Vacation rentals with a kayak in Hilton Head Island

Find and book unique kayak rentals on Airbnb

Quick stats about vacation rentals with a kayak in Hilton Head Island

  • Total vacation rentals

    Explore 60 vacation rentals in Hilton Head Island

  • Nightly prices starting at

    Hilton Head Island vacation rentals start at G$25,051 GYD per night before taxes and fees

  • Verified guest reviews

    Over 940 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

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 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

Top-rated kayak rentals in Hilton Head Island

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
Condo in Palmetto Dunes
4.92 out of 5 average rating, 109 reviews

Coastal Breeze Top Floor Retreat #26148

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 Sea Pines
5 out of 5 average rating, 16 reviews

Marriott Harbour Club - 2BD

Enjoy waterfront vacations at Hilton Head's Sea Pines. Overlooking scenic Calibogue Sound on the southern end of Hilton Head Island lies Marriott's Harbour Club, one of three Marriott Vacation Club resorts within Hilton Head's Sea Pines Resort. Hilton Head Island is known for its charm, hospitality and natural beauty. It is also an island of activity, including championship golf courses and hundreds of tennis courts. Marriott's Harbour Club puts you amid everything the island has to offer.

Top guest favorite
Home in Daufuskie Island
5 out of 5 average rating, 11 reviews

Historic Home With Water Views

The Historic Sarah Hudson Grant House- A traditional Lowcountry style, Gullah Geechee cottage located on Daufuskie Island. This historic 1890’s cottage was originally home to the island’s midwife. Waterfront with sprawling marsh views as far as the eye can see. Watch boats on the intracoastal waterway, and experience the island’s most stunning sunsets. Serene and peaceful setting, the yard features giant ancient trees dripping with Spanish moss, and over 30 native palms trees.

Top guest favorite
From the balcony, a panoramic view of the heated outdoor pool is visible, surrounded by lounge chairs. The backdrop features lush palm trees and the serene coastline. Beyond, the tennis courts and the nearby boardwalk meander through marshlands, leading to the tranquil beach at sunset.
Condo in Palmetto Dunes
4.97 out of 5 average rating, 127 reviews

Gorgeous 2 Bedroom Condo - Pool/Tiki Bar/ Beach

Welcome to your Gorgeous Beachside Condo! Come stay at our beautiful coastal condo at the Gated Hilton Head Resort. Your 2 Bedroom, 2 Bath Villa sleeps up to 6 people. Located Mid-Island; close to EVERYTHING! *2 Outdoor Pools *1 Heated Indoor Pool *Hot Tub *Sauna *6 Tennis Courts *Fitness Center *Badminton Court *Volleyball *Picnic Area *Poolside Deli *Cabana Bar *Boardwalk to the Beach *Coco's Bar & Grill *Elevators *On-site Shop, Bike Rentals, & Laundry *Free Parking

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, 84 reviews

This Is An Oceanfront Luxury 2BR/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! Beach Toys! Large, family-size beach tent, 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, 25 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
Apartment in Hilton Head Island
New place to stay

Bluewater Resort & Marina - Spacious 3BR/3BA

Come delight in the beauty of the Intracoastal Waterway and savor stunning sunsets from the dock at Bluewater Resort & Marina located on Skull Creek. Bring your boat for free dockage or just relax and watch the boats and yachts go by. This resort has something for everyone, from water and nature lovers to golfers and loungers. This is also a great resort to enjoy the beauty of HHI without the crowds common to other areas of the island.

Guest favorite
Condo in Palmetto Dunes
5 out of 5 average rating, 14 reviews

Oceanfront Villamare| Pools | Fitness | Firepit

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
Condo in Hilton Head Island
4.92 out of 5 average rating, 13 reviews

Tennis - King Bed - 3 Pools - Beach

Our Villa features 2 bedrooms and 2 bathrooms, coastal furnishings, luxury linens, and smart TVs. We are on the third floor (no elevator) and overlook the tennis courts and the indoor pool area. It is only a 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 6 available.

Superhost
The shared outdoor pool area is surrounded by palm trees and well-maintained landscaping. Loungers are placed on the pool deck, inviting relaxation by the sparkling water. The pool features steps leading into the shallow end, and the layout provides ample space for guests.
Townhouse in Hilton Head Island
4.85 out of 5 average rating, 247 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
4.96 out of 5 average rating, 54 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
4.72 out of 5 average rating, 143 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$79,327 GYDG$79,327 GYDG$79,327 GYDG$79,327 GYDG$79,327 GYDG$73,064 GYDG$64,088 GYDG$63,253 GYDG$60,121 GYDG$57,199 GYDG$75,987 GYDG$68,680 GYD
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