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

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1,021 Vacation rentals

(4) Very Good 

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 $90 / night

$600 - $1,020 / week

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avg. 2 hours 32 minutes

from $90 / 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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avg. 2 hours 18 minutes

from $290 / night

(15) Very Good 

28

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
  • 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 $93 / night

$558 - $737 / week

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from $93 / night

(2) Very Good 

12

Vacation apartment with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Earlier Check In and Later Check Out than most villa's!!FREE Internet service provided.At the Hilton Head Island Beach and Tennis Resort enjoy the gorgeous ocean view and sunrise on Hilton Head Island while relaxing in our completely renovated one bedroom ocean villa. T …see more

from $150 / night

$950 / week

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from $150 / 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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avg. 2 hours 28 minutes

from $99 / night

(31) Very Good 

22

Apartment rental in Hilton Head with indoor pool, golf nearby

Coastal South Carolina / Hilton Head

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool
Newly furnished 2 BR, 2 BA with Queen Sleeper, comfortably sleeps 6. This unit has a screened in patio with a view of the lagoon and partial view of Port Royal Sound. The master bedroom has a very comfortable queen size bed with its own flat screen tv. The second bedro …see more

from $100 / night

$700 / week

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avg. 45 minutes

from $100 / night

23

Hilton Head Vacation condo rental

Coastal South Carolina / Hilton Head

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Air conditioning
Comfortable, Convenient and Reasonable. Bring your bike and park your car! The unit can sleep up to 4. New queen size foam bed + new queen sleeper sofa. Free wifi & cable and a 39'' Samsung TV. Telephone with free unlimited calling to USA, Canada, Mexico and US te …see more

from $89 / night

$595 - $695 / week

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from $89 / 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

(6) 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 $105 / night

$735 - $1,050 / week

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avg. 14 minutes

from $105 / night

(8) Very Good 

8

Vacation apartment in Hilton Head

Coastal South Carolina / Hilton Head

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Recently renovated two bedroom Admiral's Row Condo in the Hilton Head Beach and Tennis Resort. This is an ocean view unit and is located approximately 100 yards to one of the nicest beaches on Hilton Head Island. Unit includes two bedrooms, two baths and a beautiful ful …see more

from $150 / night

$1,050 / week

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from $150 / night

(1) Good 

29

Vacation home with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Trade the stresses of everyday life for complete relaxation and pristine beaches when you stay at this inviting 4-bedroom, 3-bathroom Hilton Head Island townhouse. Offering fantastic resort amenities and situated within proximity of the area's best attractions, this won …see more

from $171 / night

$1,199 - $2,245 / week

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avg. 13 minutes

from $171 / night

(6) Excellent 

24

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
Whether you are a golfer, tennis player, or sun and sand enthusiast, this unit is ideally located on Hilton Head - just a 5 minute walk to Coligny Plaza and one of the best beaches on the island. With 4 free bikes, you also have access to ride many miles on the islands' …see more

from $82 / night

$495 - $1,095 / week

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avg. 45 minutes

from $82 / night

29

Apartment rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
**NEWLY RENOVATED** Experience great outdoor living at its finest while staying at this secluded Hilton Head Island condo. Nestled in a quiet 4,000-acre gated community and surrounded by pristine nature and beauty, this 3-bedroom, 2-bathroom home comfortably sleeps 6 a …see more

from $149 / night

$1,043 - $1,575 / week

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avg. 19 minutes

from $149 / night

(2) Very Good 

40

Hilton Head Vacation apartment rental

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
In the mood for a peaceful oceanside getaway? Escape to this beautiful Hilton Head Island vacation rental condo. Nestled in an unspoiled natural preserve area, this comfortable unit is steps from "Hidden Beach" and surrounded by lush landscaping, wildlife, and stunning …see more

from $100 / night

$700 - $1,015 / week

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avg. 11 minutes

from $100 / night

29

Hilton Head Vacation home rental

Coastal South Carolina / Hilton Head

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This home has it all for the large multi-generation family or two families to share for the ideal week on Hilton Head in the South Beach area. Situated only a three minute walk to the beautiful Sea Pines Ocean Front, this home has a fabulous private pool for those time …see more

