Vacation rentals with a kayak in Highlands County

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Popular amenities for Highlands County kayak rentals

House rentals with a kayak

Guest favorite
A large oak tree stands beside the lake, its branches sprawling toward the sunset. On the shoreline, white lounge chairs are positioned on the grass, overlooking the calm water. The warm light reflects off the lake, enhancing the serene atmosphere.
Home in Avon Park
4.95 out of 5 average rating, 43 reviews

Sunset Beach Lake Front House

BradleyRating, 5 stars3 weeks ago
REPEAT GUEST. Beautiful home on the lake with gorgeous sunset evenings. A must stay 👍
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, 54 reviews

Stunning Lakefront Luxury Getaway

MelissaRating, 5 stars3 days ago
The home and location were absolutely beautiful. Tucked in the cove on Lake Henry, with a stunning dock view and patio area. The home was clean, and plenty of space for our big family to have room hanging out and in the kitchen. Would highly recommend the home and wonderful service and accommodations that Jennifer provided. Thank you for the great stay!
Top guest favorite
Home in Avon Park
5 out of 5 average rating, 50 reviews

Sandhill Retreat on Lake Letta

VinnyRating, 5 stars2 weeks ago
The home was beautiful, spacious, and has everything you need to enjoy you getaway. Huge dock has wonderful views and a great place to relax or fish. Janet was super accomodating and her communication is excellent, always responding quickly. The place is really clean and up-to-date, and the neighborhood is quiet and friendly. 100% reccommend if you need a place in the area as the pictures and descriptions Janet provides on the site are accurate. We enjoyed our stay and hope to book again next summer. Thank you Janet!
Guest favorite
A spacious single-story house is shown with a stone facade and a two-car garage. Soft lighting highlights the entrance, complemented by palm trees and a manicured lawn. The wet driveway reflects the nearby lights, creating a tranquil ambiance during twilight.
Home in Lake Placid
4.73 out of 5 average rating, 22 reviews

Pet friendly, access to Lake June

MelanieRating, 5 stars1 month ago
Darcee’s home was perfect for our family of 5. It had a ton of space for us to feel comfortable and like home. The house was in pristine shape.. had all the amenities and more that we needed. She was so flexible with our check in and addressed any questions prior to our arrival expeditiously. I would recommend her home immediately and do hope to go back and use it again!
Guest favorite
A welcoming living room is featured with a large window showcasing a view of the lake. A comfortable sofa is positioned next to a cozy armchair, and a light-colored coffee table is visible. A television is mounted on the wall, with a decorative door to one side.
Home in Avon Park
4.85 out of 5 average rating, 98 reviews

Private Lakehouse

JeffreyRating, 5 stars1 week ago
Chris was outstanding actually this is my second time using this location. We really enjoyed ourselves and Chris was always a call/text away from answering any questions that i had.
Top guest favorite
A spacious living area features a large sectional sofa adorned with a light throw blanket. A woven rug covers the floor, and a wall-mounted television is positioned above a cozy fireplace. Open shelving displays decorative items, while the kitchen is visible in the background.
Home in Lake Placid
5 out of 5 average rating, 39 reviews

Lake Placid Sebring LakeSide Story Lake House

MariliaRating, 5 stars3 days ago
Our stay was amazing! The hosts were amazing and VERY responsive. They were patient with my families endless questions, helped figure out a bunch of things and always communicated kindly. The place is great, there was 6 of us, everyone had a comfy bed. The kayaks , lawn games, Board games, chairs, ping pong table, grill, you think it they have it and we used it. Was awesome. Highly recommend.
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, 63 reviews

Private Old Florida Lake House Retreat

LauraRating, 5 stars1 week ago
We had a wonderful time and a great family reunion in this beautiful home. Every bedroom, bathroom and all common areas, including a terrific kitchen where immaculately clean and well appointed. The outdoor pool patio area was large and comfy with an outside kitchenette that took care of beverages and provided a grill for feeding our group. Our boat was easily tied up to a large dock, which also provided fun for the younger kids who enjoyed swinging into the lake. Watching the sunrise and set from the comfort of the screen patio was another treat. There was plenty of room for our family of 14 and God willing we’d love to return!
Top guest favorite
A serene lakeside view showcases a grassy area leading to Lake Sebring, with a white kayak resting on the shore. A boathouse and flagpole stand nearby, while a colorful cottage appears in the backdrop against a sunset sky filled with clouds.
Home in Sebring
4.97 out of 5 average rating, 127 reviews

Manatee Manor 3/2 House on Lake Sebring!

