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

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1,228 Vacation rentals

10

Vacation villa in Hilton Head

Coastal South Carolina / Hilton Head

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • 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 comfortably). …see more

from $100 / night

$600 - $750 / week

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from $100 / night

12

Hilton Head Vacation condo rental

Coastal South Carolina / Hilton Head

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
HILTON HEAD ISLAND, SOUTH CAROLINA, USA. "SMILING FACES, BEAUTIFUL PLACES" PRETTY 2 BED/2 BATHROOM CONDO IN FIDDLERS COVE, 3 MINUTES WALK FROM AWARD WINNING BEACH. GOLFERS PARADISE. CYCLE THE ISLAND, GO TO THE GYM, PLAY TENNIS IN 10 TENNIS COURTS ON SITE, 2 LARG …see more

from $135 / night

$875 / week

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from $135 / night

32

Villa rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The Island: Hilton Head Island may only be 12 miles by 5 miles wide, but you’ll find everything you need here for the ultimate Island retreat. Enjoy days basking in the sun on some of the best beaches in the country. Get into the swing of things at your choice of 24 wor …see more

from $90 / night

$525 - $1030 / week

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from $90 / night

17

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
This private 21 acre oceanfront community has 24 hour gated security and a private pier with beach access. The Spa features an indoor heated pool and hot tub, 2 outdoor pools, 3 tennis courts and an exercise room all surrounded by old live oak trees in a secluded locati …see more

from $75 / night

$500 - $925 / week

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from $75 / night

(21) Excellent 

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

from $125 / night

$750 - $950 / week

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from $125 / night

(19) Very Good 

12

Hilton Head Vacation villa rental

Coastal South Carolina / Hilton Head

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Enjoy the sunset and sunrise from this private elevated first floor direct oceanfront unit in the gated community of Seaside Villas. Walk less than 100 steps to the beach. If you love the sea, this panoramic view will not disappoint!. Our villa is elegantly decorated w …see more

from $150 / night

$800 - $975 / week

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from $150 / night

(19) Very Good 

26

Condo rental in Hilton Head with shared pool

Coastal South Carolina / Hilton Head

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Air conditioning
We are the sister property of The Sandy Feet Retreat - read our great reviews - we promise to have the same service at The Bare Feet Beach Retreat! This unit has a screened in balcony overlooking a lagoon. Both unit are in building 2 which is close to boardwalk to bea …see more

from $75 / night

$475 - $850 / week

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from $75 / 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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from $61 / night

25

Vacation home with shared 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 5 mi
  • Swimming pool
  • Child friendly
Do you want to enjoy natural beauty, peaceful privacy and easy access to recreation, terrific restaurants and stores? We welcome a pet visitor for stays of a month or longer. Please do not ask for stays shorter than this unless you like our long stay guests will pay $1 …see more

from $150 / night

$995 - $1265 / week

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from $150 / 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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from $90 / night

51

Vacation home in Hilton Head

Coastal South Carolina / Hilton Head

7 20 Min stay varies

  • 7 bedrooms
  • Sleeps 20
  • Min stay varies
  • Ask about children
  • Ask about pets
Harbour Town Jewel is a brand new home in Sea Pines Plantation designed with a contemporary flair and meticulous attention to detail. It has 7 bedrooms, 7.5 baths and can sleep up to 20 people ? an ideal size for multiple families or large groups. The house is located o …see more

from $800 / night

$3999 - $7999 / week

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from $800 / night

(9) Very Good 

20

Vacation apartment with shared pool, golf nearby in Hilton Head

Coastal South Carolina / Hilton Head

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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

(3) 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 a prime South Forest Beach. 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 man …see more

from $105 / night

$735 - $1050 / week

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from $105 / 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 - $900 / week

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from $100 / night

(1) Excellent 

25

Hilton Head Vacation condo rental

Coastal South Carolina / Hilton Head

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Come enjoy a getaway on a beautiful island that is filled with many things to do or to just relax! Our condo is on the 1st floor and has 2 bedrooms with queen beds, and 2 full baths. We use our own quality sheets and towels to make you feel more at home. There is a TV a …see more

from $104 / night

$725 - $826 / week

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from $104 / night

25

Vacation condo 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
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Sun, Sand, Surf, Tennis and Golf! Just what a dream vacation is made of!. Come join us at our Hilton Head Villa for an unforgettable value vacation! Choose Hilton Head Island for the fantastic beaches and weather. Stretch your vacation dollars at the fully outfitted H …see more

from $85 / night

$500 - $750 / week

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from $85 / night

28

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 - $2317 / week

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from $207 / night

(21) Excellent 

22

Hilton Head Vacation apartment rental

Coastal South Carolina / Hilton Head

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • 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 $145 / night

$776 - $925 / week

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from $145 / night

(4) Excellent 

26

Vacation home 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
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 $180 / night

