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

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958 Vacation rentals

24

Vacation apartment with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • 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 $135 / night

$945 / week

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from $135 / night

24

Hilton Head Vacation home rental

Coastal South Carolina / Hilton Head

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
**Sandpiper 30** * 3rd Row Ocean Home * 6 Bedrooms * 5 Baths * Private Pool (can be heated for a fee) * 30 Yards to Beach Ideal for large families, this charming 6 bedroom home is located just 30 yards to the beach and offers a Large Living Room with Flat S …see more

from $600 / night

$3000 - $6000 / week

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from $600 / 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 - $700 / week

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from $65 / night

27

Vacation home with swimming pool in Hilton Head

Coastal South Carolina / Hilton Head

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
**Battery Road 25** This single story, newly renovated home with 4 Bedrooms and 2 Living Areas features a spacious Rear Deck offering elevated Tee-to-Green gallery views of the Par 5, 5th Hole on Harbour Town Golf Links, plus a Private Pool & Spa. Bike easily to the …see more

from $390 / night

$1950 - $6000 / week

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from $390 / night

(26) Excellent 

Certificate of Excellence

22

Vacation apartment rental

Coastal South Carolina / Hilton Head

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to your home away from home at The Spa on Port Royal Sound! This condo is nicely furnished and has all the comforts of home. The kitchen is newly updated with stainless steel appliances and quartz countertops and is fully outfitted for prepping, cooking and di …see more

Certificate of Excellence

from $125 / night

$750 - $950 / week

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avg. 23 minutes

from $125 / night

(13) Very Good 

16

Vacation apartment with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

1 6 1 night min

  • 1 bedroom
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
UPDATED! 3/25/14. One bedroom condo with private balcony, full kitchen, ocean and pool view. This recently renovated Sea Side complex features an oceanfront sundeck & swing, two pools, washer and dryer on each floor, elevator access and covered parking with security. …see more

from $80 / night

$450 - $950 / week

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from $80 / night

(4) Excellent 

26

Vacation home in Hilton Head

Coastal South Carolina / Hilton Head

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This charming, completely renovated 3-bedroom, 2.5-bathroom house is the perfect home-away-from-home for a beach vacation, family getaway, golf, tennis, shopping, or ladies book club weekend on Hilton Head Island.  Bridgeport Lane, an intimate neighborhood nestled just …see more

from $200 / night

$1400 - $1960 / week

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avg. 1 hour 0 minutes

from $200 / night

(16) Excellent 

26

Vacation home in Hilton Head

Coastal South Carolina / Hilton Head

6 19 7 nights min

  • 6 bedrooms
  • Sleeps 19
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
14 Heron is a great house for the whole family to enjoy. Located on the corner of North Forest Beach and Heron Street, you are only a few steps to the sand. Enjoy your meals in the gourmet kitchen, featuring a large island and eating bar all open to the dining room and …see more

from $428 / night

$2995 - $6995 / week

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from $428 / night

(18) Excellent 

Certificate of Excellence

20

Hilton Head Vacation apartment rental

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
* Contact owner for special winter rates Stay at our condo for the best of both worlds! Our condo is at an oceanfront resort with a balcony view of a private lagoon with birds, turtles, etc. Recently remodeled two bedroom condo in family friendly Hilton Head Beach and …see more

Certificate of Excellence

from $100 / night

$585 - $985 / week

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from $100 / night

(3) Very Good 

20

Apartment rental in Hilton Head with indoor pool

Coastal South Carolina / Hilton Head

2 8 3 nights min

  • 2 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This 2-bedroom, 2-bathroom condo in Hilton Head Island is perfect for a family vacation. Being part of the Hilton Head Resort Villas you'll enjoy great community amenities, including an indoor pool which is rare! It's also centrally located, so you will be close to all …see more

from $75 / night

$525 - $875 / week

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avg. 1 hour 0 minutes

from $75 / night

29

Vacation home with swimming pool in Hilton Head

Coastal South Carolina / Hilton Head

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
With spectacular ocean and golf course views, 7 Night Harbour is the ideal home for a multi-generational family or two families looking for the perfect place to spend a vacation on Hilton Head. Situated on the signature 10th hole of the Robert Trent Golf Course, this ho …see more

