Hilton Head Island, SC Luxury Vacation Rentals

Find luxury vacation rentals on Hilton Head Island, SC with real estate agent & realtor, Karen Ryan.

Luxury Vacation Rentals in HILTON HEAD ISLAND

Price

Living Area

7 Donax Road

Active Under Contract

$1,175,000

7 Donax Road, Hilton Head Island, SC 29928

3 Beds 2 Baths 1,642 Sq.Ft.

Lowcountry Regional MLS

326 Spanish Wells Road

$4,200

326 Spanish Wells Road, Hilton Head Island, SC 29926

55 Gardner Drive Unit C1

$3,198

55 Gardner Drive Unit: C1, Hilton Head Island, SC 29926

141 Lamotte Drive Unit Apt F1

$2,650

141 Lamotte Drive Unit: APT F1, Hilton Head Island, SC 29926

55 Gardner Drive Unit B1

$2,587

55 Gardner Drive Unit: B1, Hilton Head Island, SC 29926

42 Forest Beach Drive Unit 3023

$2,300

42 Forest Beach Drive Unit: # 3023, Hilton Head Island, SC 29928

50 Marshland Road Unit Apt 1

$2,300

50 Marshland Road Unit: APT 1, Hilton Head Island, SC 29926

55 Gardner Drive Unit S1

$2,263

55 Gardner Drive Unit: S1, Hilton Head Island, SC 29926

Two-story pale green condominium building with a covered entry and landscaped walkway.

$1,800

8 Old South Court F, Bluffton, SC 29910

2 Beds 2 Baths 1,000 Sq.Ft.

Lowcountry Regional MLS

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Map of Hilton Head Island Luxury Vacation Rentals

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A Guide to Our Area’s Gorgeous Neighborhood

Hilton Head Island

Hilton Head Island

Hilton Head Island Real Estate Blogs

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Hilton Head Island Neighborhood Spotlight: Port Royal Plantation

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Waterfront Properties on Hilton Head Island: What to Look For

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Hilton Head Island Local Event Roundup: Fall 2026

Sandy beach path through dune grass leads to a calm shoreline beneath a bright blue sky.

The Best Hiking and Nature Trails on Hilton Head Island

White Southern-style house with black shutters, brick steps, and a moss-draped oak tree.

Hilton Head Island Neighborhood Spotlight: Hilton Head Plantation

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The Best Live Music Venues on Hilton Head Island

Closed two-panel window overlooks a mature oak, above a built-in seat with a faded blue pillow.

The Hilton Head Bridge Everyone's Been Waiting For Is Not the Bridge That's Getting Built

Bluestone pool terrace and raised spa beside a stucco home, framed by live oaks and pink flowering shrubs.

The HOA Number on a Hilton Head Golf Listing Isn't the Number You'll Actually Pay

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A Guide to Fishing on Hilton Head Island

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Best Activities and Adventures on Hilton Head Island

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Dog-Friendly Things to Do on Hilton Head Island

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Hilton Head Island's Best Coffee Shops and Cafes

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Creative Date Night Ideas on Hilton Head Island

Condo living room with an orange sofa and floor-to-ceiling ocean-view windows.

What to Know About Buying a Second Home on Hilton Head Island

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Comparing Hilton Head’s Gated Communities As A Buyer

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The Best Happy Hour Spots on Hilton Head Island

Condo living room with a white sofa, round coffee table, and tall black-framed windows.

Hilton Head Island Neighborhood Spotlight: Indigo Run

Waterfront building with a lighthouse-style tower overlooking a marina and boats.

How the Hilton Head Island Luxury Market Is Performing in 2026

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The Best Family-Friendly Beaches on Hilton Head Island

Marina lined with yachts and sailboats, leading to a red-and-white striped lighthouse.

What It's Really Like to Retire on Hilton Head Island

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Top Paddleboarding and Kayaking Spots on Hilton Head Island

Spa-like interior with a massage table, tropical plant, and two brown lounge chairs.

Hilton Head Island's Best Yoga Studios and Wellness Spots

Sandy beach with tall dune grass, calm ocean, and a distant beachgoer.

The Best Beaches on Hilton Head Island

Condo living area with a curved gray sofa, open glass door, and pool deck beyond.

