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Our top choices for Hilton Head Island vacation homes

1. Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380

Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380
South End
9.6 out of 10, Exceptional, (109 reviews)
"Awesome spot to stay with everything we needed. Really enjoyed the pool access, walking distance to the beach, and bikes included with the property."
United States
Will K.
The price is ¥14,263
¥46,894 total
includes taxes & fees
Nov 9 - Nov 10
Awesome Ocean View! Coligny Area! Updated and CLEAN 1 Bedroom! #380

2. Beach. View. Suite. 1 br. 1 ba. Sleeps 5

Beach. View. Suite. 1 br. 1 ba. Sleeps 5
Mid Island
9.6 out of 10, Exceptional, (124 reviews)
"Would stay again!"
United States
Shandi B.
The price is ¥9,390
¥35,956 total
includes taxes & fees
Nov 15 - Nov 16
Beach. View. Suite. 1 br. 1 ba. Sleeps 5

3. Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown

Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown
Sea Pines
10.0 out of 10, Exceptional, (114 reviews)
"Beautiful, quiet property."
United States
marian h.
The price is ¥26,815
¥62,444 total
includes taxes & fees
Dec 1 - Dec 2
Stunning Sea Pines Treetop Oasis Deck & Grill with short walk to Harbourtown

4. Mid-Island Retreat | Pool | Beach Gear | Pets OK

Mid-Island Retreat | Pool | Beach Gear | Pets OK
Mid Island
The price is ¥8,558
¥34,501 total
includes taxes & fees
Nov 10 - Nov 11
Mid-Island Retreat | Pool | Beach Gear | Pets OK

5. Disney's Hilton Head Island Resort

Disney's Hilton Head Island Resort
3.5 star property
Mid Island
9.6 out of 10, Exceptional, (131 reviews)
"The room and property were incredible! Already booking my next stay"
United States
Melissa
Disney's Hilton Head Island Resort

6. Old Town + Home & Carriage House + EV Charger

Old Town + Home & Carriage House + EV Charger
Old Town Bluffton
9.6 out of 10, Exceptional, (7 reviews)
"We thoroughly enjoyed our stay! The home is lovely and the location is unbeatable. We were able to walk everywhere in Bluffton and enjoy its southern charm. "
United States
Anonymous traveler
The price is ¥25,293
¥91,248 total
includes taxes & fees
Nov 16 - Nov 17
Old Town + Home & Carriage House + EV Charger

7. 6BR Hilton Head Beach House W/Pool, Fire Pit, Elev

6BR Hilton Head Beach House W/Pool, Fire Pit, Elev
Mid Island
9.2 out of 10, Wonderful, (68 reviews)
"Great spot…wish we had booked our entire stay there. Would definitely go back. "
United States
Ohly917
The price is ¥27,718
¥107,742 total
includes taxes & fees
Nov 15 - Nov 16
6BR Hilton Head Beach House W/Pool, Fire Pit, Elev

8. Luxe Family Gem-FREE Heated Pool~Walk to Beach~BBQ

Luxe Family Gem-FREE Heated Pool~Walk to Beach~BBQ
Mid Island
9.2 out of 10, Wonderful, (86 reviews)
"Wonderful time at our stay! The house is very well stocked and great location! "
United States
sara e.
The price is ¥30,238
¥110,762 total
includes taxes & fees
Nov 10 - Nov 11
Luxe Family Gem-FREE Heated Pool~Walk to Beach~BBQ

9. Nature Lovers Love 2033 Deer Island Treehouse Walkable to Harbour Town

Nature Lovers Love 2033 Deer Island Treehouse Walkable to Harbour Town
Sea Pines
9.2 out of 10, Wonderful, (40 reviews)
"Loved the location, the condo had everything we needed, and the host was great to work with."
United States
Scott R.
The price is ¥20,111
¥66,577 total
includes taxes & fees
Nov 9 - Nov 10
Nature Lovers Love 2033 Deer Island Treehouse Walkable to Harbour Town

10. NEW! 3 mins to Old Town • Sleeps 12 • Game Room • Charming Bluffton Retreat

NEW! 3 mins to Old Town • Sleeps 12 • Game Room • Charming Bluffton Retreat
Bluffton
9.8 out of 10, Exceptional, (10 reviews)
"everything was great for our family trip!"
United States
Grace M.
The price is ¥18,477
¥79,560 total
includes taxes & fees
Nov 9 - Nov 10
NEW! 3 mins to Old Town • Sleeps 12 • Game Room • Charming Bluffton Retreat

11. Two Fawns at Sea Pines-4+BR-Group Friendly-New Heated Pool & Spa,Dog Friendly

Two Fawns at Sea Pines-4+BR-Group Friendly-New Heated Pool & Spa,Dog Friendly
Sea Pines
The price is ¥39,509
¥113,541 total
includes taxes & fees
Nov 9 - Nov 10
Two Fawns at Sea Pines-4+BR-Group Friendly-New Heated Pool & Spa,Dog Friendly

