Vacation rentals with a kayak in Highlands County

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Top-rated kayak rentals in Highlands County

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Top guest favorite

A private dock extends into the serene water, featuring a covered seating area and a jumping platform. Several inflatable paddleboards are secured nearby, with lush greenery and palm trees lining the shore, providing a tropical backdrop to the tranquil scene.

Home in Lake Placid

4.98 out of 5 average rating, 46 reviews

Lake June Getaway – Game room, Water Trampoline

Discover our family-friendly retreat in beautiful Lake Placid, Florida! This 4-bedroom, 3-bath home is geared to enjoy the lake to its fullest. From a massive private dock, jumping platform & ropeswing, to paddleboards & canoes, we have the lake life covered. Just show up and enjoy! Inside offers a stunning kitchen, newly renovated bathrooms, spacious living and a game room that features ping pong, shuffleboard and board games. Your ideal getaway, blending relaxation and excitement starts here!

Top guest favorite

A single-story home is set against a backdrop of trees, featuring a spacious yard with green grass. The building has screened-in porches and a large parking area visible for RVs and trailers. Nearby, a stone fire pit and several seating areas are located by the water.

Cottage in Lake Placid

5 out of 5 average rating, 63 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.

Top guest favorite

A large boat dock extends into the expansive lake, with space to accommodate multiple boats. The tranquil water reflects the sky, dotted with fluffy white clouds. A grassy shoreline is visible, enhancing access to the lake.

Home in Lake Placid

4.98 out of 5 average rating, 64 reviews

Private Old Florida Lake House Retreat

This extraordinary "Old Florida" luxury living lake house offers large open living spaces with calming views. Grill out on the screened-in back patio, watching the sunset on the private beach while the kids jump off the dock. On chilly nights, get the fire pit going or take a long soak in the hot tub. Whether you’re here to relax, entertain, or get out on the water, we’ve got you covered. Bring your furry friend, he's a part of the family too! (Pet fee required, please discuss before booking).

Guest favorite

Home in Lake Placid

4.9 out of 5 average rating, 199 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 favorite

A cozy fire pit area is surrounded by colorful Adirondack chairs, with a view of the lake and sunset in the background. A wooden dock extends into the water, framed by palm trees and a partially cloudy sky, creating a peaceful outdoor setting.

Home in Lake Placid

5 out of 5 average rating, 24 reviews

Newly Renovated Lake June home with private beach

Book soon and come enjoy the sun, lake fun and private beach! Thrive4life is our family's happy place and we want you to make it yours! Kick off your shoes and dig your toes in our private beach. The water views are the star of the show. Located at the beautiful Lake June, this beautifully landscaped retreat serves up the best Lake June has to offer. The beach with a fire pit is a perfect place to soak up the sun during the day or enjoy an evening drink or smore's by the fire as the sun sets.

Superhost

A screened-in porch features a small wooden table set with a snack and a vase of flowers. Two folding chairs are positioned around the table. A cushioned bench and colorful pillows line one side. The view includes palm trees and the calm waters of Lake Tulane.

Home in Avon Park

4.91 out of 5 average rating, 105 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. Instagram @laketulanecottage The space Relax, kick back in the peacefulness of our little paradise which sleeps up to 6 guests with all of the comforts of home, including high speed internet. 20 minutes from Sebring Raceway, 15 minutes from Highlands Hammock State Park, 30 min from Lake Placid

Guest favorite

A panoramic view highlights a serene lakeside property surrounded by lush greenery. A dock with a water slide extends towards the glassy lake, while a fire pit area is framed by seating. The landscape features a combination of forest and open lawn that enhances the tranquil atmosphere.

Cottage in Sebring

4.96 out of 5 average rating, 28 reviews

Lake Retreat | Kayaks, Jacuzzi & Stunning Sunrises

Welcome to your lakeside retreat — 6+ acres of peaceful, private nature where time slows down and serenity takes over! Wake up to unforgettable sunrises, paddle across glassy waters, and unwind as the sky turns gold at sunset. Surrounded by quiet forest and lake views, this home is designed for reconnection — with nature, with loved ones, and with yourself. Whether you're reading by the dock, soaking in the jacuzzi, or simply breathing in the silence, this is your escape from the everyday!

Top guest favorite

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

4.97 out of 5 average rating, 116 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 favorite

A screened porch offers comfortable wicker seating with light cushions and a round table at the center. Decorative pillows with the word 'LAKE' are displayed on the sofa. The expansive view reveals a grassy yard leading to the lake, with colorful chairs arranged nearby.

Home in Lake Placid

4.99 out of 5 average rating, 89 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 !

Guest favorite

Bright yellow flowers are positioned in the foreground, while tranquil water reflects the clear blue sky. A wooden dock extends into the lake, partially shaded by overhanging moss-covered trees, creating a serene atmosphere ideal for relaxation.

Bungalow in Lake Placid

4.87 out of 5 average rating, 62 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.

Top guest favorite

The open dining area features a large wooden table surrounded by eight brown chairs. Natural light fills the space, highlighting modern kitchen appliances and cabinetry in the background. Sliding glass doors offer views of the outdoors, blending the interior and exterior seamlessly.

Home in Lake Placid

5 out of 5 average rating, 56 reviews

Stunning Lakefront Luxury Getaway

🌅 Lakefront on Lake Henry 🚣‍♀️ Kayak to Lake June-Kayaks provided! 🎉 Outdoor Paradise: Dock for fishing, kayaks, boat lift, two grills, +more! 🍳 Gourmet Kitchen: Fully stocked with all the supplies and tools any chef would want! 🛌 Super Comfortable Beds and Interior Decor 🏖 Fun Guaranteed: Board games, foosball, pool table, life-sized wall scrabble, puzzles, books, and more! 🐕 Pets Welcome 🌐 Fast Internet 🏎️20 minutes to Sebring Track 😊 24/7 Local Host Support

Top guest favorite

The exterior of the lake house features a well-maintained lawn with lush green grass and colorful flower beds. A light-colored façade contrasts with the vibrant blue sky and a large tree provides shade nearby. The entrance is marked by a stylish door and decorative elements.

Home in Lake Placid

5 out of 5 average rating, 15 reviews

Henry's Lake House Waterfront Oasis

Escape to tranquility at our serene lake house, where peace and relaxation await. Nestled by the water, this idyllic retreat offers a perfect blend of seclusion and convenience. Enjoy the calming views of the lake while being just a short drive away from all the essentials. Whether you're looking to unwind with nature or explore nearby attractions, our lake house provides the ideal getaway.