Hilton Head 2027 Rentals
Secure the Best Properties for 2027 Before They're Gone!
Hilton Head Island is America’s favorite coastal escape. With its pristine Atlantic beaches, championship golf courses, and moss-draped maritime forests, prime properties book up up to a year in advance.
Island Insider Tip: Looking for the ultimate spring break or holiday getaway? Demand for the 2027 Easter season (late March/April) and summer weeks is already exceptionally high. Don't wait until the best weeks are taken!
Explore Our Featured 2027 Rental Categories
Whether you want a sprawling private estate for a multi-generational family reunion or a cozy oceanside condo for a romantic retreat, we have the perfect home base for your Lowcountry adventures..
8 properties available
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
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
35 Full Sweep, Hilton Head Island is a recently renovated 5-bedroom/5-bathroom home, located inside Palmetto Dunes Plantation, features a large private pool and new furniture throughout. With 3 King Primary bedrooms, each with private en-suite bathrooms, and a fourth bedroom with a pullout sofa and work space, it accommodates various needs. The lar
**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
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
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
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
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
Tell us what you're looking for and someone will contact you with available options.