12. Treehouse at BootLegger Cove

Treehouse at BootLegger Cove
Old Town Bluffton
10.0 out of 10, Exceptional, (4 reviews)
"The Treehouse exceeded our expectations! It was so well appointed, clean and prefect for our needs. The hosts were beyond nice and helpful. We will definitely stay there again!"
United States
Karen P.
The price is ¥34,073
¥65,373 total
includes taxes & fees
Nov 9 - Nov 10
Treehouse at BootLegger Cove

13. Mins to Downtown & Beach, Sleeps 10, Pool

Mins to Downtown & Beach, Sleeps 10, Pool
Bluffton
10.0 out of 10, Exceptional, (2 reviews)
"We had a fantastic stay! Kaila was flexible, accommodating, and extremely responsive, making everything easy from start to finish.The house was spotless, spacious, and beautifully decorated — very comfortable and welcoming. The central location was a huge bonus, with easy access to great restaurants and shops.We’d absolutely stay here again. Highly recommend!"
United States
Jared B.
The price is ¥31,379
¥103,408 total
includes taxes & fees
Nov 11 - Nov 12
Mins to Downtown & Beach, Sleeps 10, Pool

14. Two Homes · Walk to Old Town · Fire Pit · EV

Two Homes · Walk to Old Town · Fire Pit · EV
Old Town Bluffton
10.0 out of 10, Exceptional, (6 reviews)
"We had an incredible weekend. Everything was perfect!! The rental is beautiful and in perfect proximity to Old Town Bluffton. "
United States
Ashley G.
The price is ¥29,536
¥96,353 total
includes taxes & fees
Nov 9 - Nov 10
Two Homes · Walk to Old Town · Fire Pit · EV

15. Montage Palmetto Bluff Residences

Montage Palmetto Bluff Residences
5.0 star property
Palmetto Bluff
10.0 out of 10, Exceptional, (2 reviews)
"Very family friendly. Parking was a problem Check in was not one minute early. House was beautiful and very clean. Pool was wonderful Prices were high but we knew that ahead of time"
United States
john j
The price is ¥238,512
¥284,356 total
includes taxes & fees
Nov 15 - Nov 16
Montage Palmetto Bluff Residences

16. Newly Renovated Duplex- 4th Row

Newly Renovated Duplex- 4th Row
Mid Island
9.8 out of 10, Exceptional, (15 reviews)
"Excellent location and a dog friendly beach"
United States
Brandon H.
The price is ¥23,614
¥66,448 total
includes taxes & fees
Nov 9 - Nov 10
Newly Renovated Duplex- 4th Row

17. Old Town + Modern + Fire Pit + EV Charger

Old Town + Modern + Fire Pit + EV Charger
Old Town Bluffton
9.4 out of 10, Exceptional, (32 reviews)
"We have a lovely stay over the 4th of July. Perfectly located! The house was clean and well appointed. Check in was smooth and the hosts were very accessible."
United States
Mariah M.
The price is ¥26,815
¥70,544 total
includes taxes & fees
Dec 3 - Dec 4
Old Town + Modern + Fire Pit + EV Charger

18. Spacious Bluffton Getaway Near Hilton Head Sleeps Big Groups Golf & Beaches

Spacious Bluffton Getaway Near Hilton Head Sleeps Big Groups Golf & Beaches
Bluffton
The price is ¥32,144
¥99,859 total
includes taxes & fees
Nov 9 - Nov 10
Spacious Bluffton Getaway Near Hilton Head Sleeps Big Groups Golf & Beaches

19. The Bluffton Farmhouse

The Bluffton Farmhouse
Bluffton
10.0 out of 10, Exceptional, (126 reviews)
"Amazing place and host will for sure stay again"
United States
Jeffery A.
The price is ¥35,658
¥75,833 total
includes taxes & fees
Nov 9 - Nov 10
The Bluffton Farmhouse

20. Walk to Beach, 8BR, Heated Pool, Sauna, Elevator

Walk to Beach, 8BR, Heated Pool, Sauna, Elevator
Mid Island
8.0 out of 10, Very good, (6 reviews)
"Perfect, for a large family trying to vacation together. Plenty of space for everyone to sleep and for everyone to hang out."
United States
Theresa E.
The price is ¥28,390
¥117,120 total
includes taxes & fees
Nov 9 - Nov 10
Walk to Beach, 8BR, Heated Pool, Sauna, Elevator
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hilton Head Island and related destinations

Pristine beaches with packed sand perfect for biking stretch for 12 miles along this laid-back coastal paradise. Golf enthusiasts can play world-class courses while nature lovers spot alligators and herons in the Pinckney Island Wildlife Refuge.

A coastal town with a lighthouse, marina, and golf course.

Top reviews in Hilton Head Island