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100 Fairway Lane, Sea Pines: A Luxury Villa Stay

Welcome to all NEW BESTNEST/Luxe: An Elevated Experience in Vacationing, and our newest Luxe property at Unit 100 Fairway Lane Villas in Sea Pines. (200 Fairway Lane for mapping) Enjoy the ultimate in vacation rental accommodations on Hilton Head Island, featuring a carefully curated collection of homes and villas, chosen with the discerning traveler in mind, fabulously stocked, outfitted, and supported by your personal property concierge, available 24/7. STR Permit Number: 075152

Private Island in Hilton Head, Events & Poolside

Sleeps 26 on Your Own Private Island Near Hilton Head!Private 10-acre island retreat near Hilton Head that sleeps 26! Buck Island features two stunning homes designed for comfort and privacy. The main house offers 5 master suites (sleeps 10) and the guest house sleeps 16. Perfect for reunions, weddings, and retreats. Enjoy total seclusion while staying minutes from beaches, dining, and golf.True privacy. Unmatched space. One unforgettable experience. STR permit number 075124

74 Baynard Cove, Sea Pines: Pvt Pool, Fenced Yard

The perfect destination for family fun, this Hilton Head Island home has space for 10 and easy access to the bike paths that connect you to the beach, marina, and more within a short ride. When you’re not out at the beach, enjoy the spacious swimming pool at home in the private backyard. For dinner, dine alfresco on the screened porch or head to nearby restaurants around the marina. Copyright © Luxury Retreats. All rights reserved. STR Permit Number: 033122

Luxury 4BR Home w/ Pool & Golf Views - Sleeps 12

Heritage House is a newly redecorated 4BR/4BA retreat in Sea Pines, offering luxury, comfort, and golf course views. Sleeps 12 guests with spacious living areas, a private heated pool, fire pit, and screened porch. Enjoy new high-end furnishings, Smart TVs, and an open-concept kitchen. Just 1.1 miles to the beach, with bike rentals available for an additional fee. Pool is heated for free in March-May and September-November. 31 Heritage Road

44 Heritage, Sea Pines: Retreat on 11th Tee of HT

Set alongside the 11th tee box of the famous Harbour Town Links, this exclusive villa on Hilton Head Island is the perfect home base for your next golf vacation or family getaway. When you’re not out on the golf course, take a refreshing dip in the South Beach community pool or head down to the sandy beach. In the evening, check out South Beach Marina Village. Copyright © Luxury Retreats. All rights reserved. STR Permit Number: 076320

Architectural Masterpiece - Esthetic Stays

Immaculately cleaned and newly built, this 7,200 sq ft beach home is ideal for vacations, reunions, weddings, or retreats. Just a two-minute walk to the beach, it offers beautiful views and expansive living spaces. Located in the Bradley Beach area of Hilton Head Island, the home features four covered balconies, an infinity pool, two living rooms, ten bedrooms, and a private elevator—perfect for memorable group stays.

26 Tupelo, Sea Pines: Pool, Golf Views, Spacious

Capturing views of the golf course, this Hilton Head Island home is perfect for exciting, multi-family vacations. The guest house adds a little extra privacy, as do the mature trees surrounding the backyard’s pool and hot tub. When you’re ready to explore, ride the nearby bike paths to the South Beach Marina Village or the beach. Both only take a few minutes. Copyright © Luxury Retreats. All rights reserved.

Private Pool & Spa | Secluded | in Heritage Woods

Discover over 1,000 5-star reviews from our other properties! Heritage House is a spacious, elegant home in Sea Pines’ exclusive Heritage Woods. Centrally located, it’s just a ten-minute bike ride to the beach, Harbour Town, and South Beach Marina. Nestled at the end of a quiet cul-de-sac with bike paths in every direction, Heritage House offers unmatched privacy, tranquility, and convenience.

Walk2OldTown! Luxury Home + Carriage House

Just renovated! Interior Designer owned single family home + detached Carriage House for a total of 6 Bedrooms & 4 Full Baths! Huge park, playground, splash pad next door! Located in the heart of Bluffton’s coveted golf cart zone. Cruise or walk to Old Town in minutes for dinner, bar hopping, shopping, farmers markets, live music, or sunset on the May River. Ask about golf cart rentals!

3 Shore Crest, Free Golf, Game Room, Pickleball

3 Shore Crest Lane, Hilton Head Island. This custom-built 5-bedroom home in Burkes Beach offers luxury amenities including a chef's kitchen, sunroom, covered deck, pool table, private pool, and outdoor kitchen. With easy beach access and nearby amenities, it's the perfect vacation getaway. Plus, every reservation includes up to $1000 in FREE activities for an unforgettable experience.

July5discounted Oceanfront Pool & HotTub Elevator

Welcome to 63 Dune Lane, a brand-new oceanfront luxury vacation rental in North Forest Beach, Hilton Head Island. This stunning 7-bedroom, 8.5-bath beachfront home offers panoramic ocean views, a private pool and spa, elevator access, and direct beach entry, all within walking distance to dining, shopping, and Coligny Beach.

Oceanfront stunner w/ private pool & spa

This oceanfront stunner is nestled in Palmetto Dunes to offer guests direct access to one of Hilton Head's nicest beaches. Multiple living spaces and great separation between the bedrooms make this home perfect for groups and families!