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, 47 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.

Superhost

Villa in Savannah

5 out of 5 average rating, 3 reviews

Savannah Retreat|Htd Pool|Pickleball|Hot tb|Golf

NEW LUXURY LISTING! Escape to your ultimate Savannah dream retreat! Heated Swimming Pool, Pickleball Court, Hot Tub, Mini Golf, Bowling Alley, Poker Room, Home Theatre, Pool Table, FoosBall, Shuffle Board, Arcade Games - all now available at once place Indulge in the perfect blend of Southern elegance and modern comfort in this brand-new, expansive 6-bedroom estate. Designed for unforgettable group experiences, it’s the ideal for bachelorette celebrations, family reunions, or group getaways.

Superhost

Villa in Hilton Head Island

New place to stay

Walk to Harbour Town | Scenic Villa | Sleeps 7

Tucked away in the heart of Sea Pines Resort, this beautifully situated villa offers a classic Hilton Head escape with peaceful marsh views and unbeatable proximity to Harbour Town Marina, just steps from your door. Surrounded by towering oaks and serene Lowcountry scenery, 265 Stoney Creek Villa blends walkable convenience with relaxed coastal charm. Comfortably sleeping up to 7 guests and offering access to the Stoney Creek Community Pool, this villa is perfect for couples and families!

Superhost

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

4.76 out of 5 average rating, 196 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

4.77 out of 5 average rating, 283 reviews

The Grant by Black Swan - Downtown Savannah

Guest favourite

A spacious living area features a large blue sectional sofa with decorative pillows, two matching armchairs, and a stylish coffee table. The room is illuminated by natural light from expansive windows, offering views of the surrounding greenery. A dining area with a chandelier is visible in the background.

Villa in Hilton Head Island

5 out of 5 average rating, 9 reviews

1102 Harbour South Club Villa Harbour Town

Nestled in the heart of Harbour Town, this beautifully updated and professionally designed Harbour South Club Villa offers the perfect blend of luxury, comfort, and convenience. Whether you're visiting for the RBC Heritage, planning a golf getaway, or enjoying a family vacation, this exquisite villa is your ideal retreat. Community Pool Open April 1st-October 1st. Beach Access via the Sea Pines Trolley.

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

5 out of 5 average rating, 14 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.

Superhost

Villa in Hilton Head Island

4.86 out of 5 average rating, 7 reviews

Cozy Villa w/ Private Deck in Heart of Sea Pines

-Private Deck w/ BBQ -Newly Renovated -2 Free Adult Bikes (Valid for stays from 3 - 21 nights) -Pet-Friendly Welcome to Stoney Creek Villa 249, your ultimate relaxing and comfortable getaway located in the heart of Harbourtown on Hilton Head Island. This newly renovated one-bedroom villa boasts modern and upscale furnishings, providing a stylish and inviting retreat for up to four guests.

Superhost

A bright living room features a comfortable light gray sofa adorned with decorative pillows. A wooden coffee table sits in the center, complemented by a bowl of fresh fruit. Floor-to-ceiling sliding doors offer a view of the water and the Harbour Town Lighthouse.

Villa in Hilton Head Island

4.83 out of 5 average rating, 6 reviews

Penthouse condo with sunset water views

🏆 We're a Superhost located in Hilton Head Island with 700+ fantastic property reviews. Voted LowCountry's Best year after year, your group is sure to enjoy your next Hilton Head Island escape in this stunning property ⛵️ Harbour Town Penthouse | Sound & Harbour Town Lighthouse Views ⛳️ Save even more when you book 1041 Caravel Court and receive $300 in complimentary daily activities

Guest favourite

Villa in Hilton Head Island

5 out of 5 average rating, 5 reviews

Pet Friendly Villa Near Beach with Pool Access

Lookout Lagoon is a spacious 3-bedroom, 3-bath South Beach villa that sleeps 6 and sits just 0.3 miles from the beach. This pet-friendly retreat offers peaceful lagoon views, three private en-suite bedrooms, and 1,900+ sq ft of living space. Walk to marina dining and pickleball, and enjoy Harbour Town Pool access for 2026. A relaxed, location-driven Sea Pines getaway.

Top 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

4.92 out of 5 average rating, 26 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.

Guest favourite

Villa in Hilton Head Island

4.89 out of 5 average rating, 9 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.