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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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 Shelter Cove

4.83 out of 5 average rating, 76 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

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

4.89 out of 5 average rating, 82 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.

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

4.78 out of 5 average rating, 41 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 serene outdoor space featuring a private pool surrounded by lush greenery. The inviting pool is complemented by a spacious deck, and the home in the background has large windows and access to the outdoor area. Sunlight filters through the trees, creating a peaceful ambiance.

Home in Palmetto Dunes

5 out of 5 average rating, 6 reviews

26 Port Tack | Dog Friendly | Pool | Lagoon View

PROPERTY AMENITIES Free Wi-fi Smart TV’s | DVD Keyless Entry Keurig Washer & Dryer (in-unit) Pool and Spa Game Room PROPERTY CONFIGURATION 4 Bedrooms 2 Bathrooms Sleeps 10 1 King | 3 Queen | 1 Twin | 1 Sleeper Sofa Max Parking of 6 Vehicles BEACH ACCESS Parking for the beach is located at the Dunes House or a walk/bike ride to the beach is a half mile from Port Tack to Mooring Buoy. PROPERTY REMINDERS 4-night min stay required Pool/spa heated (add'l fee) Dog Friendly (add'l fee)

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

4.95 out of 5 average rating, 129 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 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, 229 reviews

Coastal 2Bdrm 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

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

4.86 out of 5 average rating, 44 reviews

30% off July4thWeek Oceanfront2BR/2BALuxuryCondo

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!

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 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

Two kayaks are positioned on the grassy edge of a serene lagoon, featuring vibrant orange and blue colors. A wooden dock extends into the water, framed by lush trees and a clear sky, inviting exploration and relaxation in the tranquil surroundings.

Townhouse in Palmetto Dunes

5 out of 5 average rating, 4 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

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, 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 Sea Pines

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.

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

5 out of 5 average rating, 31 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.

Vacation rentals for every style

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Villas

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Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Hilton Head Island kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

Top guest favorite

A spacious living area is featured, with comfortable seating provided by soft armchairs and a large sofa. A ceiling fan circulates air above. Natural light floods the area through large windows, while a fireplace and a TV add to the room's functionality.

Home in Saint Helena Island

5 out of 5 average rating, 11 reviews

One Particular Harbor

SallyRating, 5 stars6 months ago

We loved staying at Lauren’s place! She decorated it beautifully and even put out the Christmas decorations for our family Thanksgiving weekend. The house was so festive. The beds were extremely comfortable. We enjoyed watching the alligators and the turtles behind the house in the waterway from the balconies! The beach was gorgeous on a cold winter day and we went for long walks and several golf cart rides. We felt completely at home and Lauren was so sweet and such an incredible communicator. Thank you for everything!!!!

Superhost

An outdoor seating area features four wooden chairs arranged around a circular fire pit, set on a pebble path. Soft lights are strung overhead, illuminating the space against a backdrop of lush greenery and a tranquil lake at sunset.

Home in Savannah

4.9 out of 5 average rating, 31 reviews

Lakefront Carriage House near Savannah & Tybee

SteveRating, 5 stars2 months ago

The Lakefront Carriage House is beautifully situated on a private lake in a residential neighborhood right between Savannah and Tybee, making it the perfect home-away-from-home for enjoying the area. We appreciated the bright, modernist decor, and the host was very friendly and responsive. I wish the gas tank for the fire pit was full, and I would definitely recommend bringing bug spray, but overall we loved our stay and can't wait to return!

Guest favorite

The bungalow-style cottage features a light grey exterior complemented by a front porch. A warm entryway is framed by shrubs and trees, with a large window on one side allowing natural light to enter. A clearly defined pathway leads to the entrance.

Home in Beaufort

4.93 out of 5 average rating, 59 reviews

Peaceful Cottage on the Marsh, Close to Downtown

AnneliseRating, 5 stars2 weeks ago

Wonderful stay while in town for a wedding. Enjoyed all the extras the home comes with: kayaking with the kids during high tide and the pass to the beaches at Huntington State Park. Also, the kitchen was stocked with all the cooking tools we needed plus a cabinet of spices which was appreciated. Great access to downtown and walkable to Starbucks for morning coffee.

Top guest favorite

A heated swimming pool features clear water surrounded by a stone deck, with lounge chairs positioned for relaxation. An outdoor kitchen and dining area are visible, enclosed by a wooden fence for privacy, while lush green grass adds a natural touch to the ambiance.

Home in Savannah

4.9 out of 5 average rating, 167 reviews

Blue Kayak House - Heated Private Pool

MichaelRating, 5 stars8 months ago

We had a great stay. This is a well established community with quick and easy access to all of the areas attractions. Very quiet. Never heard any noises or neighbors. Plenty of space and the backyard and pool are so well designed and installed. Heated pool came in handy as we had some cool weather a few days. Kitchen appliances and laundry equipment are new. We thoroughly enjoyed our visit.

