Villa holiday rentals in Dataw 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

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 & pool. Enjoy beach bar, sports bar, tennis/pickle ball courts, fitness room & bike rentals. Equipped with full kitchen, queen bed, futon sofa. Ideally suited for 2 adults. Starter set of toiletries/towels provided. Laundry room on-site. Located close to all the fun the island has in store for you! *Additional cleaning fees for monthly stays. Short Term Rental Permit # 022967

Pool + Ocean View + Walk to Beach | Captain Villa

Welcome to 326 Captain John Fripp Villa—a breezy ocean-view getaway just steps from the sand and a pool. With fiber Wi-Fi, coastal charm, and room for six, this villa combines comfort, convenience, and unbeatable island access. 🌴 Prime location - walk to beach & private pool 📺 Massive 70" smart TV for cozy movie nights 💻 Fiber optic WiFi - ideal for remote work & streaming 🎨 Freshly updated with new paint, flooring & furniture 🛏️ 2 bedrooms, 2 bathrooms - perfect for families or couples.

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.

3bd/2ba Pet Friendly, 3 pools, pickleball!

a beautifully renovated 3BR/2BA villa tucked away in the highly sought after Ocean Ridge Resort community of Edisto Beach. Guests will have access to the resort amenities which include 3 pools (one which is heated), a putt putt course, a playground, 2 tennis courts, 4 pickleball courts, a fitness center, and more! Another guest favorite feature of this home is the colorfully lit, screened-in tiki bar, perfect for hanging out and enjoying a beverage after a long day at the beach.

Spacious dog-friendly villa, walk to the beach

Welcome to 640 Queens Grant, your perfect family getaway on Hilton Head Island! This vibrant 3BR, 2.5BA luxurious villa is professionally decorated, accented with inviting, colorful coastal decor throughout. The villa offers a fully-remodeled kitchen, a spacious and comfortable living area with plenty of ways to relax and unwind. Outside, there is a large, private patio with a gas grill, an outdoor dining set and fast access to five community swimming pools and the beach.

Fripp Villa-Golf Cart Included-Club Cards +

328 John Fripp Villa - Golf Cart Included/Club Cards Available. Tidal Treasure is beautiful 2 bedroom, 2 bath rental. A golf cart is included with your stay. Sleeps 6. It offers an open living and dining room area with an outdoor patio. The master bedroom porch peeks out at the pool area and into the eyes of wildlife. Just beyond our backdoor is a beautiful grassy courtyard and a two hundred yard walk straight to one of the most beautiful beaches in the Carolinas.

Downtown Port Royal/min to Sands Beach/Parris Isla

Located in Historic, Peaceful Port Royal.. This home is just a short walk to a small beach and boardwalk, a short walk to the Shadow Moss Trail-17 miles of walking and biking path, as well as fabulous restaurants and quaint shops. just a short drive to downtown Beaufort(5 miles), harbor Island, Hunting Island(major Beach) and 2 miles to Parris Island. This home is a 2 bedroom 2.5 bathrooms. All bedrooms are located upstairs with their own on-suite.

The Fripp Flopp

Beautiful location on the back waters and canal of Fripp Island, SC, only 0.2 miles from the beach. Centrally located on the island with easy access to bike trails and short golf cart rides to anywhere on the island. The sunset and marsh views from this Tennis Villa are unforgettable and what puts this location on the map! This is our second home and our little piece of paradise that we’d like to share with those who will treat it as we do.

Beach Relax in Palmetto Dunes Families-Golf-Tennis

Beach & Golf: 7 min stroll to the beach views of the Golf course. Hickory Cove villa 2 Bedrooms + Loft, 3 Baths, (Sleeps 6-8) Beautiful Villa on the 18th tee of the Robert Trent Jones Golf Course in Palmetto Dunes. This Villa is perfect for golfers, families and short term home office. Everything is less than 10 min walk: The Beach Robert Trent Jones golf course Palmetto Dunes Tennis Center The General Store The Dunes House

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!

Lg. 2BR|2.5BA Direct Oceanfront Community - 5 Star

Set within Island Club’s beachfront community on Folly Field Beach, this updated 2BR|2.5BA villa is a two-minute walk to the sand via private resort paths—no streets to cross. The largest Island Club two-bedroom floor plan offers 1,300+ sq ft, sleeping up to 6 in bedrooms plus a sleeper sofa, with seasonal pools, hot tubs, beach gear, fitness room, and more.