Holiday rentals in Kissimmee

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Top-rated holiday rentals in Kissimmee

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

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Guest favourite
A well-equipped kitchen featuring light cabinetry and a spacious island at the center. Stainless steel appliances include an oven and microwave. Natural light filters through windows, illuminating the room. Decor accents include a flower arrangement and textured rug, providing a functional yet inviting space.
Farm stay in McAlisterville
4.9 out of 5 average rating, 143 reviews

Peaceful Mountain View Farmhouse w/ Whirlpool Tub

Relax with the family at this peaceful place in the country. Sit on the spacious deck to enjoy the view of the mountains and farmland. Spend time biking in the rural area that seems to go back in time. Watch the cows in the pasture, light a fire, grill some food outdoors on the fire pit, or head inside and use the stocked kitchen, relax in the cozy living room. Master Bathroom features a 2 person jacuzzi, adjoins master bedroom with a Queen-size bed. Bedroom 2 has 2 single beds, #3 has 1 double.

Guest favourite
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, 143 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)

Top guest favourite
A spacious outdoor deck features a hot tub with surrounding wicker seating. A grill stands nearby, and comfortable lounge chairs are arranged for relaxation. Windows of the upper floor provide natural light while trees create a serene backdrop.
Cabin in Millmont
4.98 out of 5 average rating, 219 reviews

3BR Cozy Country Cabin w/ Hot Tub near Penns Creek

Bring the whole family to this spacious country cabin with a hot tub and lots of room for fun. The property is located .2 miles from the wide branch of Penns creek, an excellent trout stream for wild and stocked brown trout and rainbows. Also, perfect for canoeing, kayaking, fishing, and tubing! Close to numerous hiking trails and nature adventures. Our 3 Bed, 2 Bath country home is newly renovated and perfect for large groups and gatherings! Just 50 minutes to Penn State and 30 to Bucknell.

Guest favourite
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, 414 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!

Top guest favourite
Treehouse in Liverpool
5 out of 5 average rating, 11 reviews

TreeHouse Of Love*SwingBridge*Hottub*Ebikes*Nature

🌿 Treehouse of Love - A Romantic Couples Retreat - We Look Forward To Hosting You! THE MISSION *Escape the busyness of life and reconnect with the one you love at Treehouse of Love—a one-of-a-kind luxury treehouse nestled high among the trees and surrounded by the peaceful beauty of the Pennsylvania countryside. Whether you're celebrating an anniversary, honeymoon, birthday, or simply looking for a quiet getaway, this romantic retreat was thoughtfully designed for two. *HOTTUB *EBIKES

Guest favourite
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
4.94 out of 5 average rating, 159 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!

Top guest favourite
The exterior of a newly renovated duplex is presented, framed by lush green grass and trees. The front showcases warm lights emanating from large windows, creating a welcoming glow. The structure features a mix of traditional and modern design against a backdrop of cloudy skies.
Home in Lewisburg
5 out of 5 average rating, 109 reviews

Sleepy Hollow Lane in Lewisburg

This beautiful newly renovated 2-unit duplex is perfect for a family getaway or a friend's trip. This property is nestled in a quiet corner of the Buffalo Valley, in a rural country setting and back a long driveway, yet close to lots of places of interest. The setting is beautiful and private. You'll love the restful view of fields and sky, and watching the sunset from the back deck. The long-term residents living on the other side of the duplex are a friendly, retired couple.

Guest favourite
The cottage displays a welcoming exterior with a green metal roof and wooden siding. Stone pillars support the covered porch, which is adorned with warm lighting. A flag is displayed on the porch, and the surrounding landscape features large rocks and minimal landscaping.
Cabin in Mifflinburg
4.94 out of 5 average rating, 117 reviews

Charming Cottage, Water Views! Access to Creek!

This open concept cottage is the most well appointed rental along the famous Penns Creek. It features 3 bedrooms - downstairs bedroom is a traditional enclosed room, 2 upstairs bedrooms are unique open loft spaces that are visible to each other. A room separating curtain is there for privacy. There's the convenience of two baths with a lovely claw foot soaker tub. The cottage has 180 degree views of Penns Creek and private creek access and firepit about 100 steps away.

Guest favourite
Home in Middleburg
5 out of 5 average rating, 9 reviews

Ole' Yello ~steps from winery

Get comfortable and enjoy plenty of extra room at this spacious traditional farmhouse with modern aesthetics. Recently renovated with new furniture, appliances, and bedding. This rental features a fully stocked kitchen including farm-fresh eggs when available: dishwasher, Keurig, and microwave. Indoor electric fireplaces. Family games. Full bath with clawfoot tub and walk in shower on the second floor. Essentials included. Onsite parking for 4 vehicles. Heat and AC.

Top guest favourite
A modern cottage is nestled among trees, featuring a white exterior and contrasting dark roof. An outdoor patio with string lights provides a seating area, surrounded by natural stone landscaping and large rocks. The inviting structure exudes a serene charm, perfect for relaxation.
Home in Newport
4.99 out of 5 average rating, 452 reviews

Long Acre Farm Stay! Find seclusion on the back 40

Hi! Long Acre Hideaway is a secluded cottage dedicated to providing a quiet place for couples and/or small families to spend quality time with each other and with God. Come to the “back 40” of the farm to relax and rejuvenate! Experience some of the area’s best views on the walk around the perimeter of the farm on a 1.8 mile marked trail! Rest on the deck with a cup of coffee and watch for wildlife or soak in the private hot tub at night and watch the stars!

Guest favourite
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, 222 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

Top guest favourite
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
4.97 out of 5 average rating, 238 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.

Popular amenities for Kissimmee holiday rentals

  1. Airbnb
  2. United States
  3. Pennsylvania
  4. Snyder County
  5. Kissimmee