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

The living area presents a light and airy ambiance with soft blue walls and natural light streaming through sliding glass doors. A comfortable dark sofa and patterned armchair are arranged around a coffee table, complemented by a decorative area rug and tasteful wall art.

Condo in Hilton Head Island

4.83 out of 5 average rating, 72 reviews

Panoramic Water View Overlooking Shelter Cove !

Beautiful one bedroom villa in Shelter Cove - panoramic deep water views. Remodeled and in the classic low country style, condo includes: updated kitchen, new cabinets and granite counter tops, new flooring and fresh paint. The ultimate location, walk to shopping and dining, free trolley service will pick up and drop you off in Palmetto Dunes with private beach access. Enjoy incredible and soothing views, the wide blue water views will overwhelm you. Let this be your "home away from home."

Guest favorite

Condo in Hilton Head Island

4.9 out of 5 average rating, 77 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.

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

4.85 out of 5 average rating, 40 reviews

Oceanfront 20%Earlyor30% Weekly Discounts 2BR/BA

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/pickleball/tennis. All provided at no extra charge! Yes!Free Beach Toys, too!

A white, single-story home is surrounded by lush green grass and trees. Large windows adorned with plants offer views of the outdoors, while the sloped roof enhances the structure's character. The space conveys a sense of openness and connection to nature.

Home in Saint Helena Island

4.78 out of 5 average rating, 40 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

Home in Hilton Head Island

4.95 out of 5 average rating, 125 reviews

Ocean-View Treetop Escape w/ Fire Pit!

Plan your next getaway for a stay on the sandy shores of Hilton Head Island when you book this 2-bedroom, 2-bathroom vacation rental home. The treetop house features a private setting with gorgeous ocean views that can be seen from inside and outside of the property. Sway in the hammock with a good read or dine al fresco on the patio or deck. When you’re ready to explore the island, take a ride to see the Harbour Town Lighthouse or book a tee time at Harbour Town Golf Links.

Guest favorite

A shared outdoor pool area is highlighted, featuring a large swimming pool surrounded by sun loungers and a shaded seating area. A green umbrella provides cover over a round table, while trees line the backdrop, creating a relaxing environment.

Townhouse in Hilton Head Island

4.86 out of 5 average rating, 225 reviews

Coastal 2BR Stay | Pool Access, Walk to Beach

Experience the delight of Hilton Head at our cozy coastal townhouse, just steps from the stunning beaches! Enjoy the shared outdoor pool and a private patio with dining and grill. The townhouse is fully equipped for your comfort and convenience, allowing you to relax and make fun and amazing memories! *Family-friendly (Graco Pack N Play included) *Pet-friendly *Dedicated workspace + highspeed wifi *Washer & dryer *Full kitchen *Relax in the shared pool *Walk to the beach

Apartment in Hilton Head Island

5 out of 5 average rating, 3 reviews

LUXURY BEACHFRONT BARONY CLUB RESORT+AMENITIES

Create a lifetime of memories at this premium family-friendly beachfront getaway. Enjoy several beachfront pools, waterslide pools, fitness center, top of the line amenities Additional $500-$1000 SAVINGS available with 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 on certain 7-Night stays. All reservations require a FRI-FRI, SAT-SAT OR SUN-SUN STAY 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 may be able to provide shorter stays however, stays shorter than 7-Nights *may incur a higher nightly rate

Superhost

A sunlit sunroom features large windows allowing natural light to fill the space, showcasing a comfortable seating area with two chairs and a woven rug. A decorative shelf holds colorful beach towels, while wooden accents and coastal decor create a relaxing atmosphere.

Townhouse in Hilton Head Island

New place to stay

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

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.

Villa in Hilton Head Island

5 out of 5 average rating, 3 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

A view of two golf courses and lagoons stretches across the landscape, showcasing well-maintained green spaces and sandy traps. Palm trees are positioned throughout, and blue skies with scattered clouds provide a bright backdrop.

Condo in Hilton Head Island

4.71 out of 5 average rating, 14 reviews

Sea Pines Plantation Villa-Pet Friendly

Awesome view of two golf courses and lagoons-near the beach with access to a fabulous beach club and a beautiful new Club house with dining facilities. A pool on site and 5 bicycles for your use. My place is good for couples, business travelers, families (with kids), and furry friends (pets). ***Saturday (Check-in) to Saturday (Check-out) 7 night only, during Summer months. Please ask me for details.