Lock in your stay with a low deposit

Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.

Lock in your stay with a low deposit of $550 on homes & $350 on villas!

Valid for any booking between 9/1/26 - 3/31/27.

We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.

This offer cannot be combined with other offers. Valid for new stays only.

135 properties available

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This home is a stunning haven nestled in the heart of Sea Pines, where luxury meets comfort in a beautiful retreat. Step inside and feel the warmth of this exquisitely remodeled 18 Willow Oak. Beautiful 8-inch wood flooring guides you through the open layou

Special

Lock in your stay with a low deposit

Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.

Lock in your stay with a low deposit of $550 on homes & $350 on villas!

Valid for any booking between 9/1/26 - 3/31/27.

We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.

This offer cannot be combined with other offers. Valid for new stays only.

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 504 Barrington Arms is a lovely three-bedroom, three-bathroom direct oceanfront condo on the fifth floor. Enjoy panoramic ocean views and updated furnishings and décor throughout. The dining area is adjacent to both the living room and the well-equipped kitch

Special

Lock in your stay with a low deposit

Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.

Lock in your stay with a low deposit of $550 on homes & $350 on villas!

Valid for any booking between 9/1/26 - 3/31/27.

We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.

This offer cannot be combined with other offers. Valid for new stays only.

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. No details were missed in this amazing 3-bedroom Palmetto Dunes home. Amazing golf course views greet you as soon as you walk in the door. The large living room\'s main sitting area has a sleeper sofa, a loveseat, and a desk. Heading further through this ho

Special

Lock in your stay with a low deposit

Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.

Lock in your stay with a low deposit of $550 on homes & $350 on villas!

Valid for any booking between 9/1/26 - 3/31/27.

We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.

This offer cannot be combined with other offers. Valid for new stays only.

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This stunning home has recently undergone a series of thoughtful updates designed to enhance both comfort and style. A brand new fifth bedroom has been added, now featuring a comfortable queen bed to provide additional sleeping accommodations. The property ha

Special

Lock in your stay with a low deposit

Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.

Lock in your stay with a low deposit of $550 on homes & $350 on villas!

Valid for any booking between 9/1/26 - 3/31/27.

We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.

This offer cannot be combined with other offers. Valid for new stays only.

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This fantastic 2nd row of the ocean is nestled in the palms of the Palmetto Dunes resort. With 6 bedrooms and 6.5 baths, this low-country home is the perfect getaway for family and friends! A circular drive leads to a beautiful entrance way and wraparound p

Special

Lock in your stay with a low deposit

Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.

Lock in your stay with a low deposit of $550 on homes & $350 on villas!

Valid for any booking between 9/1/26 - 3/31/27.

We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.

This offer cannot be combined with other offers. Valid for new stays only.

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This completely renovated (2024) 2 bedroom, 2 bathroom property is perfectly located within steps of South Beach Marina, a short five minute walk to South Beach, and a three minute walk to tennis, pickleball, The Salty Dog Café, restaurants, and shopping. T

Special

Lock in your stay with a low deposit

Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.

Lock in your stay with a low deposit of $550 on homes & $350 on villas!

Valid for any booking between 9/1/26 - 3/31/27.

We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.

This offer cannot be combined with other offers. Valid for new stays only.

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Can you just imagine hearing the birds chirping and the wildlife rustling in the greenery as you watch the herons wading in the lagoon? Can you hear the ping of the golfer\'s tee shot? Is the contact between the driver and the golf ball making the sweetest so

Special

Lock in your stay with a low deposit

Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.

Lock in your stay with a low deposit of $550 on homes & $350 on villas!

Valid for any booking between 9/1/26 - 3/31/27.

We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.

This offer cannot be combined with other offers. Valid for new stays only.

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. 2517 Windsor Place is a beautifully appointed three-bedroom, three-bathroom oceanfront villa that blends spacious design with effortless coastal elegance. Ideal for golf getaways, family vacations, or couples traveling together, this villa offers a thoughtful

Special

Lock in your stay with a low deposit

Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.

Lock in your stay with a low deposit of $550 on homes & $350 on villas!

Valid for any booking between 9/1/26 - 3/31/27.

We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.

This offer cannot be combined with other offers. Valid for new stays only.

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This Palmetto Dunes beach home features 4 bedrooms and is only a short walk to the beach—that is, if you ever want to leave this gem! 15 Sea Lane features a spacious open floor plan and plenty of natural sunlight! Unwind in the living room as you watch TV on

Special

Lock in your stay with a low deposit

Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.

Lock in your stay with a low deposit of $550 on homes & $350 on villas!

Valid for any booking between 9/1/26 - 3/31/27.

We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.

This offer cannot be combined with other offers. Valid for new stays only.

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Penthouse 3-bed villa overlooking the world-famous Harbour Town Yacht Basin, just steps away from Harbourtown A great room with dual sofas facing a large flat-screen TV A set of sliders gives entrance to a whimsically tiled patio with a postcard-perfect view

Special

Lock in your stay with a low deposit

Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.

Lock in your stay with a low deposit of $550 on homes & $350 on villas!

Valid for any booking between 9/1/26 - 3/31/27.

We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.

This offer cannot be combined with other offers. Valid for new stays only.

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. Nestled in the charming Burke\'s Beach on Hilton Head Island, this remarkable 6-bedroom, 5 1/2-bathroom home is a coastal paradise that offers a luxurious and comfortable lifestyle. As you step inside, you\'ll be greeted by a spacious and well-designed interi

Special

Lock in your stay with a low deposit

Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.

Lock in your stay with a low deposit of $550 on homes & $350 on villas!

Valid for any booking between 9/1/26 - 3/31/27.

We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.

This offer cannot be combined with other offers. Valid for new stays only.

Welcome to this distinctive vacation property managed locally by Island Time Hilton Head. This property will be undergoing construction and unavailable for rental during 2026. If you have any questions, please reach out to us at or call This beautifully upgraded vacation home combines sophisticated design, high-end finishes, and abundant natur

Special

Lock in your stay with a low deposit

Golden evenings and a quieter island rhythm make this one of the best times to visit Hilton Head. Plan ahead and secure your dates for a fall escape, holiday visit, or early spring getaway.

Lock in your stay with a low deposit of $550 on homes & $350 on villas!

Valid for any booking between 9/1/26 - 3/31/27.

We have no hidden fees! Our pricing is transparent, so what you see is what you are paying. Click here to see our pricing breakdown.

This offer cannot be combined with other offers. Valid for new stays only.