night

(2) Very Good 

19

Vacation condo in Hilton Head

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Newly furnished 2 bedroom 2 bathroom condo. Located on 5th floor overlooking Pool, Garden area and Tennis courts. . Master Bedroom includes queen size bed with large flat screen tv and blu-ray dvd player. Living room has queen size sleeper sofa and large screen tv wi …see more

from $75 / night

$650 - $775 / week

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from $75 / night

(18) Very Good 

33

Vacation villa with golf nearby in Hilton Head

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
WE ARE NOW ACCEPTING RESERVATIONS FOR SUMMER WEEKS. RESERVE EARLY FOR CHOICE WEEKS. ALL INQUIRIES AND CORRESPONDENCE WILL BE ANSWERED PERSONALLY AND PROMPTLY BY JANET JEZEK, THE OWNER OF THE VILLA NOT BY A RENTAL AGENCY THAT CHARGES HIGHER RATES AND EXTRA FEES. NO PET …see more

from $150 / night

$700 - $1,225 / week

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from $150 / night

38

Vacation home with swimming pool in Hilton Head

Coastal South Carolina / Hilton Head

6 18 Min stay varies

  • 6 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Ask about children
Coastal chic, resort-inspired home invites you to slip away from the worries of day-to-day life and create family memories to last a lifetime! This 6 -bedroom, 7 ½ bathroom custom designed home has plenty of indoor and outdoor space for the entire family to relax and e …see more

from $980 / night

$5,235 - $9,295 / week

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from $980 / night

(18) Very Good 

25

Vacation home rental

Coastal South Carolina / Hilton Head

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Just 200 feet from the ocean, this newly-renovated, 5 bedroom home is the perfect place to stay on your next vacation. Located on the corner of Heron Street and Dune Lane in North Forest Beach, this home is just a short walk or bike ride to Coligny Plaza. Enjoy afternoo …see more

from $265 / night

$1,850 - $4,500 / week

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from $265 / night

24

Hilton Head Vacation apartment rental

Coastal South Carolina / Hilton Head

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Relish in a romantic getaway for 2 at this 1-bedroom, 1-bathroom vacation rental condo on the beautiful Hilton Head Island! Follow the boardwalk down to the sandy beach or to the refreshing resort pool. Enjoy quality time with your loved one sipping cocktails on the pri …see more

from $70 / night

$490 - $840 / week

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Responds fast!
avg. 9 minutes

from $70 / night

25

Vacation home in Hilton Head

Coastal South Carolina / Hilton Head

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Delightful 3rd row South Forest Beach vacation home with private *heated pool and spa. 4 bedroom, 3 bath The open floor plan provides a comfortable and spacious house ideal for any family vacation! The living room, dining room, and kitchen are on the 1st floor with easy …see more

from $380 / night

$1,783 - $4,447 / week

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from $380 / night

25

Vacation villa with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This new to the rental market villa, located just a few minutes away from the beach, pools and tennis courts, is a bright, airy 2 BR/2 BA villa located at 547 Queens Grant in Palmetto Dunes. You have found the perfect spot for the family in search of the ideal Hilton He …see more

from $101 / night

$603 - $1,225 / week

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Responds fast!
avg. 3 minutes

from $101 / night

20

Vacation condo in Hilton Head

Coastal South Carolina / Hilton Head

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
504 North Shore Place, North Forest Beach, Hilton Head Island, SC | Rooftop Pool & Spa | TreeTop Ocean Views | Beachside Pool | 2B/2B Sleeps 6 | Top Floor | Penthouse Villa | 2 Bedrooms (King suite & queen suite) 2 Baths + Sleeper Sofa | Guests can enjoy the rooftop po …see more

from $315 / night

$1,575 / week

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from $315 / night

(1) Excellent 

29

Vacation villa with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.48 mi
  • Swimming pool
Enjoy the beauty of Hilton Head Island at a very affordable rate. First class 2 bedroom, 2 full bath condo (non smoking property) that can sleep six. Faces golf course/lagoon, has two pools (one is heated), and LOCATED JUST 2 BLOCKS FROM THE BEACH! Comes fully furnis …see more

from $75 / night

$525 - $845 / week

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from $75 / night

14

Vacation home with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
74 Springwood is a 2nd floor townhouse, newly-redecorated with charming southern beach decor. On first floor of the townhouse, you will find a kitchen which opens up to the dining and living room. Off of the kitchen is the laundry room. The master suite is also located …see more

