Vacation rentals with a kayak in Highlands County

5 out of 5 average rating, 67 reviews

Cottage in Lake Placid

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.

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.

5 out of 5 average rating, 15 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!

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.

4.9 out of 5 average rating, 208 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!

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.

5 out of 5 average rating, 66 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 🍳 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 😀Host covers Airbnb fee

4.97 out of 5 average rating, 155 reviews

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

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!

4.98 out of 5 average rating, 44 reviews

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

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

4.92 out of 5 average rating, 109 reviews

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

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

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.

4.87 out of 5 average rating, 15 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.

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.

4.98 out of 5 average rating, 58 reviews

Lakefront Home w/ Private Dock + Water Trampoline

Discover our family-friendly lakefront retreat on beautiful Lake June in Winter. This 4-bedroom, 3-bath home is designed for effortless lake living, with a massive private dock, water trampoline, rope swing, paddleboards, canoe and grill. 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!

5 out of 5 average rating, 30 reviews

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

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.