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
An aerial view captures the waterfront property surrounded by lush greenery and palm trees. The spacious lawn leads to a private dock, featuring a shaded gazebo and boat slips. The charming home is set back, complemented by a deck that blends with the serene lakeside environment.
Home in Lake Placid
4.98 out of 5 average rating, 56 reviews

Lakefront House, Chefs Kitchen, 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
Cottage in Lake Placid
5 out of 5 average rating, 65 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.

Superhost
Home in Lake Placid
4.71 out of 5 average rating, 7 reviews

Luxury Lakefront | Private Dock | Pool & Jacuzzi

Welcome to a luxury lakefront retreat overlooking the breathtaking waters of Lake Carrie. Spend sun-soaked days on your private dock & swimming beach, unwind in the pool & spa, or dive into adventure with the water trampoline, rope swing, kayaks, paddleboards & all beach essentials. Enjoy sunset dinners on the outdoor patio, grill in the full outdoor kitchen, gather around the firepit, & end the night with laughs in the game room. Designed for unforgettable moments shared with family & friends.

Top guest favorite
A serene courtyard is framed by lush greenery and palm trees, featuring a central fountain. Soft evening light illuminates the surrounding buildings, creating a calming atmosphere as the sunset reflects on the nearby lake.
Home in Lake Placid
5 out of 5 average rating, 13 reviews

Lake Front Oasisᨑ Prv Dockᨑ Poolᨑ Adults 18+ Only

Welcome to our stunning lakefront home nestled on the serene shores of Lake Grassy, Florida. This lovely retreat offers the ultimate escape for adults seeking tranquility and natural beauty near Lake Placid & Lake June. The perfect blend of comfort and Florida charm in this inviting 2 bedroom, 2 bathroom home featuring a cozy, screened lanai. This retreat promises a memorable escape for small groups seeking relaxation or lake adventure. 'LOVE' my listing to your Airbnb Wishlist to find later!

Guest favorite
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, 206 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
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, 145 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
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
4.97 out of 5 average rating, 39 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 favorite
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 favorite
A cozy seating area is featured, highlighted by a light-colored armchair with a patterned cushion. A floor lamp provides warm illumination next to a side table adorned with magazines and a decorative vase. Artwork with vibrant colors hangs on the wall above.
Home in Avon Park
4.92 out of 5 average rating, 109 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

Top guest favorite
A spacious dock area features several blue Adirondack chairs arranged facing the tranquil lake. The wooden structure is open, allowing for unobstructed views of the water and surrounding landscape. Natural light creates a calming atmosphere on the deck.
Cottage in Lake Placid
5 out of 5 average rating, 29 reviews

The Lazy Lakehouse Cottage on Lovely Lake June

Welcome to our happy place, The Lazy Lakehouse - private and cozy lakefront stay. Just Remodeled with modern conveniences. Sit on the dock and relax with a book and take in the sunset. The space includes a king bed, two queen beds and a queen sleeper sofa. Lake June in Winter is a sandy bottom, spring fed recreation lake. Bring your boat and tie up to enjoy Fishing, Waterskiing, wakeboarding, or enjoying the sandbar on the weekends with friends. No smokers.

Top guest favorite
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
4.96 out of 5 average rating, 28 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.

Top guest favorite
A charming, single-story home is situated on the edge of Lake Sebring, surrounded by a well-maintained lawn. A clear path leads from the entrance to the water's edge, where a private dock is visible in the background. The exterior features a light-colored facade with a welcoming orange door.
Home in Sebring
4.96 out of 5 average rating, 57 reviews

Lake Sebring Sweet Serenity-Waterfront

As soon as you walk in and look out the windows the serenity sinks in. This spacious and private 2 bedroom 2 bathroom new home with dock is located directly on Lake Sebring. Sweet Serenity is fully equipped with all your recreational needs. Fishing rods, gas grill, fire pit, canoe & kayaks are included with your stay. Bring your boat and drop it at the public ramp only 1/4 mile from the home. *NO PETS ALLOWED-NO EXCEPTIONS*

Popular amenities for Highlands County kayak rentals