Vacation rentals in Kissimmee

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Kissimmee

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

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Top guest favorite

A classic two-story cottage with white siding and black shutters is set in a lush green yard. A wooden deck is adjacent to the house, offering views of the surrounding landscape and river. The property is bordered by a white picket fence and trees.

Home in Winfield

4.98 out of 5 average rating, 312 reviews

Riverbreeze Cottage• Waterfront• Great LLWS stay!

*30 min to LLWS *30 min to Knoebels *3 min to BU *Coffee, tea, snacks, some breakfast items provided *Pets welcome. No pet fee. Fenced yard *Discounts for multiple nights You'll enjoy river views/access and abundant amenities in this classic cottage-style home. Riverbreeze Cottage is an older home (built in the 1930s) that boasts wonderful character, unique decor and a cozy, charming feel. Reserve extra days now because you won't want to leave! Message the host with any questions and book today.

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Top guest favorite

A covered entryway is featured, leading to a gravel path. A small table and chairs are positioned under the overhang, accompanied by colorful planters. A rustic log planter displays vibrant flowers, while a well-lit exterior reflects the evening ambiance.

Home in Mifflinburg

4.96 out of 5 average rating, 156 reviews

The Logger's Den

Enjoy this newly renovated 2 BD, 1 Bath space located in White Springs perfect for a get away for two or for a family vacation. Nestled between two beautiful barn wedding venues making this a perfect stay for those far away guests. This property is only minutes from Penns Creek, perfect for fishing, kayaking, and picnicking. Some other near by areas include but are not limited to R.B Winter State Park, fly fishing in Weikert, hiking trails and various wineries. Only 45 minutes to State College.

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Guest favorite

A warm cabin interior features wooden walls and a cozy dining area with a long table and six chairs. A fireplace adds to the ambiance, while a chic chandelier hangs above. The kitchen, visible in the background, is equipped with modern appliances.

Cabin in Middleburg

4.91 out of 5 average rating, 145 reviews

Whispering Brook

Press your inner reset button by immersing your body and soul in nature’s calm. Enjoy tall pines, towering oaks, and a bubbling stream. Enjoy complimentary coffee on our screened-in porch, and take long, quiet walks in the pure mountain air. Grill or roast hotdogs and s’mores over the open fire. As darkness falls, appreciate the brightness of stars twinkling above a black forest night. Local Attractions: Shade Mountain Winery, T&D Cats, Middleburg Golf Course, Walker Lake (fishing and boating)

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Guest favorite

A rustic wooden swing is suspended between two trees, facing a calm stream. The swing features comfortable cushions. Surrounding the area, trees display autumn colors, enhancing the tranquil outdoor setting by the water.

Home in Mifflinburg

4.93 out of 5 average rating, 418 reviews

Creek Valley Cove

Enjoy an open concept newly furnished stream front rental on Penn’s Creek. This is a private country getaway to enjoy the outdoors or just relax. You can bring your kayaks and launch just steps from the house. Stay nice and warm by cozing up to the outside fire pit or enjoy the deck with a glass of wine by the fire table overlooking the water. Inside you can be pampered by the master bathroom’s whirlpool and enjoy the lavishing bedding that will make everything better. PLEASE NO FIREWORKS!

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Guest favorite

The modern A-Frame cabin features a sharp peak design with large glass windows that reflect natural light. A wrap-around deck is visible, surrounded by colorful autumn foliage, offering a serene outdoor space.

Tiny home in Sunbury

4.95 out of 5 average rating, 170 reviews

Sugar Shack| A-Frame Tiny Home w/ Hot Tub

Kick back and relax in this calm, stylish space. The Sugar Shack is a modern tiny home is located on top of a mountain and has spectacular mountain views. Sit on the wrap around porch with your loved one or relax in the hot tub right outside the door and enjoy watching the wildlife. The interior has a modern design and you will experience a cozy and romantic atmosphere the moment you walk in. It truly is a perfect spot to unwind and reconnect with yourself, your loved one, and nature!

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Superhost

A cabin with a wooden exterior is surrounded by greenery. The deck features black railings and steps leading up from the gravel path. A stone chimney rises from one side, complementing the rustic wooden structure.

Cabin in Millmont

4.85 out of 5 average rating, 125 reviews

"The Palomino" Cabin w/ Hot Tub on Penns Creek

Discover your perfect escape at The Palomino, a freshly renovated three-bedroom cabin nestled on the banks of Penns Creek. Known for its famed Green Drake hatch in late May, this area is a paradise for fly fishers. Enjoy a stylish white kitchen with rustic touches and a sleek black-tiled bathroom. Relax on the covered back porch with a grill and hot tub, or take in creek views from the front porch sitting areas. Ideal for fishermen, families, or couples seeking a serene getaway.