from $303 / night

$1,947 - $5,261 / week

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avg. 3 minutes

from $303 / 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 

9

Vacation condo rental

Coastal South Carolina / Hilton Head

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
Direct ocean front condo - The Breakers. Newly decorated with complete full kitchen. Best ocean view in all of Hilton Head. Park your car and relax at the beach. Fly a kite. Ride a bike. Short car ride to Harbour Town and popular South Beach. Walk to Coligny for restaur …see more

from $120 / night

$700 - $900 / week

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from $120 / 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

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 $122 / night

$854 / week

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avg. 2 hours 54 minutes

from $122 / 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
Elevate your Hilton Head Island experience by staying at this charming 2-bedroom, 1-bathroom vacation rental condo! Ideally situated in Palmetto Dunes, a short walk away from the Dunes House and a beautiful, family-friendly, Palmetto-Dunes-only beach, this home is perfe …see more

from $140 / night

$980 - $1,225 / week

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avg. 19 minutes

from $140 / night

(29) Very Good 

29

Condo rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Air conditioning
***We have renovated another unit in the same building so please ask us for more details if the date you want is unavailable or if you need more than one rental. This unit has a screened in balcony overlooking a lagoon. Both unit are in building 2 which is close to b …see more

from $75 / night

$500 - $950 / week

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from $75 / night

(22) Excellent 

22

Hilton Head Vacation apartment rental

Coastal South Carolina / Hilton Head

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
Just an 8-10 minute walk to beach access to South Forest Beach, via paved beach access, from our spacious and beautifully decorated 1250 square foot flat. The 2 BR and 2 full bath unit, with a queen sized sleep sofa in the living room, sleeps 6-7 guests. The master BR h …see more

from $175 / night

$770 - $1,050 / week

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avg. 3 hours 41 minutes

from $175 / 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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avg. 2 hours 1 minutes

from $85 / night

(7) Excellent 

21

Hilton Head 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
  • Ask about pets
HILTON HEAD ISLAND VILLA. These villas are professionally decorated for a first class visit to remember. You'll find a spacious living and dining area, fully equipped kitchen, and wet bar. The master bath has a Jacuzzi tub in these 1, 2, 3, and 4 bedroom villas. Wonderf …see more

from $250 / night

$1,372 - $2,620 / week

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from $250 / 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 see our other listing #9329452. Our Villas are located right next to the most "Family Oriented" pool and Clubhouse. Both jus …see more

from $90 / night

$450 - $940 / week

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avg. 39 minutes

from $90 / night

(3) Excellent 

18

Vacation villa rental

Coastal South Carolina / Hilton Head

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This Beachwalk townhouse located in Hilton Head Island's Shipyard Plantation is most likely the CLOSEST 3 BR CONDO TO THE BEACH in all of Shipyard Plantation. It will let you return to the idyllic summers of yesteryear, but with all of the modern amenities of today (3.5 …see more

from $225 / night

$1,435 - $1,625 / week

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avg. 3 hours 38 minutes

from $225 / night

24

Hilton Head Vacation villa rental

Coastal South Carolina / Hilton Head

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
If you are looking to reset your mind from your day-to-day work and re-energize your health with a vacation starting with a beautiful sunrise walk or run at the beach, followed by a challenging round of golf at one of the 3 beautiful golf courses and then play tennis at …see more

from $225 / night

$1,365 / week

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from $225 / night

(28) Excellent 

Certificate of Excellence

23

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 $105 / night

$650 - $950 / week

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avg. 15 minutes

from $105 / night

(4) Very Good 

20

Apartment 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
  • 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 $85 / night

