Villa holiday rentals in Chatham County

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Top-rated villa rentals in Chatham County

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Top guest favourite

A spacious living area is furnished with a light grey sofa and armchairs, accented by decorative pillows. Two lamps provide soft lighting on side tables next to framed artwork. Natural light filters in through a large window, enhancing the warm and welcoming environment.

Villa in Hilton Head Island

4.98 out of 5 average rating, 58 reviews

Heart of Sea Pines|Tranquil 3BR Retreat|Beach*Pool

Light & spacious Heritage Villa in the heart of Sea Pines steps from Harbourtown's 1st Hole. Welcoming 3 Master-BR Suite villa w/ cathedral ceilings & deck. Just a 5 minute walk from the world-renown Harbourtown w/ shops, restaurants and live music for all ages. 8 minute bike ride to Sea Pines Beach Club. Beautiful shared pool, golf, tennis & pickleball, bike trails, award-winning playground, lagoon w/ gazebo for nature watching, amenities & beyond. Your perfect Spring Break or family vacation.

Guest favourite

Villa in Hilton Head Island

5 out of 5 average rating, 7 reviews

Honeymoon Delight! A Private Treehouse with Views!

A Honeymoon Paradise delight or for a small family! Located in the heart of Harbour Town on Deer Island, the Sea Loft villas offer a unique vacation experience with nature. This freestanding villa is located at the end of the cul-de-sac and offers sound views to the left and marsh views to the right. Enjoy watching all of the deer, birds and wildlife in this quiet paradise. Recently renovated with high end finishes, this villa will not disappoint the savvy traveler. No pets allowed.

Luxe

Villa in Hilton Head Island

1409 South Beach, Sea Pines: Stylish/Luxe Interior

Wake up each morning to the sound of palm trees rustling in the fresh sea breeze. Start your day with coffee on the porch while you relax in a sun chair. If you’re feeling more energetic, take that coffee for a stroll along the sandy beach, it’s just 50 meters from your back porch. If you feel like a swim, grabbing dinner, or checking out some luxury yachts, head for South Beach Marina Village. Copyright © Luxury Retreats. All rights reserved. STR Permit Number: 077262

Guest favourite

A modern living area features a gray sofa placed against a textured white brick wall. Above it, a round mirror reflects light. A minimalist coffee table sits in front, complemented by a small side table made of natural wood, with a piece of artwork hung above.

Villa in Savannah

4.78 out of 5 average rating, 220 reviews

The Grant by Black Swan - Heart of Downtown

Welcome to your industrial-modern loft getaway in Historic Downtown Savannah, where your daily living needs are preserved within our remarkably delightful spaces fit for working, relaxing, imbibing, and sleeping. Designed to converge both modern luxuries with tasteful nods to Savannah’s historic roots, each guest will enjoy our spaces featuring modern furnishings, Tuft & Needle mattresses, Parachute linens, Apple TVs, Public Goods amenities, local Perc coffee, and more.

A serene bedroom features a spacious bed with crisp, white bedding. A minimalist bedside table holds a simple lamp, and a tranquil piece of wall art depicting calm waves is displayed above the headboard, enhancing the room's peaceful ambiance.

Villa in Savannah

4.78 out of 5 average rating, 297 reviews

The Grant by Black Swan - Downtown Savannah

Superhost

Villa in Hilton Head Island

5 out of 5 average rating, 3 reviews

3BR Villa | Walk to Harbour Town & Marina

Stay in the heart of Harbour Town, just steps from the marina, lighthouse, shops, and dining. This charming villa offers a comfortable, coastal retreat perfect for couples or small groups. Enjoy easy access to Harbour Town Golf Links, scenic walking paths, and nearby beaches, all within minutes. With its unbeatable location and relaxed feel, this home is the perfect base for exploring Hilton Head and enjoying everything Sea Pines has to offer.

Guest favourite

A comfortable living area features a sectional sofa arranged around a glass-topped coffee table. A large television is mounted on the wall, and natural light fills the space from sliding glass doors that offer views of greenery outside.

Villa in Hilton Head Island

4.94 out of 5 average rating, 16 reviews

Great Blue Heron - an iTrip Hilton Head Home

Ready for a fresh start, peaceful downtime or a relaxing getaway in the serene & endless beauty of Sea Pines Resort on Hilton Head Island? Welcome to Great Blue Heron This freshly renovated & furnished Inland Harbour villa will help you de-stress, unwind and get back to your old self. As soon as you enter this home, the beautiful design & decor of this villa will welcome you and put you at ease.

Guest favourite

Villa in Hilton Head Island

4.75 out of 5 average rating, 16 reviews

Updated Sea Pines Villa • Walk to Harbour Town

Welcome to your renovated Sea Pines villa—a bright, modern retreat with peaceful lagoon views and an unbeatable location just a short walk to Harbour Town. Steps from the community pool and minutes from beaches, bike paths, shops, and dining, this updated 1-bedroom villa offers comfort, convenience, and true Lowcountry charm. STR Permit Number: 026796

Guest favourite

Villa in Hilton Head Island

5 out of 5 average rating, 7 reviews

2 King Suites | Walk to Harbour Town | Pool Access

Freshly updated 3-bedroom villa featuring a king suite with ensuite and two twin suites, each with a private full bath. Enjoy all-new dining, living, and game table furniture plus brand-new carpet in every bedroom. Perfect for families or groups, this villa offers stylish comfort and plenty of space to relax after a day of exploring Hilton Head.

Guest favourite

A sandy pathway is flanked by wooden posts leading toward the beach, with roped railings on either side. The ocean is visible in the distance under a clear blue sky, and the shoreline is lined with natural grasses and gentle waves.

Villa in Daufuskie Island

4.94 out of 5 average rating, 33 reviews

Daufuskie Island SC Spacious 3 Bedroom Ocean Front

Beautiful Oceanfront Villa on Daufuskie Island, SC is a place you can truly relax. Daufuskie Island sits between Hilton Head and Tybee Island (both visible from the Sandy Lane beach). While on Daufuskie Island you will want to explore the historical part of the island, visit local artisans, or just enjoy the beautiful beach with the white sand.

A sunlit sunroom is highlighted by large windows offering expansive views of the lagoon and first fairway of Atlantic Dunes Golf Course. Comfortable seating includes a light gray sofa and a dining table with four chairs, creating a serene atmosphere for relaxation and gatherings.

Villa in Hilton Head Island

4.63 out of 5 average rating, 24 reviews

Fairway One Villa Golf & Lagoon Views Walk to Beac

Welcome to 6956 Fairway One Villa~ The Heart of The Sea Pines Resort! 3 Bedroom Villa-across the street from Sea Pines Beach Club & next to Plantation Club Golf! Magnificent private front garden courtyard. Panoramic lagoon & golf views of the first fairway of Atlantic Dunes Golf Course. Spacious layout with all the amenities of home!

Superhost

Villa in Hilton Head Island

5 out of 5 average rating, 5 reviews

Luxe 2BR/2.5BA Villa - Walk to Harbour Town

Discover Stoney Splash, a charming 2BR/2.5BA villa in Sea Pines with marsh views and a private community pool just steps from your door. Walk or bike to Harbour Town, relax in coastal-inspired interiors, and dine al fresco on the patio. Sleeps 6 with king, queen, and sleeper sofa. Perfect for couples, families, or a peaceful escape.