Guest favorite

A tranquil sunset casts vibrant colors over the water, reflecting on the creek. A wooden dock extends over the water, leading to a cozy seating area with a table and chairs, surrounded by tall grass and serene nature.

Home in Tybee Island

4.95 out of 5 average rating, 81 reviews

Creekside Oasis- pool, waterfront hot tub, dock

AdeleRating, 5 stars1 week ago

What a wonderful place at Tybee Island for Our family to enjoy! We fished, enjoyed the beach nearby, made a bonfire, cooked, dined out at some of the wonderful restaurants including the only Brewery on the Island that had spectacular food😉, enjoyed a quick ride into Savannah for a special day, and relaxed in Emily’s great place! Was truly very special and wonderful to be able to get precious time together with our family!

Top guest favorite

An outdoor seating area features four Adirondack chairs arranged around a fire pit, situated on a brick patio. Lush trees surround the space, with a tranquil lake visible in the background. A dock extends into the water, enhancing the serene environment.

Home in Savannah

5 out of 5 average rating, 41 reviews

Low Country Lake Retreat

DanielRating, 5 stars2 weeks ago

Came to Savannah for a birthday weekend with friends and family and couldn’t have been any better. Had a great stay at Jill’s home and would highly recommend to anyone considering staying in Savannah. Can’t beat its amazing scenery and how close it was to the downtown/beach.

Guest favorite

A custom beachfront home with light purple siding features a spacious balcony and off-street parking beneath. The lush green lawn is bordered by palm trees, and expansive blue skies create a serene backdrop, enhancing the home's inviting curb appeal.

Home in Saint Helena Island

4.99 out of 5 average rating, 127 reviews

The Hampton House

Susie BaerRating, 5 stars1 month ago

Thoroughly enjoyed our stay at The Hampton House! The house was comfortable and clean and had everything we needed. Location on the water can not be beat. All the beach toys and kayaks were a bonus. Derrick was super responsive and helpful. We would definitely come back. Highly recommend.

Superhost

A modern kitchen is presented, featuring gray cabinetry and stainless-steel appliances. A wooden dining table with two striped chairs occupies the space. A large refrigerator and a gas stove are visible, along with a white tiled backsplash that enhances the overall design.

Home in Midtown

4.86 out of 5 average rating, 153 reviews

Cute Studio in Starland

MarshallRating, 5 stars4 days ago

Cozy little frog! Quick ride share to downtown. We appreciated the privacy fence while we enjoyed the fire pit! And when the rain changed our day plan, it was a very cozy day inside. Alex’s communication is exactly what you’d want in a host!

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Cottage rentals with a kayak

Top guest favorite

Cottage in Tybee Island

4.99 out of 5 average rating, 137 reviews

Couples Retreat FREE Golf Cart/Bikes/Kayaks + Dock

KellyRating, 5 stars2 days ago

We had a wonderful stay at the cottage. The swing bed on the porch is fabulous! I could have stayed there the whole time. It is such an easy trip to the beach with the golf cart.

Top guest favorite

A charming cottage is set amidst lush greenery, featuring a wide, welcoming pathway made of patterned pavers leading to a spacious deck. Large windows reflect natural light, and a few outdoor chairs are positioned under umbrellas, inviting relaxation in the shaded area.

Cottage in Beaufort

4.98 out of 5 average rating, 178 reviews

Private Island Cottage

AlisaRating, 5 stars1 week ago

This was a girls trip with my 3 daughters. We wanted to stay on one of the rivers. My daughters are 27, 25 and 20. They absolutely loved it. We were ticked back in the lines and palm trees. It felt very private but we were at the very end of a very nice and private community. They had everything available for a great vacation…. Hot tub, fire pit, paddle boards, kayaks, life vests, golf carts, etc. we hated to leave. Joni responded within seconds to any message we sent her. They were great hosts.

Top guest favorite

A cozy cottage stands illuminated at night, featuring a welcoming entrance. A fire pit with glowing flames creates a warm ambiance in the foreground, surrounded by natural landscaping. The surrounding trees add to the serene atmosphere, enhancing the sense of privacy.

Cottage in Beaufort

5 out of 5 average rating, 132 reviews

Private cottage in the pines

JillRating, 5 stars3 days ago

The cottage was clean and comfortable and close to many wonderful places to see in the area. The bed was very comfortable...a big plus! Chris was very helpful and accomodating with our questions and needs. He was quick to respond and went above and beyond to make our stay as good as it could be.

Top guest favorite

A colorful hammock is nestled among lush greenery, featuring vibrant patterns. A person reclines comfortably on the hammock, enjoying a refreshing drink. Sunlight filters through the leaves, creating a serene outdoor atmosphere that invites relaxation.

Cottage in Tybee Island

5 out of 5 average rating, 55 reviews

TIKI Couples Retreat, FREE Golf Cart/Bikes/Hot Tub

LauraRating, 5 stars5 days ago

Fantastic! We loved the decor and all the amenities, especially the golf cart and the hot tub! Great location and cute cottage, I would highly recommend this place and Missy!

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