Holiday houses in Lake Kissimmee

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Top-rated holiday rentals in Lake Kissimmee

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

A serene view of a dock extending into a calm lake at sunrise. The sun rises above the horizon, casting warm hues across the sky and reflecting on the water's surface. Reeds frame the scene, enhancing the natural surroundings.

Home in Lake Wales

4.89 out of 5 average rating, 37 reviews

Lakefront 2br w/pier & dock 4,500-ac Lake Rosalie

Peaceful getaway on Lake Rosalie w/ 4,530 ac of beautiful water w/ bass, catfish and crappie fishing. Birds routinely viewed from the dock include eagles, osprey, sandhill cranes, herons and more! Often making an appearance are a pair of otters and the Florida alligator! Morning sunrise over the lake from the sunroom or the dock is one of our favorite times! Add a cup of coffee is the best! Rowboat, golf cart, large patio w/grill and pier & dock to view the wildlife and enjoy time at the lake!

Superhost

A waterfront property is showcased, featuring a wooden exterior and a covered boat slip. Lush greenery surrounds the home, with a fire pit visible in the yard. The structure appears elevated, with a spacious deck above the boat area, providing picturesque canal views.

Guest suite in Haines City

4.84 out of 5 average rating, 109 reviews

2 BR 1 BA Lake House , Boat Slip, Pets, (king bed)

Escape to the perfect, peaceful pet friendly retreat with king bed. We are located on one of the 5 canals on Lake Hatchineha, the first of The Kissimmee Chain of Lakes. Connecting us to The Kissimmee River where you can rent a boat at Camp Mac and drive it home or bring your own boat and park it under cover in one of the boat slips.We are 45 minutes from Orlando airport or an hour from Tampa. 45 min to Disney's Magic kingdom/Universal Studios. 30 min to Legoland. Bok Towers free pass for 4.

Guest favourite

A bright and airy living space features a comfortable sofa and a coffee table atop a decorative rug. A ceiling fan and large glass doors lead to an outdoor area, while a sleek television adorns the wall opposite. Natural light enhances the neutral color palette.

Home in Lake Wales

5 out of 5 average rating, 34 reviews

Premium Lake Wales Getaway!

Beautiful townhouse, conveniently located in growing Lake Wales! Hotel-like feel with home-like comfort. Whether you're visiting for one night or planning an extended stay, this updated and stylish space lacks for nothing. We have you covered! Conveniently located near the infamous Bok Tower Gardens, Legoland, Peppa Pig Theme Park, with Disney World and world-famous, FL beaches within a couple hours away your options are endless. We hope you choose to stay with us for your special getaway!

Guest favourite

A two-story waterfront house features a welcoming entrance surrounded by lush greenery and palm trees. The exterior showcases a combination of gray siding and a balcony with white railing, offering a spacious front yard with a gravel pathway and decorative plants.

Home in Haines City

4.81 out of 5 average rating, 36 reviews

Jorgensen Lake House

No matter if you are looking to sit on the dock and fish, or enjoy a cocktail at our waterfront tiki bar, this place is for you. The third bedroom is handicap accessible on the bottom of the house with a separate entrance. Our waterfront house includes amenities such as wine fridge, above ground pool, dishwasher, wireless internet, washer and dryer. Located 45 minutes from Disney, 30 minutes away from Lego Land , and the Detroit Tigers Spring Training. Golf Courses as close as 10 minutes away!

Top Guest favourite

A wooden dock extends into the calm waters of Lake Rosalie, featuring a small viewing platform at the end. Lush green grass surrounds the water's edge, complemented by reeds along the shore. Clear blue skies reflect off the tranquil lake surface.

Home in Lake Wales

4.98 out of 5 average rating, 54 reviews

Lake Rosalie Getaway

Escape the hustle and bustle of life and enjoy a relaxing vacation at our newly remodeled lakefront home in beautiful Lake Wales! Located on peaceful Lake Rosalie, our residence is the perfect isolated getaway, yet still close to popular attractions such as Bok Tower Gardens, Legoland, Lake Kissimmee Park, Westgate River Ranch Rodeo and more! Unique amenities: - Large, upper-story wooden deck - 2 kayaks - Outdoor games, fishing poles - Exercise bike - Office room with printer - New kitchen