from $104 / night

$725 - $1,250 / week

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from $104 / night

23

Hilton Head Vacation condo rental

Coastal South Carolina / Hilton Head

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This lovely one bedroom one bathroom oceanview villa is located on the second floor. There is a fully equipped kitchen, dining/living area with a sofa. The master bedroom is furnished with queen size bed. There is two bunk beds perfect for the kids. In addition there is …see more

from $85 / night

$595 / week

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Responds fast!
avg. 1 hour 50 minutes

from $85 / night

(6) Good 

21

Villa rental in Hilton Head with indoor pool

Coastal South Carolina / Hilton Head

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Beautiful ocean views from this pleasant 2 bedroom, 2 bath villa located in building 1 on the third floor at The SeaCrest Resort. This lovely villa has 2 private balconies perfect for enjoying your morning coffee with a view. The kitchen opens to the dining area and se …see more

from $200 / night

$1,110 - $2,822 / week

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from $200 / night

19

Vacation villa in Hilton Head

Coastal South Carolina / Hilton Head

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This wonderfully decorated, fully renovated villa will give you phenomenal views of the Atlantic Ocean! It is located on the 5th floor of a 5 story high rise and is decorated in bright, warm colors evoking images of the sandy beach just outside your window! The living r …see more

from $260 / night

$1,135 - $2,790 / week

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from $260 / night

(1) Very Good 

22

Vacation villa rental

Coastal South Carolina / Hilton Head

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
2 and 1/2 bedroom, 2 bath townhome with beautiful golf course views, right on the 12th Hole of the famous George Fazio golf course. This villa is bright and the location can't be beat if you love golf and tennis. A rear patio right outside the living room faces the gol …see more

from $180 / night

$860 - $1,275 / week

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from $180 / night

19

Vacation villa rental

Coastal South Carolina / Hilton Head

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
Our villa home is perfectly located within the heart of Sea Pines Plantation and less than 100 yards from a lovely stretch of picturesque South Beach and Bradock Cove. It is located only a few steps from the South Beach Village Marina with the famous Salty Dog Cafe and …see more

from $115 / night

$805 / week

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Responds fast!
avg. 2 hours 54 minutes

from $115 / night

24

Vacation villa rental

Coastal South Carolina / Hilton Head

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Enjoy Hilton Head in this completely renovated first-floor, 2-bedroom Springwood Villa. The villa features an open first floor layout with lagoon views and a short walk to the pool. The kitchen has all new appliances and overlooks the dining area and living room. The di …see more

from $79 / night

$550 - $1,100 / week

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from $79 / night

24

Hilton Head Vacation cottage rental

Coastal South Carolina / Hilton Head

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This self-standing two bedroom, two-and-a-half bath home is a great choice for your family vacation. Located at the corner of South Forest Beach Drive and the ocean gate of Sea Pines, you are a three-minute walk from the pristine beach on the private beach path, or a sh …see more

from $125 / night

$725 - $1,400 / week

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from $125 / night

24

Vacation home with swimming pool in Hilton Head

Coastal South Carolina / Hilton Head

5 18 Min stay varies

  • 5 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Stunning 5th-row ocean 5 Bedroom, 5.5 bath treasure nestled on a secluded cul-de-sac. The first thing you will notice is the open concept living area, dining area, and custom kitchen. The living room hosts a large sectional and reading area for one tucked in the corner …see more

from $356 / night

$2,996 - $8,126 / week

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from $356 / night

32

Vacation home with swimming pool in Hilton Head

Coastal South Carolina / Hilton Head

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Welcome to 219 Cordillo Parkway, located in South Forest Beach! The lovely home is an elevated ranch that has been completely remodeled with a beautiful new kitchen and 4 luxurious baths. The freshly-painted home has all new furnishings, flooring, appliances, bedding, …see more

from $222 / night

$1,550 - $3,650 / week

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from $222 / night

(5) Excellent 

Certificate of Excellence

27

Vacation villa with shared pool, golf nearby in Hilton Head

Coastal South Carolina / Hilton Head

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 0.2 mi
  • Swimming pool
  • Child friendly
Stop overpaying for hotel suites with less room, and twice the price! Whether you're planning a special occasion or simply need to unwind after a hectic workweek, make the most of your week and book a stay at Fiddler’s Cove today! This second floor villa, located in b …see more

Certificate of Excellence

from $107 / night

$703 - $895 / week

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Responds fast!
avg. 59 minutes

from $107 / night

(4) Excellent 

24

Villa rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Come unwind in this beautiful 3-bedroom villa in Sea Pines Plantation. Located close to the front gate, Carolina Place has a wonderful community pool and hot tub, as well as lovely lagoon views and onsite tennis. The living room features a flat-screen TV and a sleeper s …see more

from $143 / night

$995 - $1,595 / week

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from $143 / night