Villa holiday rentals in Hilton Head Island

New Listing! Penthouse Oceanfront Sea Cloisters Co

Relax and enjoy the best of Hilton Head from this oceanfront 3BR/3BA penthouse at Sea Cloisters. Located mid-island off Folly Field Road, this bright and spacious condo offers breathtaking ocean views, a fully stocked kitchen, and easy beach access just steps away. With two king bedrooms on the main level and a loft with one queen bed and one full bed, there’s plenty of room for families or groups of friends (sleeps 6 total). Enjoy the direct ocean view from the master bedroom, unwind in the co

Walk to Beach | Lagoon View | 2 Kings+Queen & Bunk

On Island Time is a beautifully renovated Lowcountry beach villa, perfect for relaxed family vacations. Walk to the beach, Lowcountry Celebration Park, shops, dining, and pickleball. Bright open main level with spacious living area, smart TV, lagoon-view balcony, fully equipped kitchen, dining for 8, half bath & washer/dryer. Three private bedrooms each with ensuite bath: two king masters and a third with queen + twin bunks. Sleeps 8. High-speed WiFi, keyless entry, pool access, and beach gear.

Beach Awaits You! Weekly Discounts!

Located at the gated, ocean front Hilton Head Beach & Tennis Resort, this cozy condo is only a 4 minute walk to beach and pool. Enjoy the beach bar, sports bar, tennis/pickle ball courts, fitness room & bike rentals. Equipped with full kitchen, queen bed, futon sofa. Ideally suited for two adults (max occupancy 3). Starter set of toiletries/towels provided. Laundry room on-site. Resort is located close to all the fun the island has in store for you! *Additional cleaning fees for monthly stays.

Prime Waterview! Hilton Head Shelter Cove Marina

Permit 073816 Enjoy easy access to everything Hilton Head has to offer from this centrally located Condo in the heart of Shelter Cove Marina. Not only will you have breathtaking views of the sunset and the marina right from your balcony, but you also have many amenities right at your doorstep! Shelter Cove is one of the main attractions on Hilton Head Island with many shops, restaurants, weekly entertainment and water sports. You also have access to the private Palmetto Dunes Beach community.

Walk to the Beach, One Level Villa, COMFY beds

5-10 minute walk to the pristine Hilton Head beach, retreat to your spacious villa in Queen's Grant of Palmetto Dunes. With nearly 1500sq ft and lofted ceilings, you can spread out comfortably. New living room furniture that all reclines, amazing king green tea memory foam mattress in both bedrooms, and a fully stocked kitchen (blender, toaster oven, crock pot+.) The master and living room open up to a private back patio equipped with a grill, dining room table and beach accessories.

Oceanfront Scandi Oasis Amazing View & Heated Pool

Villa Aalto is a new Scandinavian style oceanfront oasis created for ease and relaxation throughout your beach vacation. The streamlined interior offers high-end finishes and luxurious hotel-like amenities, with a fully functional kitchen and serene living area overlooking the ocean. The year-round heated pool and private path to the beach make for stress-free days, but the close proximity to Coligny allows you to bike to restaurants, playgrounds and shops within minutes as well.

1872 Beachside Tennis, Sea Pines: Beachfront Villa

Surrounded by lush vegetation on Hilton Head Island, this cozy residence features a superb blend of sun and shade. From the tiled terrace, steps lead into the turquoise pool. The heart of the village is a brief bike ride away. Discover waterfront restaurants, unique shops, and activities for the whole family. A 5-minute stroll is all it takes to sink your toes into the toasted sand at the beach. Copyright © Luxury Retreats. All rights reserved. STR Permit Number: 077170

Walk to Beach, Indoor Pool, King Bed, Hot Tub!

Why you’ll love this space: Fully renovated with high‑end appliances Indoor heated pool & hot tub Outdoor pool, renovated 2025 (Open April 1 - October 31) Tennis - & pickleball courts Approx 5 minute walk to beach; 10 minute walk to Coligny 320 Mbps Wi‑Fi with dedicated workspace Chef’s kitchen, washer/dryer, cypress ceilings Marble walk‑in showers & electric fireplaces Beach gear included (towels, chairs, wagon, toys) STR Permit No. 040546

💎Direct Oceanfront Villa - Heated Pool Ocean View

Welcome to the Ocean Gem! Relax and listen to the crashing waves on your private balcony of our newly renovated, newly furnished, direct oceanfront, one bedroom, one bathroom, beautiful beach villa. Ocean Gem is located in Ocean Dunes complex, a private gated community, on South Forest Beach and only steps from the popular Coligny Plaza. You will enjoy the wonderful accommodations, heated pool, picnic area and spectacular views! Thank you

HHI South Forest beach/WLK TO BEACH, dining, pool

Pack up the whole crew—two-legged or four—and escape to this fully furnished, perfectly located cozy condo in Hilton Head’s popular Treetops complex. Enjoy three refreshing pools, tennis courts, and a laid-back vibe perfect for relaxing or playing. Just a 10-minute walk to the beach and steps from Coligny Plaza, you’ll be close to shopping, dining, and all the island fun. It’s your ideal home base for sun, sand, and good times!

38 Hickory Cove

Welcome to our luxury 3 bed/ 3.5 bath villa, nestled in the shady Hickory Cove Community inside of Palmetto Dunes! Take a 5 minute stroll to the private community beach, and after a long day in the sun, take a dip in the community pool located just steps from your back deck! This property was totally renovated in 2024 with brand new bathrooms, kitchen, flooring, paint, and more! It's the perfect home away from home!

Escape at Seascape Villas, quiet beach getaway

Escape at Seascape! Secluded, three level villa provides a tranquil retreat. 3rd floor master suite for added privacy. Included beach cart and beach equipment makes a short walk to the beach convenient. Private, locked beach cabana with bathroom for Seascape guests. Close to Coligny plaza for shopping and dining. Natural lagoon setting gets you close to nature. Patio with gas grill. Two pools to unwind and relax.