Guest favourite

Home in Lake Wales

4.92 out of 5 average rating, 131 reviews

Sunshine on the Lake | Boat Slip+Lakefront Fishing

Welcome to Florida Lakefront Paradise! ⭐️ Breathtaking Sunsets ⭐️ Bass Fishing ⭐️ Reserved Boat Slip ⭐️ Fish Cleaning Station ⭐️ Boat Wash Station ⭐️ Marina with Ice/Gas ⭐️ Large Fire Pit Area ⭐️ Located on Kissimmee Chain of Lakes ⭐️ Smart TV's ⭐️ Screened Lakefront Back Patio ⭐️ High Speed Internet ⭐️ Spacious ⭐️ Balcony Facing the Lake ⭐️ 30 minutes to Lego Land ⭐️ 20 minutes to Bok Tower Gardens ⭐️ 1 hour to Disney World ⭐️ 18 minutes to Spook Hill ⭐️ 18 minutes to Kissimmee State Park

Superhost

Home in Lake Wales

4.78 out of 5 average rating, 9 reviews

Wilderness Calls

Discover the charm of country living. Nestled among beautiful protected land and wildlife management area. Relax outdoors on the welcoming front porch or enjoy the views from the screened side porch, ideal for morning coffee, quiet evenings, or simply soaking in the surrounding nature. Inside, the home has a cozy layout with 2 bedrooms, downstairs with queen beds and 2 loft bedrooms upstairs with full-size beds. Boat ramps minutes away. 45 minutes from Legoland. 20 minutes from River Ranch.

Top Guest favourite

A cozy living area features two leather sofas positioned around a wooden coffee table with a glass top. In the background, a well-equipped kitchen with wooden cabinetry is visible. Natural light fills the space, enhancing the warm tones of the decor.

Cottage in Lake Wales

4.9 out of 5 average rating, 136 reviews

The "Little ‘Toa" Ideal for short & long stays!

Welcome to the Little TOA, Central Florida's fishing, hunting and winter get away. The house sits just off the Kissimmee River which is part of the Kissimmee chain of lakes, connecting Lake Hatchineha and Kissimmee. This will be a great spot for you and your buddies or family for a short weekend trip or an extended stay. Come see old Florida, the area holds many things to occupy your vacation time. *Your pet is welcome, please let me know ahead of time. There is a one time fee for pets.

Guest favourite

A large stilt house is portrayed above the serene waters of Kissimmee River, surrounded by lush greenery and lily pads. The structure features a wide porch and multiple windows, reflecting a rustic charm with the sky scattered with clouds in the background.

Home in Lake Wales

4.91 out of 5 average rating, 102 reviews

"Cutty Shack" Waterfront Kissimmee River House 3/3

"Cutty Shack" is the perfect fishing retreat. It is a 3 bedroom, 3 bath home built by our family in 1969. The Cutty Shack will sleep 6-7. This large stilt home (all living area is upstairs) is situated directly over Kissimmee River and right next door to Camp Mack River Resort. You and your group can enjoy peaceful evenings in the house, or walk next door to grab a drink and watch a "weigh-in". Our family has enjoyed this retreat for five generations and we hope you will too!

Top Guest favourite

A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.

Treehouse in St. Cloud

4.97 out of 5 average rating, 1,142 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Guest favourite

A spacious living area features a comfortable sofa complemented by decorative cushions. A large flat-screen TV is mounted on the wall, displaying a tropical beach scene. Natural light fills the space through sliding glass doors that lead to a patio, framed by light, airy curtains.

Home in Lakeshore

4.94 out of 5 average rating, 54 reviews

Secluded villa/pool/hot tub/ washer/dryer

Stress reliever. Own parking. 20 mins to Legoland, 20 mins from Warner College, 30 mins from Sebring, 45 mins south of Disney, 20 mins from Florida Skydiving Center. 8 mins from Westgate River Ranch. One Bedroom, bathroom, kitchen, patio, porch: Bedroom with king-size bed, 50 inch tv, large closet. Living room has comfy sofa with 70 inch Smart TV access. Resort-like community . fishing in the lake. Winter activities including karaoke, dances, bingo, concerts.

Superhost

Home in Lake Wales

4.67 out of 5 average rating, 3 reviews

Waterfront compound, sleeps 16, outdoor pavilion

Ready to reel in some fun?! This riverside hideaway near Camp Mack in Lake Wales sleeps 10 across 3 cozy buildings—perfect for families or fishing buddies! Cast a line from the dock, grill your catch under the pavilion, play some outdoor games, or unwind by the firepit under starry skies. With boat access to Lake Kissimmee and tons of outdoor charm, it’s the ultimate Old Florida escape. Come for the peace, stay for the fish tales