$1200 - $1960 / week

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from $180 / night

21

Vacation villa in Hilton Head

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Perfect beach get away in gated resort for couple or families. Enjoy balcony with lagoon and salt marsh view, distant ocean view. Short walk on private boardwalk or take shuttle to beach. Swim in indoor or outdoor pools and take a stroll on indoor jogging path or wor …see more

from $120 / night

$620 - $795 / week

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from $120 / night

(4) Excellent 

22

Villa rental 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
This lovely unit with partial ocean view in a quiet gated community is located just steps from the beautiful beach of Port Royal Sound. NEW LISTING owned now by same owner as the popular unit VRBO #268399. It has a new renovated kitchen with beautiful tile backsplash …see more

from $90 / night

$630 / week

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from $90 / night

(30) 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

21

Vacation home with golf nearby in Hilton Head

Coastal South Carolina / Hilton Head

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
The location and setting of 15 Wagon Rd is excellent. Unique style home with original features. 4 Bedrooms. 3 Full Bathrooms. Sleeps 12. 1 King, 1 Queen, 7 Twins. 1 Full. 5 Minute Walk to the Beach. 5 TVs | Blu-Ray DVD | Bluetooth Stereo | Free WiFi. Point Central Key …see more

from $250 / night

$1495 - $3496 / week

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from $250 / night

8

Vacation apartment with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
2 Bedroom with Queen beds, 2 Bath Kid-friendly Villa With ' Hidden Beach ' Let us make your getaway special... Start your morning at this peaceful island retreat with a walk along the water to watch the sunrise. If you appreciate attention to detail, tasteful decor, …see more

from $125 / night

$875 / week

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from $125 / night

(18) Excellent 

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

from $115 / night

$725 - $985 / week

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from $115 / night

(3) Excellent 

27

Vacation villa with shared pool, golf nearby in Hilton Head

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

from $90 / night

$600 - $850 / week

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from $90 / night

(1) Excellent 

24

Vacation villa 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
Planning a Golf getaway or tennis vacation? Attending a Wedding? Attending a Conference at the Sonesta? Consider staying at our Beautiful Villa! Our Hilton Head Island villa is located in Shipyard Plantation at The Greens - Unit 170, a secure, gated community. Newly R …see more

from $139 / night

$795 - $1150 / week

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from $139 / night

28

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 times …see more

from $303 / night

$1946 - $4844 / week

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from $303 / night

18

Hilton Head Vacation condo rental

Coastal South Carolina / Hilton Head

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Come to Hilton Head and enjoy one of the islands best beaches. We stayed at Hilton Head Beach and Tennis and fell in love with it. There is everything you need right here. On-site restaurant, store, bike rental, two pools (oceanfront), shuffleboard, FREE children's prog …see more

from $125 / night

$750 - $1295 / week

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from $125 / night

(5) Excellent 

24

Home rental in Hilton Head with golf nearby

Coastal South Carolina / Hilton Head

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
This home is convenient to all the best HHI has to offer, as well as, enjoying the privacy of a quiet neighborhood with a great view of the lagoon from almost every room. Enjoy coffee/breakfast on the patio. Then take a leisurely walk or bike ride to the beach, communi …see more

from $320 / night

$1850 - $2295 / week

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from $320 / night

26

Hilton Head Vacation villa rental

Coastal South Carolina / Hilton Head

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Beautifully decorated 3rd floor ocean view villa located in the heart of Hilton Head Island. Just steps to the beach and walking distance to shops, restaurants and attractions. The villa features a fully equipped modern kitchen, a Mitsubishi split A/C system, and privat …see more

from $90 / night

$567 - $880 / week

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from $90 / night

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
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Prepare to relax at the Spa at Port Royal Sound. This lovely, third-floor, 2-bed, 2-bath villa comfortably sleeps 6 people and is surrounded by stunning coastal scenery. The moment you arrive, you’ll be encompassed by natural beauty outside - and in.  When you walk thr …see more

from $105 / night

$654 - $1155 / week

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from $105 / night

(1) Excellent 

26

Hilton Head Vacation condo rental

Coastal South Carolina / Hilton Head

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
St Andrews Common is a quiet and private community with a crystal clean swimming pool, sun deck and tranquility pond that overlooks the neighboring golf course. We are just inside the Palmetto Dunes Plantation, considered one of the finest destinations in the world and …see more

from $105 / night

$490 - $1021 / week

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from $105 / night

(2) Very Good 

22

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

$800 / week

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from $75 / 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 - $737 / week

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from $94 / night

32

Hilton Head Vacation home rental

Coastal South Carolina / Hilton Head

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to "Happy Ours" at 8 Wildwood Ct. - a beach, golf, tennis and yachting oriented, re-inspired coastal home nestled in Greenwood Forest inside the prestigious gates of Sea Pines Plantation. We have loved being Sea Pines property owners for over the last 5 years. W …see more

from $260 / night

$1525 - $3101 / week

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from $260 / night

(2) Very Good 

12

Vacation apartment with shared pool in Hilton Head

Coastal South Carolina / Hilton Head

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • 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 $125 / night

$700 - $900 / week

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from $125 / night

(8) Very Good 

Certificate of Excellence

35

Hilton Head Vacation apartment rental

Coastal South Carolina / Hilton Head

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Sun, Sand, Surf, Tennis and Golf! Just what a dream vacation is made of!. Come join us at our Hilton Head Villa for an unforgettable value vacation! Choose Hilton Head Island for the fantastic beaches and weather. Stretch your vacation dollars at the fully outfitted H …see more

Certificate of Excellence

from $79 / night

$500 - $675 / week

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from $79 / night

(29) Excellent 

27

Hilton Head Vacation apartment rental

Coastal South Carolina / Hilton Head

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Our property was just renovated May 2014 and is within walking distance to the beach. We have recently purchased another unit in the same building which we are renovating. If the date you want is not available or if you are looking to rent more than one unit, please c …see more

from $70 / night

$475 - $850 / week

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from $70 / night

23

Hilton Head Vacation villa rental

Coastal South Carolina / Hilton Head

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
This beautifully furnished villa is very kid friendly and offers all the amenities you want to make your vacation on Hilton Head Island one you will want to repeat every year. Three pools, access to almost 100 miles of biking and walking paths, tennis courts, and of cou …see more

from $111 / night

$699 - $995 / week

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from $111 / night

1