$595 - $945 / week

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avg. 19 minutes

from $85 / night

(5) 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-bath house is the perfect home-away-from-home for a beach vacation, family getaway, golf, tennis or shopping weekend. An intimate neighborhood with only 14 homes, Bridgeport Lane is nestled inside Shipyard Plantation, o …see more

from $200 / night

$1,400 - $1,995 / week

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avg. 19 minutes

from $200 / night

29

Home rental in Hilton Head

Coastal South Carolina / Hilton Head

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Air conditioning
Step back in time and enjoy the beach, just a few hundred feet from the front door. This original Hilton Head beach cottage has been in the same family since it was built about 46 years ago. There is plenty of room for the entire family to enjoy time together. The large …see more

from $192 / night

$1,150 - $2,350 / week

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from $192 / night

10

Vacation condo with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Condo, 1 Bedroom, 1 Bath, (Sleeps 4) Direct oceanfront condo - The Breakers. Newly decorated with complete full kitchen. Best ocean view in all of Hilton Head. Park your car and relax at the beach. Fly a kite. Ride a bike. Short car ride to Harbour Town and popular So …see more

from $180 / night

$1,260 / week

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from $180 / night

(15) Very Good 

39

Vacation villa with shared pool, tennis court 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 0.3 mi
  • Swimming pool
Hello - you are invited to enjoy our newly renovated Hilton Head Island beach getaway home! The 2 story 2 bedroom villa comfortably sleeps 4. The home is bright, clean and adorable, located in a very quiet neighborhood that has 3 community pools and 1 tennis court for y …see more

from $125 / night

$800 - $1,600 / week

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avg. 3 hours 56 minutes

from $125 / night

(15) Very Good 

26

Vacation villa with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Swimming pool
Located in Fiddler's Cove, Hilton Head Island, a 23 acre resort community approximately a 5 minute walk to Folly Field Beach that includes showers, restrooms, and parking if you choose to drive, and is considered to be one of Hilton Head's widest and cleanest beaches. F …see more

from $85 / night

$595 - $910 / week

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avg. 1 hour 55 minutes

from $85 / night

(1) Excellent 

24

Vacation villa rental

Coastal South Carolina / Hilton Head

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
11 A Links is a bright, cheery, comfortable, single level villa located on Barony Golf Course of Port Royal.The living room has comfortable seating with a wet bar, cable TV, DVD player, Wireless Internet and a small reading area. The screened in porch and master bedroom …see more

from $299 / night

$1,095 - $1,899 / week

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from $299 / night

11

Villa rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Fully stocked kitchen, screened porch, across the street from soft court tennis facility golf course on other side of tennis master Biking and walking paths are everywhere. Bikes on the beach are fantastic. Kayaks are available nearby. Nature walks are abundant on and …see more

from $179 / night

$720 - $1,222 / week

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avg. 2 hours 3 minutes

from $179 / night

(23) Very Good 

Certificate of Excellence

29

Vacation home with swimming pool, golf nearby in Hilton Head

Coastal South Carolina / Hilton Head

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Ask about children
Located at the end of a peaceful cul de sac with a large private yard in Shipyard Plantation with golf views. Relax in the pool or on the deck while you watch the golfers go by. Our home has a 15 x 30 pool, several outdoor entertaining areas, as well as, a screen porc …see more

Certificate of Excellence

from $300 / night

$2,000 - $3,000 / week

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avg. 2 hours 16 minutes

from $300 / night

(12) Very Good 

22

Vacation villa rental

Coastal South Carolina / Hilton Head

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
HILTON HEAD ISLAND VILLA. These villas are professionally decorated for a first class visit to remember. You'll find a spacious living and dining area, fully equipped kitchen, and wet bar. The master bath has a Jacuzzi tub in these 1, 2, 3, and 4 bedroom villas. Wonderf …see more

from $187 / night

$1,026 - $1,943 / week

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from $187 / night

(1) Excellent 

28

Vacation villa in Hilton Head

Coastal South Carolina / Hilton Head

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This villa has been totally remodeled - new tile, carpet, kitchen cabinets and counter tops, eat in bar/buffet, appliances, as well as furnishings! A remodeled walk-in tile shower and Brazilian granite vanity were installed in the Master Bedroom. We also added a new ef …see more

from $115 / night

$650 - $990 / week

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avg. 2 hours 8 minutes

from $115 / 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 $99 / night

$693 - $1,043 / week

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avg. 19 minutes

from $99 / night