Holiday rentals with a kayak in Highlands County

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Top-rated rentals with kayak in Highlands County

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

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Top guest favourite
Cottage in Lake Placid
4.99 out of 5 average rating, 69 reviews

Perfect secluded lake house retreat!

Retreat to the perfect combination of peace and quiet. Spacious 2 bedroom home on a private lake stocked with bass and other fish to spend the day with your friends and family. If you are into ATV and off-roading, there are 100's of miles of trails to ride straight out the front driveway. The home currently has two queen beds and a queen air mattress. We also have access to Lake June and the private Sun N Lakes boat ramp and park. Boat ramp is by key.Plenty of parking for your trailers and rvs.

Guest favourite
A serene view of a lake at sunset is captured, with vibrant hues of orange and pink reflecting on the water's surface. Tall grasses frame the image, while a wooden dock is visible in the distance against the backdrop of a colorful sky.
Home in Lake Placid
4.9 out of 5 average rating, 209 reviews

Lake Huntley Oasis - Pvt Dock - 1/2 Acre - Kayak

Live the lake life! Watch the sun set over Lake Huntley from your kitchen window and firepit; explore the lake by docking your watercraft (or rent ours) in your backyard, or use our included tandem kayak, canoe, SUP. This cozy house has 3 bedrooms, 2 bathrooms and sleeps up to 9 comfortably. Enjoy plenty of living space, a large screened-in porch, full kitchen, fire pit and BBQ grills. The house also includes onsite laundry, EV charger, RV hookup & parking. Kitchen completely renovated in 2024!

Top guest favourite
An aerial view captures the lakefront property, showcasing a sandy beach, a private boat house, and a wooden dock extending into the lake. Lush greenery surrounds the home, and kayaks are visible along the shoreline, highlighting the outdoor recreational opportunities available.
Home in Sebring
4.98 out of 5 average rating, 160 reviews

LakeFront Sunrise Cottage

Catch sunrises or fish at this 2/1 lakefront house with sandy beach and private boat house! This cheery cottage is perfect for sunrises with coffee or exploring beautiful Lake Sebring on kayaks (included with booking). Plenty of parking onsite (bring your boat trailer), you will love this oasis on the lake! We want your stay to be pleasant and carefree so we do not require our guests to do any dishes, laundry, or other cleaning when checking out. Our housekeeping crew will take care of you!

Top guest favourite
Aerial view of a serene lake surrounded by lush greenery and expansive open spaces. A dock extends into the water, and trees create a natural border. The vibrant sky reflects golden hues as the sun sets, enhancing the peaceful atmosphere of the property.
Villa in Sebring
4.98 out of 5 average rating, 52 reviews

Lake Retreat | Wellness & Spa | Kayaks | Sunrises

Trade noise and traffic for glass-smooth lakefront living! Wake up to open skies and a private lake surrounded by 6+ acres of nature. Made for slow mornings, barefoot walks, sunrise paddles from your private dock and star-filled nights in the hot tub. Spend the day journaling by the water, in the outdoor gym, kayaking, then unwind in the jacuzzi or by the fire. Time slows and the lake becomes your daily ritual. Lakefront Retreat • Jacuzzi • 6+ Acres • Private Dock • Family • Sports Games

Top guest favourite
A serene lakefront view features a sandy beach with four colorful Adirondack chairs arranged on the grass. A wooden dock extends into the lake, leading to two covered seating areas. Gentle waves ripple under a clear blue sky, complemented by peaceful clouds.
Home in Lake Placid
4.99 out of 5 average rating, 92 reviews

Lakefront Recreation & Relaxation in Lake Placid

Lakefront home completely remodeled with functionality, comfort and design in mind. Located on beautiful sandy bottom Lake Francis with private beach and large yard. Everything you need for a lake getaway including tubes, floats, chairs, umbrella, jon boat & 2 Kayaks, fishing rods, volleyball and skis. Bring your watercraft and tie up to the private dock. Or, kick off your shoes, relax in the screened in porch and take in lake views, breezes and backyard wildlife . . . the friendly kind !

Top guest favourite
Bungalow in Lake Placid
4.88 out of 5 average rating, 68 reviews

Bella’s Bungalows on Lake June seasonal discounts

Relax, You are steps away from Lake June in Winter, an anglers and boating paradise. Soft white sandy bottom makes Lake June the premier lake in Highlands county. While Highlands county is known for its wide variety of lakes, only sandy bottom lakes are perfect for all water sports including swimming. The cottage is family friendly and filled with fun, whimsical decor. Just hours from most major cities in Florida, it’s like stepping back in time to a more relaxed and simpler way of life.

