
Holiday rentals with a kayak in Hilton Head Island
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Hilton Head Island
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Ocean Dunes 111 Oceanfront view Heated Pool 1stflr
Welcome to **Ocean Dunes 111**! This renovated 1-bedroom, 1-bath condo features a **queen bed**, **leather sofa bed**, and **updated bunk beds** for 6 guests. The kitchen has **stainless steel appliances**, a **Keurig** (bring K-cups), and essentials. Enjoy **smart TVs**, **Spectrum cable**, and **Wi-Fi**. Relax on the **private balcony** with a **partial ocean view** and use the provided **beach chairs**. Perfect for families or small groups. Just steps from the beach, shops, and restaurants.

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.

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.

2 pm Checkout - King Bed - Indoor Pool - Beach
** Free 2 pm checkout offered from November 2025 - February 2026 ** 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.

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.

ThisISOceanfront! ESA! PetsAllowed! 2BR/2BA condo
Enjoy breakfast, peace and luxury at this large oceanfront 2BR/2BA condo. ESA Pets allowed! 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!

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!

Marriott's Harbour Point - 2BR/2BA - Waterfront!
Next to picturesque Shelter Cove Harbour on Hilton Head Island, you will find Marriott's Harbour Point and Marriott's Sunset Pointe Resort, quite possibly one of the most underrated locations on HHI. Enjoy outstanding direct waterfront views of Broad Creek from your private balcony in the morning and amazing sunsets in the evening. Watch the boats entering and leaving Shelter Cove marina along with the opportunity to see local wildlife including dolphins and many varieties of birds.

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!

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

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!

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.
Popular amenities for kayak rentals in Hilton Head Island
House rentals with a kayak

Waterfront Paradise in the heart of the Lowcountry

Spacious 4BR Waterview Dog Friendly

Hilton Head Home

Luxe 4BR Waterview | Private Pool | Dock | Deck

Ocean-View Treetop Escape w/ Fire Pit!
Other holiday rentals with a kayak

Ocean Dunes 111 Oceanfront view Heated Pool 1stflr

Marriott Harbour Club - 2BD

Queens Grant Gem - Luxury Remodel - 2/2 - King Bed

Riverfront Cedar Bluff Cottage Old Town Bluffton

2 pm Checkout - King Bed - Indoor Pool - Beach

Hilton Head Home

Coastal 2Bdrm Stay | Pool Access, Walk to Beach

ThisISOceanfront! ESA! PetsAllowed! 2BR/2BA condo
When is the best time to visit Hilton Head Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $478 SGD | $491 SGD | $491 SGD | $491 SGD | $491 SGD | $452 SGD | $397 SGD | $391 SGD | $372 SGD | $483 SGD | $478 SGD | $491 SGD |
| Avg. temp | 10°C | 12°C | 16°C | 19°C | 23°C | 27°C | 28°C | 28°C | 25°C | 20°C | 15°C | 12°C |
Quick stats about holiday rentals with a kayak in Hilton Head Island

Total holiday rentals
Explore 50 holiday rentals in Hilton Head Island

Nightly prices starting at
Hilton Head Island holiday rentals start at $142 SGD per night before taxes and fees

Verified guest reviews
Over 950 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
50 of Hilton Head Island holiday rentals include wifi 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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- Rentals with a kayak Beaufort County
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- Coligny Beach Park
- Forsyth Park
- Hunting Island State Park Beach
- North Beach, Tybee Island
- Harbour Town Golf Links
- The Westin Savannah Harbor Golf Resort & Spa
- Shipyard Beach Access
- Tybee Beach Pier and Pavilion
- Bradley Beach
- Mid Beach
- Harbor Island Beach
- Secession Golf Club
- Tybee Beach point
- Dolphin Head Golf Club
- Bull Point Beach
- Wormsloe Historic Site
- Congaree Golf Club
- Driftwood Beach
- Bonaventure Cemetery
- Long Cove Club
- Seabrook Island Beach
- Hunting Island Beach
- The Beach Club
- Edingsville Beach
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