Vacation rentals with a kayak in Hilton Head Island

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Top-rated kayak rentals in Hilton Head Island

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Guest favorite

A cozy sleeping area features a custom twin loft bed above a queen-sized bed, complemented by soft linens and decorative pillows. Natural light enters through the window, softened by light curtains, while a ladder offers access to the loft. A chair is positioned in the corner.

Condo in Hilton Head Island

4.9 out of 5 average rating, 94 reviews

Coastal Breeze -Top Floor - Hilton Head Island

2BR/2BA-Top Floor- Corner Villa -Direct Beach Access-2 Outdoor Pools-Heated Indoor Pool &Hot Tub-Master Bedroom-1 King Bed,Guest Custom Twin loft over Queen + Foldout 4" Twin Mat. Private patio, Smart TVs, dining for 6, fully equipped kitchen, Drip & Keurig coffee maker, blender + separate water to fill water bottles, Wi-Fi, bath towels & bed linens provided. Extra USB plugs in guest bedroom for all your electronic needs. Beach supplies: beach wagon, beach chairs, paddle ball, boogie boards.

Guest favorite

Aerial view of Marriott's Harbour Club reveals the spacious resort surrounded by lush greenery and tall trees. Scenic Calibogue Sound is visible in the background, with the iconic Harbour Town Lighthouse further enhancing the inviting landscape.

Condo in Hilton Head Island

5 out of 5 average rating, 8 reviews

Marriott Harbour Club - 2BD

Nestled in Hilton Head Island's Sea Pines Resort, Marriott's Harbour Club overlooks scenic Calibogue Sound. This Marriott Vacation Club resort offers access to Hilton Head's natural beauty, hospitality, and activities, including championship golf courses and numerous tennis courts. Enjoy fine dining, shopping, yacht harbors, galleries, Harbour Town, horseback tours, ecotours, watersports, and museums. Marriott's Harbour Club provides an ideal seaside getaway with family-friendly activities.

Superhost

A spacious outdoor lounge area features comfortable seating with soft cushions, surrounded by palms. Blue drapes flow gracefully, providing shade. Several lounge chairs line the deck, with an inviting view of the beach and nearby swimming pool.

Apartment in Hilton Head Island

New place to stay

Marriott's SurfWatch. 3 Bedroom/ 3 Bath Villa

Located on the scenic shores of Hilton Head Island, Marriott’s SurfWatch offers a coastal retreat that blends beachfront tranquility with resort-style convenience. Surrounded by salt marshes and palmetto trees, the resort features direct beach access, indoor and outdoor pools, a fitness center, walking trails, and a seasonal oceanfront bar and grill. Families will find the picnic and grilling, fire pit, game room, and activities designed to make your stay as relaxing or active as you like.

A wooden outdoor table with several chairs is set on the lawn, overlooking a private dock extending into the water. Lush greenery is visible nearby, and clear skies provide a serene backdrop to the tranquil waterfront setting.

Home in Saint Helena Island

4.8 out of 5 average rating, 44 reviews

Waterfront Paradise in the heart of the Lowcountry

Lovely home on the water near Beaufort, SC. This 4 bed, 3 bath home on an almost 1/2 acre lot is in the heart of the Lowcountry. It has unobstructed sunset views and private dock. This is the prime location for summer fun - fishing, boating, beaching, cooking out, and living slowly. It's just 20 minutes from down town Beaufort and 20 minutes from Fripp Island. The house is situated on Port Royal Sound, across the water from Paris Island and Hilton Head. It's truly a boaters paradise!

Guest favorite

A serene outdoor space featuring a private pool surrounded by lush greenery. The inviting pool is complemented by a spacious deck, and the home in the background has large windows and access to the outdoor area. Sunlight filters through the trees, creating a peaceful ambiance.

Home in Hilton Head Island

5 out of 5 average rating, 8 reviews

26 Port Tack | Dog Friendly | Pool | Lagoon View

PROPERTY AMENITIES Free Wi-fi Smart TV’s | DVD Keyless Entry Keurig Washer & Dryer (in-unit) Pool and Spa Game Room PROPERTY CONFIGURATION 4 Bedrooms 2 Bathrooms Sleeps 10 1 King | 3 Queen | 1 Twin | 1 Sleeper Sofa Max Parking of 6 Vehicles BEACH ACCESS Parking for the beach is located at the Dunes House or a walk/bike ride to the beach is a half mile from Port Tack to Mooring Buoy. PROPERTY REMINDERS 4-night min stay required Pool/spa heated (add'l fee) Dog Friendly (add'l fee)

Guest favorite

A balcony view showcases lush greenery leading to the beach. The ocean is visible in the distance, with beach access paths winding through the area. Picnic tables are positioned on the grassy expanse, providing outdoor seating options under the warm sun.

