Hilton Head Island Vacation Rentals

Wake up to paradise
every single morning.

45 hand-selected Hilton Head vacation rentals — your own slice of paradise along the coast, managed with the comfort and care of a family business.

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5-Star Stays
Rated 5 stars by guests again and again.
Beach Ready
Beach chairs, towels & carts in every home.
Exclusive Perks
Special discounts on bike rentals & local activities.
Locally Owned
24/7 guest support you can count on.
Find Your Stay

Every kind of Hilton Head vacation rentals.

From oceanfront villas for two to sprawling homes for the whole family — and yes, your dog is welcome.

Condos & Villas – Hilton Head Vacation Rentals

Condos & Villas

Thoughtfully furnished, steps from the beach. Perfect for Couples & Small Groups.
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Private Homes – Hilton Head Vacation Rentals

Private Homes

Space to spread out, room for everyone. Essential for Families & Large Groups.
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Pet-Friendly – Hilton Head Vacation Rentals

Pet-Friendly

Four-legged guests welcome. Because the best vacations include the whole pack.
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Featured Properties

Guest favorites, hand-picked.

Pet Friendly Walk to the Beach - 2 bed 2 bath flat
Condominium

Pet Friendly Walk to the Beach – 2 bed 2 bath flat

  • 2
  • 2
  • 6
from $195 / night
Walk to Beach - Pet Friendly Poolside 2BR Villa
Condominium

Walk to Beach – Pet Friendly Poolside 2BR Villa

  • 2
  • 2.5
  • 6
from $165 / night
Coastal Villa w/ Screened-in Porch & Walk to Beach
Condominium

Coastal Villa w/ Screened-in Porch & Walk to Beach

  • 3
  • 3
  • 6
from $195 / night
Walk to Beach - Family-Friendly Condo w/ Cabana, Pool, Beach Gear – Hilton Head
Condominium

Walk to Beach – Family-Friendly Condo w/ Cabana, Pool, Beach Gear – Hilton Head

  • 2
  • 2
  • 6
from $145 / night
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Our Story
Our Story

Family owned.
Island raised.

HH Island Rentals was built by people who live here and work here, managing Hilton Head vacation rentals with the same care we’d want for our own home. We care deeply about every guest experience, so when you stay with us, you get more than a clean key — you get a local team invested in your trip from first inquiry to checkout.

Meet the Team
Guest Reviews

They keep coming back.

★★★★★

Great location, clean, awesome response time from Owner. The entire unit is well updated and very nice, the WiFi is fast enough to stream Netflix, and all appliances worked great. Rob is very accommodating and responsive. We'll definitely stay here again when we return to Hilton Head!

Norbert
★★★★★

The condo was beautifully designed and our family had everything we needed for a weekend trip. I really loved that everything felt so new and it was really clean; almost like we were staying at a hotel but with the conveniences of a kitchen to cook at home. The location was really convenient for walking and getting around. Thanks so much for a wonderful vacation getaway.

Laura
★★★★★

The condo is perfect with comfortable beds, lots of kitchen utensils and pots, TV's, grill and so much more. Don't hesitate to book with Rob. He is a competent and very caring host who is easy to communicate with and is ready to ensure you have a most delightful vacation! We plan on booking this unit again.

George
★★★★★

Our stay at the Sea Crest was great. The location is awesome as it is beach front and near many restaurants and shops. The room itself was set up nicely and perfect for our 4 person family. Pool bar Jim’s is on location and a great place to get casual food and drinks for the beach. Pools at the place were fine.

Mark
★★★★★

When I found this condo online, I thought it was too good to be true. I reserved it and when we showed up, it was just as described. The amenities were included. It was very clean. I would highly recommend Rob and this rental.

Jennifer
★★★★★

Rob was very responsive of our needs. Great location. Very clean and well represented on the website. We would consider this property again when visiting Hilton Head.

David
Your Hilton Head Getaway

Ready to find your perfect stay?

Browse our full collection of homes and villas, or reach out — we’ll help you find exactly the right fit.

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Hilton Head Island Insights

From Island Insights

Local tips, guides, and trip inspiration from your Hilton Head hosts.

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