Hilton Head 2027 Rentals

Total Price: $332,705

5 bedrooms

5 baths / 1 half bath

14 guests

5 (7)

**New to the rental market! This newly renovated Palmetto Dunes property offers 5 bedrooms, an eat in kitchen, outdoor seating, an oversized indoor pool (perfect for year round use in rain or shine) and a dock on the the famous 11 mile lagoon!** (note: duffy boat is not for guest use)FREE activities included with our signature Southern Hospitality

Never before rental!

new to the rental market! Be one of the first guests to enjoy this amazing Palmetto Dunes beach house!

85 Port Tack

Palmetto Dunes

Total Price: $229,230

5 bedrooms

3 baths / 1 half bath

11 guests

5 Shore Crest Lane is a newly constructed home that offers 6 bedrooms all with private bathrooms, a luxurious chef's kitchen, private heatable pool and heatable spa, and multiple entertaining areas. This property was built with renters in mind to ensure amazing memories are created and includes up to $1000 in FREE activities. 5 Shore Crest Lane

Special

Christmas In July

Celebrate Christmas in July with savings on your holiday Hilton Head getaway. Book a 4-night minimum stay between December 19 and January 2 and receive 10% off with promo code XMASINJULY. This limited-time offer is valid on new reservations only and ends July 31. Certain properties may be excluded, and the offer cannot be combined with any other discount.

5 Shore Crest Lane

Total Price: $463,408

6 baths / 1 half bath

20 guests

5 (22)

Welcome to 1 Surfwatch Way — a 2026 newly completed 6-bedroom 5.5-bath coastal retreat offering the very best of modern island living. Just a short 3–5 minute stroll to the beach, this exceptional home showcases all-new furnishings, appliances, and thoughtfully curated finishes throughout, creating a fresh and refined space for your Hil

Special

BOOK DIRECT AND SAVE!

Booking directly with Vacation Homes of Hilton Head rather than a third party site like VRBO, HomeAway, or AirBnb means that you save on service fees charged by those sites. In fact, some third party sites charge you, the guest, over 16% in service fees.

Make the most of your vacation by saving and booking directly with us. Plus, with our local expertise and knowledge, you get a whole different vacation experience when you book direct!

1 Surfwatch Way

Total Price: $381,434

5 baths / 2 half baths

20 guests

4.8 (5)

Enjoy the beautiful beach in the southeast on Hilton Head island at our newly remodeled beach condo! Oceanwalk Oasis sleeps 6 and boasts an outdoor pool AND and an indoor pool and hot tub! With two king bedrooms plus extra-long bunk beds, your family will enjoy plenty of space to kick back after a great day at the beach. Located just across t

Special

Christmas In July

411 Oceanwalk

Forest Beach

Total Price: $129,381

3 bedrooms

2 baths

6 guests

This property is now under new ownership and the owners are keen to make this already beautiful and spacious house lighter and brighter with a goal of blowing away all guests expectations! 4 Surf Watch Way is a magnificent 6-bedroom, 5.5-bathroom, pet friendly home accommodating up to 16 guests making it perfect for family reunions or large ga

Special

Christmas In July

4 Surfwatch Way

Total Price: $429,309

5 baths / 1 half bath

18 guests

4.9 (116)

10 Collier Beach, Hilton Head Island is an escape to paradise in this stunning 6-bedroom, 7-bathroom oceanfront home, offering breathtaking ocean views and the ultimate in privacy. Relax by the private pool, enjoy direct access to the beach, and indulge in the luxury of a chef's kitchen. Entertain friends and family in the game room, or let tee

Special

Christmas In July

10 Collier Beach Road

Singleton Beach

Total Price: $740,727

16 guests

4.9 (81)

This gorgeous home is just a short walk to the beach from a quiet seaside community in Burkes Beach. The lower floor houses the garage and a game area that looks out to the beautiful pool, which is great for family fun in the sun. The main floor has an open room concept where the kitchen, living room, and dining area flow into each other. There is

New Property Alert!

We are so excited to begin managing this property Spring 2026! Call us today to book this amazing rental property, perfect for any occasion!

4 Shore Crest Lane

Total Price: $412,429

19 guests

5 (3)

Discover a breathtaking new home on Shell Midden Lane, designed for the most discerning travelers. This exquisite property features 7 spacious bedrooms and 7.5 bathrooms, complete with a private pool and elevator. Spanning 4,639 square feet of heated living space, this low-country oasis perfectly balances comfort and elegance. With ample outdoor ar

Special

Christmas In July

110 Shell Midden

Forest Beach

Total Price: $426,925

7 bedrooms

18 guests

3 Surf Watch Way, Hilton Head is a 4,450 square foot home, located just steps from Burke's Beach, boasts an open concept floor plan perfect for entertaining. Enjoy family movie nights in the media room on the 2nd floor, equipped with a large flat-screen TV and recliners. The garage features a putting green, foosball table, air hockey, and arcad

Special

Christmas In July

3 Surf Watch Way

Total Price: $345,606

6 baths / 1 half bath

17 guests

4.9 (230)

EASY 5-6 MIN WALK TO BEACH: head straight down Hickory Lane, cross South Forest Beach, take foot path to beach access (in between Laurel and Juniper Lane)This exceptional property features 7 generously sized bedrooms and 7.5 bathrooms, complemented by a private pool and an elevator for added ease and accessibility. With 4,639 square feet of heated

Special

BOOK DIRECT AND SAVE!

Make the most of your vacation by saving and booking directly with us. Plus, with our local expertise and knowledge, you get a whole different vacation experience when you book direct!

120 Shell Midden

Forest Beach

Total Price: $472,001

7 bedrooms

18 guests

5 (1)