Top Real Estate Investment Areas in Hilton Head Island, SC

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The Best Sunrise and Sunset Spots on Hilton Head Island

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Best Home Decor and Furniture Stores in Hilton Head Island, SC

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8 Must-Try Restaurants on Hilton Head Island, SC

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Hilton Head Island Local Event Roundup: Summer 2026

Harbor promenade beside a calm slip, with weathered dock pilings, white clapboard homes, and live oaks.

Inside Wexford: Life In A Hilton Head Marina Community

Condo living room with oak floors and linen sofa opening onto a covered balcony with palms and draping Spanish moss.

Hilton Head Luxury Condo Or Home: Choosing Your Fit

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A Guide to Hilton Head Island's Art Scene and Galleries

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A Local's Guide to Hilton Head Island's Best Brunch Spots

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Best Waterfront Restaurants on Hilton Head Island

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Hilton Head Island Farmers Markets: A Guide for Locals

A striped lighthouse rises above docked yachts in a marina at sunset.

How to Find the Right Neighborhood on Hilton Head Island

Sandy beach path winds through tall dune grass toward the ocean.

What Buyers Need to Know About Gated Communities on Hilton Head

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Selling Your Home on Hilton Head Island: What to Expect

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Hilton Head Island Local Event Roundup: Spring 2026

Condominium exterior with a white-railed staircase, ornate arched entrance, and palm trees.

Hilton Head Island Neighborhood Spotlight: Shipyard

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The RBC Heritage Experience: Hilton Head Island’s Premier Golf Event Is a Must-See

Shorebird in shallow surf beneath an orange sunset over the ocean.

Things to Do on Hilton Head Island, SC

Beachgoers relax beneath blue-and-green striped umbrellas on a sandy shore.

Hilton Head Island Neighborhood Spotlight: Forest Beach

Furnished nook with a wooden storage bench, pillows, teal paneled walls, and a window.

How to Use Color Psychology to Transform Your Hilton Head Island Home

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Exploring The Golf Scene On Hilton Head Island

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Waterfront Bliss: What to Look for When Buying a Waterfront Home on Hilton Head Island

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Discovering Hilton Head Island by Bike

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The Ultimate Guide to Hosting the Perfect Dinner Party in Your Hilton Head Island Home

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Why Karen Ryan Is the Right Partner for Your Hilton Head Home Journey

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Hilton Head Island Local Event Roundup: Upcoming Events in Late Summer/Early Fall 2024

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Why Hilton Head Island is the Best Place to Live

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Hilton Head Island Local Event Roundup: Upcoming Events for Spring 2025

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Hilton Head Island: Notable Amenities That Make Every Day Feel Like a Vacation

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Top Landscaping Tips to Beautify Your Hilton Head Island Home

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How to Prepare Your Hilton Head Island Luxury Home for a High-Value Sale

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Hilton Head Island Local Event Roundup: Summer 2025 Edition

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Creating a Culinary Masterpiece: 8 Ideas for Upgrading Your Hilton Head Island Kitchen

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Hilton Head Island Local Event Roundup

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Living on Hilton Head Island, SC

Coastal residences with balconies behind tall beach dune grass in warm evening light.

How to Own Your Dream Home on Hilton Head Island: A Step-by-Step Guide

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Buying a Luxury Home in Hilton Head

Waterfront condos with striped awnings, wooden decks, and boats docked along the marina.

Hilton Head Island Neighborhood Spotlight: Sea Pines

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Popular Wildlife on Hilton Head Island

Colorful kayaks float together on the water beside a person in a blue life vest.

The Perfect Hilton Head Island Weekend Itinerary

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Hilton Head Island Neighborhood Spotlight: Wexford

Staged living room with a cream sofa, colorful patterned rug, and bright windows.

Buying a Home on Hilton Head Island, SC: What to Look For

Let's Work Together

Whether buying or selling a home, Karen offers the highest level of care and expertise. If you’re looking to make a real estate move, please reach out. She’d love to be a resource for you.

Let’s Connect

Contact Details

Karen Ryan

Phone

(843) 422-1101

Email

[email protected]

Address

1038 William Hilton Pkwy Hilton Head Island SC 29928

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