Vacation rentals in Lake Kissimmee

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Top-rated vacation rentals in Lake Kissimmee

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

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Top guest favorite
Barn in St. Cloud
4.97 out of 5 average rating, 184 reviews

Rustic Barn Retreat

Experience the rustic elegance of this beautifully remodeled 1,800 sq. ft. barn nestled on a serene 17-acre property. Unwind in the private heated hot tub and soak up the peaceful surroundings. The prime location offers convenient access to major attractions—just a 35-45 min drive west will take you to Disney, Universal, SeaWorld, and gator parks, while a 45-60 min drive east leads you to the breathtaking Atlantic beaches and the Space Coast. Plus, the property is only 40 min from the airport

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, 107 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.

Top guest favorite
Cottage in Homeland
4.99 out of 5 average rating, 181 reviews

Garden Cottage at The Garden Gate Bed & Breakfast

At the Garden Gate, a fully licensed and professional bed and breakfast, we hope you will find respite; a quiet place to rest, relax and reconnect. The 1905 Garden Cottage, carefully restored and beautifully appointed, will be your home while you are here. Enjoy the view of the cottage garden and its seasonal vegetables and flowers from your front porch rocking chair. Fresh baked cookies and chocolates will greet you upon arrival and you will enjoy a full gourmet breakfast in the morning.

Guest favorite
Home in Lake Wales
4.94 out of 5 average rating, 127 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

Top guest favorite
A modern hot tub is set against a sleek black ceiling, with water that glistens under soft lighting. Surrounding seating includes gray chairs, and a flat-screen TV is mounted on the wall, enhancing the inviting space for relaxation.
Home in Winter Haven
4.98 out of 5 average rating, 123 reviews

Adult-Only Getaway w/ Mermaid Pool | 18+, Private

🗝️ Adults only. Ready to turn your vacation into an experience? Explore your fantasies at our romantic getaway, featuring four themed bedroom options* designed to inspire you. Bring your fave toys, experiment with our spicy 🌶️ amenities, or peruse our shop to bring home a little extra to keep the fire going after you leave. You will love our mermaid pool 🧜🏿‍♀️, jetted spa, & stone meditation deck while you soak up the sun or stargaze. 🌟 Your next adventure awaits. (*1 per 2 guests)

Top guest favorite
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, 135 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 favorite
A tranquil view of Lake Tulane is captured through a white picket fence. Sunlight filters through hanging Spanish moss on trees, casting reflections on the water's surface. A small boat with two individuals can be seen paddling in the calm lake, enhancing the serene lakeside atmosphere.
Home in Avon Park
4.92 out of 5 average rating, 116 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

Guest favorite
A rustic stilt house is positioned above a calm body of water, surrounded by lush greenery and water lilies. Large windows allow for natural light, reflecting the serene environment. The structure features a wooden exterior, harmonizing with the natural landscape.
Home in Lake Wales
4.91 out of 5 average rating, 101 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!

Guest favorite
Tiny home in Babson Park
4.92 out of 5 average rating, 409 reviews

Lil cedar tiny home, on crooked lake

Newly constructed tiny home.locatedon one of Florida's most prestigious lakes.crooked lake in s central floridais noted for its spring fed,clear water and white sand beaches,as well as it's amazing fishing and boating opportunities.the tiny house sits on 3/4 acre property overlooking crooked lake.the "million dollar view" as it's been called is spectacular at sunrise.the tiny house has an open ,airy, feel,with its comfortable roomy bedroom loft,and all the amenities of home.

Top guest favorite
A modern kitchen features gray cabinetry complemented by stainless steel appliances. A dining table with four chairs is positioned under pendant lighting. Natural light enters through two windows dressed with light curtains, casting a soft glow across the newly renovated space.
Home in Lake Wales
4.97 out of 5 average rating, 184 reviews

Linda Casita de Lake Wales

Cute older house with modern amenities. Located right downtown within a block from the playpark, Lake Wailes lake, walking path, and the historic downtown shopping area. All of the appliances in the home are brand new, as well as the washer and dryer. There is a large TV in the living room, as well as one in each bedroom - each with Roku and Netflix. Each bedroom also has a mini split A/C unit to sleep as cold, or hot, as you like. Parking is in the rear covered carport.

Top guest favorite
Treehouse in St. Cloud
4.97 out of 5 average rating, 1,129 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.

Top guest favorite
The tiny house and outdoor screened sitting area are illuminated at dusk, surrounded by trees. Warm light emanates from the windows, creating a cozy ambiance against the twilight sky. The natural landscape is peaceful, enhancing the connection with the outdoors.
Tiny home in Avon Park
5 out of 5 average rating, 102 reviews

Back to Nature!

Reconnect with nature at this unforgettable escape. There are acres of beautiful Hammock land to explore and enjoy. We are located on Arbuckle Creek, which is a wonderful canoeing experience (bring your canoe if you have the time)! We raise and sell USDA beef, so plan on purchasing a beef dinner if you desire! 😉🐄 Our tiny house is the perfect getaway to recharge your batteries! Come and enjoy all that Nature offers!

Popular amenities for Lake Kissimmee vacation rentals

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Lake Kissimmee