from $545 / night

$3633 - $6650 / week

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avg. 30 minutes

from $545 / night

25

Home rental in Hilton Head with swimming pool

Coastal South Carolina / Hilton Head

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
**Sandpiper 21** Located just 175 yards from the Beach, this beautiful 6 Bedroom home features comfortable furnishings with exceptional Outdoor Living space for family entertaining. Highlights include: 2 Master Suites, 6.5 Private Baths & a Large Private Pool with …see more

from $600 / night

$3000 - $5000 / week

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from $600 / night

33

Vacation villa with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Start unwinding the moment you walk in on the main floor and see the shaded lagoon view through six-foot windows along the walls of the spacious living room that opens to the dining room and kitchen of this INCREDIBLE, 5 BEDROOM, 4 BATHROOM HUNTINGTON VILLA RENTAL. Begi …see more

from $560 / night

$1933 - $4818 / week

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from $560 / night

24

Vacation apartment with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Plan your next escape to Hilton Head Island and stay at this 1-bedroom, 1-bathroom vacation rental condo that comfortably accommodates 6 guests. Enjoy the amazing amenities this resort has to offer, including the largest pool on Hilton Head Island, a poolside bar, tenni …see more

from $85 / night

$595 - $910 / week

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avg. 59 minutes

from $85 / night

(1) Excellent 

23

Vacation apartment accommodation

Coastal South Carolina / Hilton Head

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This Hilton Head condo is primely positioned at one of America’s favorite vacation destinations. You’ll love the southern comfort and small-town charm of this South Carolina getaway. Tucked within one of the island’s resorts, this 2-bedroom condo is an ideal spot for a …see more

from $85 / night

$595 - $840 / week

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avg. 1 hour 0 minutes

from $85 / night

(25) Excellent 

28

Villa accommodation in Hilton Head with shared pool, golf nearby

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
"SEA-esta" is newly renovated 2 bedroom and 2.5 bathroom 2-story end-unit town home in the Ocean Breeze Villas complex located in South Forest Beach on Hilton Head Island, SC. Sleeps 4-6 with a queen size sleeper sofa. It’s just a short 2 block (~500 yards) walk to th …see more

from $125 / night

$565 - $900 / week

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avg. 1 hour 37 minutes

from $125 / night

30

Hilton Head Vacation home rental

Coastal South Carolina / Hilton Head

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Enjoy the ocean views on the veranda of this charming 5 bedroom, 5 bath, oceanfront home that offers direct ocean views from almost every room. Take a swim in your private ocean-side pool with a connecting spa tub. If you prefer to be out of the water & sun, you may enj …see more

from $422 / night

$2950 - $8450 / week

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from $422 / night

(6) Good 

19

Apartment rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

1 6 7 nights min

  • 1 bedroom
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Affordable 1 bedroom Ocean View condo for family or small group. 118 Sea Side Villa is located on South Forest Beach Drive with a beautiful beach that stretches for miles. A 10 minute walk takes you to Coligny Plaza with its many shops, restaurants, bars, coffee shop, …see more

from $85 / night

$590 - $650 / week

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from $85 / night

(4) Excellent 

22

Villa rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Our St. Andrews property is located directly across the street from the Shelter Cover Marina in the middle of the island, making it very accessible to all activities. There is a large pool that overlooks the golf course a few yards from our villa. We are less than two m …see more

from $100 / night

$500 - $800 / week

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Responds fast!
avg. 1 hour 35 minutes

from $100 / night

(1) Good 

6

Hilton Head Vacation apartment rental

Coastal South Carolina / Hilton Head

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Car not necessary
WELCOME TO YOUR DREAM VACATION! Our 2 bedroom, 2 bath condo at Seascape Villas has everything to make your beach getaway one that you'll be reminiscing about for years to come. We know that you and your family will have a fun-filled week at the beach. Enjoy all of the …see more