Guest favourite
An aerial view showcases a spacious home with a brick-paved driveway and a well-maintained lawn. The property is bordered by a white fence, with a dock and a boathouse visible on the serene water's edge in the background.
Home in Avon Park
4.88 out of 5 average rating, 129 reviews

Lake Denton Diver's Paradise Swim-Dive-Boating

Experience Lake Denton, a crystal clear 50’ deep spring fed diver’s lake where the water is so clear you can watch fish swim beneath you. There is a reason people like Tiger Woods, Whistlin Diesel, Mel Tillis and others have swam here. This family friendly getaway offers a private waterfront setting with unforgettable sunsets from the boathouse. Enjoy swimming, fishing, grilling, water toys and in water volleyball. Kayaks provided, Public boat ramp access. Voted Nicest Lake in Florida

Guest favourite
A serene lakeside view is presented, showcasing a vibrant sunset with hues of orange and purple reflected on the water. Palm trees and Spanish moss frame the scene, creating a tranquil atmosphere. A pathway leads through lush greenery toward the lake.
Home in Avon Park
4.92 out of 5 average rating, 111 reviews

Charming Lake View 1935 Cottage

Go back in time in this beautiful 1935 Florida Cottage, overlooking Lake Tulane in the charming little town of Avon Park. Two living areas, one with a fireplace and one with a view of the lake. @laketulanecottage 🛏️ Bedroom Queen bed 🛏️ Bedroom Full Bed 🛏️ Pull out couch ✅ Coffee maker, toaster, blender & cookware ✅ Dishes, silverware & baking essentials ✅ Dining area (seats 6) ✅ Central A/C & heating ✅ High-speed Wi-Fi ✅ Washer & dryer in unit ✅ Driveway parking

Guest favourite
An inviting lakeside property is surrounded by lush green grass and shaded by tall trees. A paved driveway leads to a bright blue door, while the tranquil lake is visible in the background, enhancing the natural beauty of the setting.
Home in Lake Placid
4.88 out of 5 average rating, 17 reviews

Muz Lake House

Discover a breathtaking lakeside retreat on the serene shores of Lake Sirena, known for its peaceful atmosphere. This exquisite home, set on a generous half-acre lot, boasts 120 feet of sandy beach frontage. It offers ample space for both relaxation and outdoor activities. Enjoy quality time with family or friends, fishing, or kayaking, all against the stunning backdrop of spectacular lake sunsets. This property provides the perfect escape for creating unforgettable memories.

Top guest favourite
The inviting entrance features a vibrant orange door framed by a light blue accent, set within a cottage-style facade. A wooden staircase leads up to the porch, where potted plants add a touch of greenery to the welcoming area.
Guest suite in Lake Placid
4.98 out of 5 average rating, 50 reviews

Lake Placid Cottage with Lake Access & EV Charger

Quiet and quaint cottage just minutes from downtown Lake Placid. Enjoy peaceful moments on the porch our lake access dock just across the street. Explore the murals, shopping and dining in our historic district. We have the perfect home away from home when coming for the Sebring races, Caladium festival, arts and crafts festival, or just some rest and relaxation. Cottage has one bedroom with a queen-sized bed and a sofa that fully reclines for an additional guest.

Guest favourite
A cozy bedroom features a four-poster bed draped in soft fabric. Complementary pillows and a textured blanket adorn the bed. A large mirror and a wall clock are visible in the background, enhancing the room's space. Warm lighting contributes to a welcoming atmosphere.
Cottage in Lake Placid
4.97 out of 5 average rating, 67 reviews

Lakefront Charming Cottage

Kick back and relax in this calm, stylish lakefront property. Whether traveling for business or pleasure, this beautifully decorated cozy cottage will make you feel right at home. Less than a mile from downtown Lake Placid, take a short ride or a casual walk to a local restaurant, coffee shop or the local brewery. Enjoy Lake Sirena in our back yard or make a day trip to the beaches on the east or west coast, only about 1.5 hours in each direction.

Top guest favourite
A serene lake view is presented at sunset, with warm hues reflecting off the water. Silhouetted trees frame the scene, while a dock extends into the lake, providing a pathway for various activities. Gentle ripples suggest a calm atmosphere in the quiet surroundings.
Home in Avon Park
5 out of 5 average rating, 61 reviews

Sandhill Retreat on Lake Letta

Bring your kids and pets to this spacious lake house in a quiet neighborhood. Boat, fish, jet ski, kayak, or just relax by the lake. Observe the varied wildlife, including sandhill cranes, herons, otters and ducks and enjoy beautiful sunsets, while sitting in the yard under grand oak trees or on our newly refurbished dock. We are centrally located with easy access to Orlando and Tampa.

Popular amenities for kayak rentals in Highlands County