Luxury rentals in Chatham County

Sea Pines Oceanfront

Palms and pines shade this classic beachfront cottage at Hilton Head’s Sea Pines. Shiplap walls, beamed ceilings, heart-pine floors, and wicker furniture are constant—and charming—reminders that you’re on the ocean, while a recent renovation brought in state-of-the-art appliances and an open modern layout. Cross the pool courtyard to the beach or take the trolley into town. Start the day with coffee and sunrise views on the screened-in porch, then move to a lounger by the private pool or an Adirondack chair that’s practically set on the sand. Finish a day at the beach with a waterfront dinner, served fresh from the barbecue at the alfresco table on the back porch. Beamed ceilings, crisp white walls, and pine floors lend Carolina charm to the open-plan great room on the home’s top floor. Gather on the slipcovered sofas, seat 10 to 12 in wicker chairs around a pine and zinc dining table, and perch at the breakfast bar in the fully equipped kitchen. Downstairs, you’ll find an inviting den stocked with board games and a TV. The ocean front pool has been refreshed with new tile and a new sandstone pool deck with 10 chic sling loungers. The adjoining lower patio has been enhanced with deep seating and an outdoor ping pong table, providing shady diversions for hot summer afternoons. A new dune deck with seating and outdoor shower connects the pool to the sand via a shapely new boardwalk over the dunes. And just above the pool deck, serious golfers and putt-putt enthusiasts alike will enjoy a new 4-hole putting green with ocean views. Not only is this villa right on the beach, its Sea Pines location puts you a short drive from a kid-friendly beach park with a splash pad. It’s also an easy drive to the golf course and about 10 minutes to shopping and dining in downtown Hilton Head. Or take one of the area’s trolley services to the picturesque Harbour Town marina.   Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with rain shower, Dual vanity, Television, Direct access to balcony, Ocean view • Bedroom 2: 2 Twin size beds, Ensuite bathroom with stand-alone shower, Television, Direct access to balcony • Bedroom 3: 2 Twin size beds, Ensuite bathroom with stand-alone shower, Television, Direct access to pool • Bedroom 4: 2 Twin size beds, Ensuite bathroom with stand-alone shower, Television, Direct access to garden • Bedroom 5: King size bed, Ensuite bathroom with rain shower, Television, Direct access to pool FEATURES & AMENITIES • More under “What this place offers” below OUTDOOR FEATURES • Screened porch STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions • Tennis at The Sea Pines Tennis Center or The South Beach Racquet Club • Boating, fishing, and crabbing at two different Marinas • Horseback riding and animal petting farm • More under “Add-on services” below

Lakefront Luxe: Pool, Spa, Cinema & Sportcourt

📸 East Point is a 7BR 6BA luxury home designed for unforgettable group stays in Savannah, GA. This spacious home features upscale furniture, premium decor, plush beds, home theater, game room & gym. Outdoor amenities such as pickleball, mini-golf, pool & spa that you can enjoy while basking in the views of the home's incredible backyard oasis. Located just 15 minutes from Savannah's downtown area, it also offers great convenience in exploring the city's rich history. Book your dream stay today!

Savannah 5BR Retreat, Hot Tub, Near Forsyth

This beautifully restored historic home is located in Savannah’s vibrant urban core, just a short walk from Forsyth Park. The home comfortably accommodates up to 10 guests and features 5 bedrooms and 3 full bathrooms across two thoughtfully designed floors. With professionally curated interiors, open concept living, kitchen, and dining spaces, and a private outdoor area complete with a hot tub, this upscale retreat offers the perfect blend of historic charm and modern comfort for group stays.

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 HHI Short Term Rental Permit : 064860

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

8 Heritage, Sea Pines: Private Pool, Walk to HT

Welcome to your home away from home in charming Hilton Head. Inside, earthy tones and wicker accents are set ablaze with natural light. Effortlessly transition from the contemporary indoors to the sprawling outdoor area which features plenty of space for al fresco dining and lounging under the sun. The spacious pool awaits to envelope you in a refreshing plunge. Stargaze with a glass of champagne. Copyright © Luxury Retreats. All rights reserved. STR Permit Number: 025998

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

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

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.

Downtown Riverfront Luxury, Steps to River Street

Discover Willow House, a modern waterfront townhome steps from Savannah’s Riverwalk! Ideal for groups, it sleeps 8 (2 Kings, 1 Queen, Sofa Bed) with private ensuite baths for every bedroom. Features chef-grade Wolf appliances, fireplace & river views. Walk minutes to the free shuttle for downtown access. Short drive to Tybee beaches. Upgrade for resort pool access. Book your unforgettable stay!

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.

Rare 8BR Savannah Retreat | Pool, Lake & Game Room

Welcome to your private Savannah estate — an 8-bedroom, 4-bath retreat for up to 16 guests, just a short drive from historic downtown Savannah and Tybee Island. Featuring a private pool, lake access, fire pit, and outdoor dining, this professionally designed home offers open-concept living spaces built for large groups.