from $120 / night

$700 - $1000 / week

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avg. 1 hour 58 minutes

from $120 / night

(7) Very Good 

35

Villa rental in Hilton Head

Coastal South Carolina / Hilton Head

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
South Beach Club is located directly on the beach and just steps away from South Beach Village. This is a beautiful, spacious, two bedroom villa with den. You enter a very private, lovely building with a lobby and take the elevator to the first floor. What is so impress …see more

from $325 / night

$1295 - $2234 / week

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from $325 / night

(6) Very Good 

24

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
All dressed up and ready for you! This lovely 2 bedroom, 2 bath, 4th floor villa rental in Palmetto Dunes is OCEANFRONT and loaded with amenities and new features. Decorated in soothing hues of taupe and sky blue, no detail was overlooked. From KABU & BANANA LEAF-WOVEN …see more

from $300 / night

$883 - $2769 / week

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from $300 / night

24

Vacation home with swimming pool in Hilton Head

Coastal South Carolina / Hilton Head

5 15 4 nights min

  • 5 bedrooms
  • Sleeps 15
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Pet-friendly* 5 bedroom, 4 bath Singleton Beach oasis with ample space for group gatherings. Just a 5-minute walk to the beach or take advantage of a free beach shuttle (Memorial Day to Labor Day). The main level of this home features a fully stocked kitchen with everyt …see more

from $1030 / night

$2695 - $5150 / week

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from $1030 / night

(5) Very Good 

24

Hilton Head Vacation home rental

Coastal South Carolina / Hilton Head

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Newly updated beach cottage! This 3 bedroom, 2 bath home is freshly painted and furnished with new linens, furniture and TVs. Located on the corner of North Forest Beach Drive and Osprey Street, this house is the perfect getaway for a family or small group. The house is …see more

from $208 / night

$1450 - $3600 / week

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from $208 / 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

$602 - $1225 / week

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Responds fast!
avg. 30 minutes

from $101 / night

(11) Very Good 

21

Hilton Head Vacation villa rental

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
UPDATED beautiful beach villa! Location: Our villa is located right across the street from the beach front properties but costs about half as much. In addition, we're just a couple of blocks from famous Coligny Plaza which has over 60 shops and restaurants and ki …see more

from $61 / night

$425 - $850 / week

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Responds fast!
avg. 3 hours 36 minutes

from $61 / night

24

Hilton Head Vacation apartment rental

Coastal South Carolina / Hilton Head

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Hilton Head Island is known as the most family-friendly vacation destination in the world, and it’s easy to understand why! With a wide variety of fun outdoor excursions, 24 outstanding golf courses, over 200 stores and shopping outlets, and numerous other attractions, …see more

from $165 / night

$990 - $1155 / week

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avg. 1 hour 0 minutes

from $165 / night

(6) Excellent 

23

Vacation condo with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Come stay at 309 Ocean Dunes Villas on Forest Beach in Hilton Head and enjoy outstanding views from the direct ocean front deck of this beautifully maintained beach condo. Ocean Dunes is close enough to Coligny Circle to enjoy all the action, shops, and restaurants this …see more

from $90 / night

$675 - $1830 / week

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Responds fast!
avg. 3 hours 16 minutes

from $90 / night

(3) Very Good 

25

Vacation home with swimming 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
Relax at this beachside bungalow under the huge Spanish moss-draped oak. Cool off in a private pool with spa, perfect for your family getaway. Just a 3-minute walk to the beach. Hop on the bike path and pedal down to Coligny Plaza in just minutes. The fully-equipped kit …see more

from $279 / night

$1950 - $3450 / week

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from $279 / night

27

Vacation home with swimming pool in Hilton Head

Coastal South Carolina / Hilton Head

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
**Duck Hawk 22** This luxurious Oceanfront Sea Pines Retreat features 5 Bedrooms, 4.5 Baths, Panoramic Oceanfront Views, a Private Oceanfront Pool with Poolside Spa and Spacious Oceanfront Screened Porch. Guests of 22 Duck Hawk can look forward to a truly memorable …see more