MariMarRating, 5 stars4 weeks ago
Absolutely perfect in every way! This was our second stay—and we’ve already booked our third because we just can’t get enough. The home is spotless, with exceptionally thorough cleaning and a clear sense of care and pride in every detail. Everything is beautifully maintained, from the fresh new carpet to the incredibly comfortable King bed in the master. The kitchen is fully stocked with everything you could possibly need, making it feel just like home. We also loved the thoughtful extras—bikes, kayaks, a peaceful netted seating area, and a private pier that made fishing on the lake a daily treat. The entire place has a warm, homey feel that makes it easy to relax the moment you arrive. The host is amazing, friendly, helpful, and genuinely invested in making your stay perfect. We couldn’t be happier and recommend this home 100% to anyone looking for a peaceful, well-equipped, and truly welcoming getaway. You'll love it here!

Cottage rentals with a kayak

Guest favorite
A serene outdoor seating area features four black Adirondack chairs arranged around a stone fire pit. Lush green grass surrounds the seating, and trees provide shade. In the background, Lake Sirena glistens under a clear blue sky, enhancing the peaceful lakeside atmosphere.
Cottage in Lake Placid
4.97 out of 5 average rating, 62 reviews

Lakefront Charming Cottage

BethanyRating, 5 stars1 month ago
I could go on and on about how amazing this place was!! 10/10 absolutely would recommend. Beautiful home with any amenity you could think of. So many wonderful touches here, truly so much care and thought put into it, that’s easy to see! Location was perfect as well. Beautiful property. We are already looking to book again for next year. If this place is available - book it!!
Top guest favorite
A modern lakefront home is framed by lush trees, draped with Spanish moss. The building features a wide, inviting porch with screening, surrounded by grassy areas. A long, straight walkway leads down to the dock, which extends towards the calm waters of the lake.
Cottage in Lake Placid
5 out of 5 average rating, 24 reviews

The Lazy Lakehouse Cottage on Lovely Lake June

AmandaRating, 5 stars1 month ago
This is our 3rd stay in the past year. We LOVE this place. Kelly is an excellent host and we feel at home at her lake house.
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, 60 reviews

Perfect secluded lake house retreat!

TamiRating, 5 stars3 weeks ago
Our stay here was wonderful! We will be back for sure! Michael was the best host. We had an issue and he took care of it immediately! Ryan came out in a timely manner and went above and beyond. They were pleasant, kind, and very helpful. Local recommendations were also great! The home is spotless and just a perfect peaceful place to enjoy some time away from your busy schedule. Thank you, Michael and Ryan you guys are the best!
Superhost
A wooden dock extends over the calm waters of Lake Henry, featuring two red Adirondack chairs positioned at the end. A swing hangs from a nearby tree, and a small boat is seen gently gliding across the lake in the background.
Cottage in Lake Placid
4.81 out of 5 average rating, 31 reviews

Tranquil 2/1 Cottage, deck & fire pit on Lake

KyleRating, 5 stars3 weeks ago
Charlie was very accommodating to us. We are remodeling our house and of course construction always takes longer than expected. Most serine view and felt like vacation essentially with the construction stress..
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, 26 reviews

Lake Retreat | Kayaks, Jacuzzi & Stunning Sunrises

MartinRating, 5 stars1 month ago
Beautiful grounds and impecable home. Fully stocked with everything you might need. Peaceful surroundings. Great place to disconnect. Guillermo was very responsive to any questions and welcoming. It’s a real hidden gem. Will be back for sure

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