Condo in Hilton Head Island

4.89 out of 5 average rating, 56 reviews

ThisISOceanfront30%OffJulyDates2BR/2BACondo

Enjoy breakfast, peace and luxury at this large oceanfront 2BR/2BA condo. While the whole family relaxes, see and hear the waves crashing on Hilton Head. Enjoy this ocean view and sound all day or enjoy the many amenities! 2 bikes, Beach Toys! Large, family-size beach tent, umbrella, blanket, beach chairs, towels for 8, beach cart for the short 200 steps to private beach access. Private oceanfront sundeck. Pool. All provided at no extra charge! Yes!Free Beach Toys, too!

Top guest favorite

An outdoor living space features a round table surrounded by five mint-colored chairs under a large blue umbrella. A gas grill is positioned nearby on a wooden deck, with additional seating provided by a light blue Adirondack chair.

Townhouse in Hilton Head Island

4.96 out of 5 average rating, 25 reviews

Walk to Beach: Hilton Head Island Resort Gem

Sunshine and sea breezes await at this Hilton Head Island vacation rental! Located in the Palmetto Dunes Oceanfront Resort, the 2-bed, 2-bath townhome features a bright interior with a full kitchen, a furnished deck for afternoon cookouts, and access to perks like an outdoor pool, sports courts, and restaurants. Ready to explore? Enjoy a picnic at the private beach, tee off at the on-site golf course, or visit the Coastal Discovery Museum. Book now!

Guest favorite

Two kayaks are positioned on the grassy edge of a serene lagoon, featuring vibrant orange and blue colors. A wooden dock extends into the water, framed by lush trees and a clear sky, inviting exploration and relaxation in the tranquil surroundings.

Townhouse in Hilton Head Island

5 out of 5 average rating, 8 reviews

MyStay at 7649 Huntington - Lagoon Views & Beach!

Escape to 7649 Huntington Villa—your perfect Hilton Head retreat! This stylish 3BR/3.5BA villa in Palmetto Dunes offers lagoon views, a short walk to an uncrowded beach, and access to a heated pool, hot tub, and more. Enjoy a fully stocked kitchen, comfy living space, and beach gear ready to go. Golf, bike trails, and waterfront dining are all nearby, plus a free resort shuttle. Book now and unlock your dream vacation—because you hold the key!

Superhost

The living area is designed with a comfortable blue sofa and accented by light wood furniture. A flat-screen TV is positioned for viewing, and a sliding door opens to a balcony with views of the exterior. Soft lighting pairs with artwork on the walls.

Condo in Hilton Head Island

New place to stay

Luxe Coastal Beach Villa - King Bed - 3 Pools

Our newly renovated Villa features two bedrooms and two bathrooms, all new furnishings, luxury linens, smart TVs and charging stations. We are on the third floor (no elevator) and overlook the tennis courts and the indoor pool area. It is only a leisurely, 7 min walk through the shaded lagoon area, past the two outdoor pools to the natural sandy beach! Our unit is ideal for two couples or a small family. We have sleeping for 8 available.

Guest favorite

A wooden balcony table is set with glasses of water and a bottle of chilled champagne, accompanied by a platter of fresh grapes and cookies. The oceanfront view showcases sandy beaches, pool areas, and palm trees under a clear blue sky.

Condo in Hilton Head Island

5 out of 5 average rating, 6 reviews

Beachfront, Fitness Center, Pools

SNOWBIRD FRIENDLY Here at Beach House Boutique Vacation Rentals we believe in providing you with amenities you won't find anywhere else. See all this 2bedroom/2bathroom Oceanfront Villa has to offer! 1. Luxury bedding, Bath & Beach Towels 2.. Hair dryers in each bathroom 3. Both a KEURIG and Regular Coffeemaker 4. Gift bag with local treats 5. Beach Towels for guest use 6. Keyless Entry 7. Oceanfront 8. Ocean Views

Guest favorite

A sunlit outdoor pool area features clear water surrounded by lounge chairs. Lush palm trees and manicured hedges frame the pool, while multi-story buildings provide a backdrop. Umbrellas offer shaded seating options, creating a relaxing environment for guests to enjoy.

Townhouse in Hilton Head Island

4.86 out of 5 average rating, 236 reviews

Coastal 2Bdrm Stay | Pool Access, Walk to Beach

Experience Hilton Head at our cozy coastal townhouse, steps from the beach! Enjoy a shared outdoor pool, private patio with grill, and a fully equipped kitchen. Family- and pet-friendly with Pack N Play, dedicated workspace, high-speed WiFi, washer & dryer. Relax, unwind and make great memories. 2 bedrooms, 3 bathroom, perfect for your getaway!

Guest favorite

A spacious living room features a comfortable sectional sofa and a glass coffee table. Large windows provide a view of the ocean and patio, while a flat-screen TV is mounted on the wall. A ceiling fan and coastal decor create a relaxed ambiance.

Condo in Hilton Head Island

5 out of 5 average rating, 39 reviews

Palmetto Dunes Luxury Oceanfront Gem w/ View -King

Welcome to 451 Captain’s Walk in Palmetto Dunes Resort! A Premier Hilton Head Island Oceanfront Location. Centrally located to everything on the Island. This beautiful oceanfront villa is just steps away from the beach. Walk in and be immediately welcomed by the ocean. Condo is on 4th of 5 floors with Elevator.