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Top guest favorite

The cabin's exterior features a welcoming front porch illuminated by warm lights, creating a cozy ambiance at dusk. Rocking chairs are arranged on the porch, offering a comfortable seating area. Stairs lead down from the porch to the gently sloped lawn, enhancing the outdoor space.

Cabin in Richfield

4.92 out of 5 average rating, 266 reviews

Hidden Pines Cabin in the Woods | Newly Renovated

This renovated cabin is perfect for a weekend getaway. Located on the beautiful Shade Mountain, it is a great spot to relax and unwind. Great for the family. Beds are two double beds, 1 single bed, a futon in our sitting room that sleeps 1 person. The cabin has running water, an indoor bathroom that includes a flush toilet, sink and a shower designed for shorten showers. A modernized kitchen has basic cooking accessories to prepare meals as well a coffee bar.

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Top guest favorite

The GeoDome is showcased from an exterior angle, highlighting its unique geodesic structure. Large clear panels reveal a cozy interior with a spacious bed and wooden flooring. The surrounding grassy area and evening sky suggest a serene outdoor setting.

Dome in Millerstown

4.94 out of 5 average rating, 239 reviews

GeoDome in the Country

This unique GeoDome is perfect for a cozy stay with your favorite person or as a relaxing getaway by yourself. Located in the peaceful countryside on the farm estate of The Homestead on Peanut Road. Few neighbors and an open sky create a perfect environment for star-gazing on clear evenings. Our dome is located on the edge of our family farm property across from the main Farm House. Enjoy an evening fire at the fire pit located just beside the GeoDome.

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Guest favorite

An outdoor seating area features a stone fire pit surrounded by Adirondack chairs. Soft string lights hang above, illuminating the space. The cabin, situated among trees, offers a view of the river, creating a serene atmosphere for evening gatherings.

Cabin in Millmont

4.93 out of 5 average rating, 231 reviews

Cabin On The River w/ Fire Pit, Kayaks + Bikes!

BNB Breeze Presents: Cabin on the River! This home is right on the banks of the renowned fishing stream, beautiful Penn's Creek. Escape the big-city crowds and enjoy the lovely ambiance from the private outdoors while being close to nearby towns, picturesque trails, state forests, restaurants, shops, and numerous attractions. - Outdoor Oasis w/ Deck, Picnic, Fire Pit + River Access! - Fully-Equipped Kitchen - Bikes & Kayaks - Smart TV - High-Speed Wi-Fi

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Top guest favorite

A bright and airy living space features large windows that fill the room with natural light. Comfortable seating includes a sleek black chair, a cozy armchair, and a leather couch. A decorative rug anchors the space, complemented by greenery near the windows.

Home in Liverpool

5.0 out of 5 average rating, 159 reviews

Hot tub, Pond, & Firepit on 8 acres!

Escape to this serene outback gem, ideal for couples, small families, or a group of friends looking for a peaceful retreat. ★ Enjoy breathtaking views of the night sky ★ Gather around the firepit near the pond for cozy evenings. ★ Explore 8 acres of natural beauty, complete with a stream and pond. ★ Meet our charming farm animals. ★ Ideal for personal reflection, family bonding, or quality time. This is the perfect spot to get away, reflect, and ponder.

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Top guest favorite

The cabin, featuring a distinctive green metal roof, is set against a backdrop of tall trees and snow-covered ground. A stone pathway leads to the front entrance, framed by windows and outdoor seating areas. Natural light is captured on a clear, sunny day.

Cabin in Millmont

4.94 out of 5 average rating, 137 reviews

Re imagined bank barn cabin.

Take it easy at this unique and tranquil getaway in mountains of Appalachia. The cabin is a remodeled bank barn, with the original beams and stonework, but with modern amenities. The outdoor spaces include a relaxing front porch, a stamped concrete patio, and fire pit with smokeless solo stove, and easy access to bald eagle state forest, and Penns creek.

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Top guest favorite

A charming cottage is nestled among trees, featuring a stone exterior and large windows that provide a view of the surrounding woods. A gravel path leads to the entrance, while a spacious yard is seen in front, enhancing the serene setting.

Cottage in Mifflinburg

4.98 out of 5 average rating, 252 reviews

Cozy Pines *Sweetheart* Cottage

Enjoy a romantic vacation at this beautiful little cottage tucked away in the woods. No TV means you can enjoy the surrounding nature and your loved one. Deer, raccoons, and foxes share the spacious front yard. Take a walk along a tributary of Buffalo Creek as it meanders through the woods, or relax and take it easy at this unique and tranquil getaway.

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