Vacation rentals with a kayak in Hilton Head Island

4.92 out of 5 average rating, 114 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.

ValueOutdoor spacesPool

5.0 out of 5 average rating, 18 reviews

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

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.

LocationHospitalityBiking

5.0 out of 5 average rating, 13 reviews

Home in Daufuskie Island

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.

LocationOutdoor spacesNearby

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.

4.97 out of 5 average rating, 129 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

Outdoor spacesValueCheck-in

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.

4.89 out of 5 average rating, 85 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!

ValueOutdoor spacesCleanliness

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.

4.68 out of 5 average rating, 22 reviews

Tennis - King Bed - 3 Pools - Beach

Our newly renovated Villa features 2 bedrooms and 2 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 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. Rental Permit #075534

LocationOutdoor spacesBeach

Superhost

The dining area features a wooden table that accommodates six, surrounded by white chairs. A modern kitchen is visible, showcasing blue cabinetry and stainless steel appliances, including a stackable washer/dryer. Two pendant lights hang above the table, enhancing the inviting atmosphere.

4.89 out of 5 average rating, 61 reviews

Queens Grant Gem - Updated Condo - Dog - King Bed

Queens Grant #620 - In Palmetto Dunes Resort Fully Remodeled Condo. Many upgrades and nuances to mention. Queens Grant is a lovely community of condos along the entrance way of Palmetto Dunes. A Premier full amenity Resort on Hilton Head Island. Offering Bike Rentals & Trails, Private Beach Access, 3 Top Golf Courses, Kayaking and Canoeing, Major Tennis and Pickleball Center, Restaurants, Corner Store along with central location to Island.

LocationOutdoor spacesWifi

Townhouse in Palmetto Dunes

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.

5.0 out of 5 average rating, 30 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!

LocationCheck-inAir conditioning

5.0 out of 5 average rating, 15 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

Outdoor spacesLocationComfort

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, 248 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!

ValueLocationBreakfast

Home in Hilton Head Island

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.

4.72 out of 5 average rating, 146 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!!

Outdoor spacesLocationLayout

Popular amenities for Hilton Head Island kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5.0 out of 5 average rating, 11 reviews

Home in Bluffton

Palmetto Nest

LocationValueGetting around

A spacious outdoor area is seen, featuring a large pool surrounded by loungers and lush greenery. The two-story house showcases a warm blend of muted exterior colors, with multiple outdoor seating options and a well-maintained garden accentuated by colorful flowers.

Home in Palmetto Dunes

Sunset Rentals | Lookout 2

Home in Hilton Head Island

4.91 out of 5 average rating, 11 reviews

Blue Heaven Oceanfront Condo in Hilton Head

LocationAmenitiesKitchen

5.0 out of 5 average rating, 13 reviews

Home in Daufuskie Island

Historic Home With Water Views

Outdoor spacesLocationView

Home in Hilton Head Island

4.72 out of 5 average rating, 146 reviews

Hilton Head Home

Outdoor spacesValueHeating

Other vacation rentals with a kayak

Townhouse in Palmetto Dunes

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.

4.94 out of 5 average rating, 35 reviews

Walk to Beach: Hilton Head Island Resort Gem

LocationOutdoor spacesAmenities

A dining table is set for guests on a patio overlooking the harbor. Colorful dishes and glasses are arranged alongside a bouquet of flowers. Boats are visible in the water, framed by palm trees and greenery in the background.

Villa in Shelter Cove

5.0 out of 5 average rating, 5 reviews

Condo on the Water at Shelter Cove Harbour!

LocationCheck-inBeach

A large swimming pool is surrounded by palm trees and lounge chairs. A gazebo with a green roof sits at the center of the pool. The ocean and a sunset sky are visible in the background, creating a serene setting.

Apartment in Hilton Head Island

5.0 out of 5 average rating, 3 reviews

LUXURY BEACHFRONT BARONY CLUB RESORT+AMENITIES

LocationFamilyCondition

Townhouse in Shipyard

New place to stay

Windward Village 123

2 Bd at Ocean Oak Resort, Hilton Grand Vacactions

Resort in Hilton Head Island

New place to stay

Marriott's Barony (Folly Field Beach) - HHI, SC

Superhost

A large pool area is surrounded by tropical landscaping, featuring a winding lazy river and a splash pad. Loungers with vibrant umbrellas are arranged around the pool, and the resort building rises in the background against a clear sky.

Charming two bedroom at Bluewater Resort

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.