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 Palmetto Dunes
4.91 out of 5 average rating, 95 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.

Superhost
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 Sea Pines
5 out of 5 average rating, 9 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

Marriott' 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.

Superhost
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
4.79 out of 5 average rating, 48 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 wooden deck extends towards the water, offering seating under a blue and white striped umbrella. Lush greenery and coastal grass are visible on either side, with calming views of the water in the distance framed by clear blue skies.
Home in Sea Pines
4.96 out of 5 average rating, 141 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 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
4.9 out of 5 average rating, 68 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
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 Palmetto Dunes
5 out of 5 average rating, 15 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!

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 Palmetto Dunes
5 out of 5 average rating, 9 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

Superhost
Apartment in Hilton Head Island
New place to stay

2pm Late Checkout-King Bed-1st Floor - Indoor Pool

OCT 2025 - FEB 2026 Late Checkout 2PM. Relax with the whole family at this peaceful place to stay. This Villa is has two- bedrooms, each with a private bath. - King Bedroom (sleeps 2) - Set of Queen Bunks (sleeps 4) This Beachfront complex has two outdoor pools as well as a year round indoor pool. It is only a short 2 min walk past the beachside pool and shady lagoon area to reach the private, natural beach.

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, 240 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 Palmetto Dunes
4.98 out of 5 average rating, 46 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.

Guest favorite
The charming exterior of the home showcases a spacious front porch adorned with decorative plants and a welcoming entry. Lush greenery surrounds the property, complemented by a manicured lawn and a pathway leading to the front steps, enhancing the inviting appearance.
Home in Hilton Head Island
4.71 out of 5 average rating, 137 reviews

Hilton Head Home

Beautiful home with fenced yard, pool, tiki bar, hot tub, and pool table located in quiet neighborhood. Dock access to fish off or put your kayak in. Boat launch just 2 miles away. Numerous beaches within a 5 minute drive and located just 5 miles from the Tanger Outlets. Its a great house for a family get away!!

Popular amenities for Hilton Head Island kayak rentals

When is the best time to visit Hilton Head Island?

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Avg. priceG$77,462 GYDG$79,556 GYDG$79,556 GYDG$79,556 GYDG$79,556 GYDG$73,275 GYDG$79,556 GYDG$79,556 GYDG$78,300 GYDG$78,300 GYDG$77,462 GYDG$79,556 GYD
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Quick stats about vacation rentals with a kayak in Hilton Head Island

  • Total vacation rentals

    Explore 50 vacation rentals in Hilton Head Island

  • Nightly prices starting at

    Hilton Head Island vacation rentals start at G$23,029 GYD per night before taxes and fees

  • Verified guest reviews

    Over 950 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Hilton Head Island vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Hilton Head Island rentals

  • 4.7 Average rating

    Hilton Head Island stays receive an average rating of 4.7 out of 5 from guests

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