from $1200 / night

$6000 - $10000 / week

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from $1200 / night

29

Vacation villa in Hilton Head

Coastal South Carolina / Hilton Head

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Located in the heart of Palmetto Dunes this bright, airy 2 BR/ 2 BA villa located at 3222 Villamare is the perfect spot for the family in search of the ideal Hilton Head vacation. You will find this Villa very well appointed and tastefully decorated with comfortable fur …see more

from $207 / night

$1393 - $2450 / week

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Responds fast!
avg. 30 minutes

from $207 / night

(1) Very Good 

5

Vacation villa in Hilton Head

Coastal South Carolina / Hilton Head

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Situated on the ocean in prestigious Palmetto Dunes in Hilton Head Island, this villa offers a beach lifestyle and great location! Newly renovated interiors with a gorgeous ocean view makes this rental a must. There is on-site heated oceanfront pool and spa as well as …see more

from $214 / night

$1900 / week

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from $214 / 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. PET FRIENDLY- Maximum of two (2) small pets, each weighing 10 pounds or less, and you must ASK for approval of your particular situation …see more

from $150 / night

$750 - $1250 / week

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from $150 / night

(15) Very Good 

28

Vacation villa in Hilton Head

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Enjoy our newly renovated villa at Hilton Head Resort! Granite counter tops, new cabinetry, new flooring, new appliances and new furniture. Enjoy this top floor villa that has just been renovated. It comes with everything you need to make sure your vacation is enjoy …see more

from $94 / night

$548 - $699 / week

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Responds fast!
avg. 3 hours 5 minutes

from $94 / night

(24) Excellent 

38

Hilton Head Vacation home rental

Coastal South Carolina / Hilton Head

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Have your breath taken away! Enjoy spectacular ocean views and breathtaking sunsets from virtually every room in this 7-bedroom, 8-bath, second-row private home located on a quiet street in North Forest Beach. The home is designer furnished and strikingly decorated thro …see more

from $557 / night

$3895 - $9995 / week

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from $557 / night

24

Home rental in Hilton Head with swimming pool

Coastal South Carolina / Hilton Head

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Second row ocean home with private pool on South Forest Beach. This home is a 5 bedroom, 5.5 bathroom home close to Coligny Plaza and Sea Pines Plantation. The home is a short 2-minute walk to the beach. There is a large front porch that wraps around to a screened-in po …see more

from $357 / night

$2495 - $5496 / week

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from $357 / night

(10) Very Good 

60

Vacation apartment 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
BOOK YOUR OFF SEASON VACATION NOW AT THE ONLY GREAT RESORT WITH INDOOR FACILITIES. --- ASK ABOUT OUR SPECIAL OFF SEASON LONG TERM RENTAL (JAN / FEB ONLY) VILLA WITH PRIVATE BALCONY, INDOOR POOL, SAUNA, HOT TUB, & RUNNING TRACK. This is a 2 bedroom 2 bath villa steps f …see more

from $65 / night

$455 / week

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Responds fast!
avg. 45 minutes

from $65 / night

27

Vacation villa with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
8 Hilton Head Beach Villa: Hilton Head Beach Villas is a spacious 30 unit complex spectacularly located on one of the most prized beachfront properties on the Island. This Beautiful 3 Bedroom, 3 Bath Poolside Villa is located in the pretty oceanfront complex- Hilton …see more

from $400 / night

$1213 - $3825 / week

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from $400 / night

24

Hilton Head Vacation home rental

Coastal South Carolina / Hilton Head

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This gorgeous 5-bedroom, 4 1/2-bath home in Sea Pines has everything you need for the perfect family vacation. Located on a quiet street, this home features a large yard with private pool, spa, outdoor dining area, fireplace, grill, and dock! The views from here are bre …see more

from $465 / night

$3250 - $5551 / week

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from $465 / night

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
Beautiful, ocean-oriented, 2 bedroom, 2 bath luxury villa just steps to the beach. Located on the 1st floor you will enjoy people-watching from the outside patio. Both bedrooms have private bathrooms; the master is furnished with king bedding, the 2nd with 2 doubles. …see more

from $259 / night

$863 - $1895 / week

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from $259 / night