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Guesthouse holiday rentals in Kissimmee

Find and book unique guesthouse rentals on Airbnb

Quick stats about guesthouse rentals in Kissimmee

  • Total holiday rentals

    Explore 50 holiday rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee holiday rentals start at $52 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,480 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Kissimmee holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Kissimmee rentals

  • 4.8 Average rating

    Kissimmee stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated Guesthouses in Kissimmee

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Top Guest favourite
Guesthouse in Oak Ridge

Cozy Private Studio Near Universal & Disney

Enjoy a cozy, completely private studio with its own entrance, a comfortable queen bed, private bathroom, kitchenette, luxurious sofa, and free parking. Conveniently located just 8 minutes from I-Drive and Millenia Mall, 12 minutes from Universal Studios, 15 minutes from Orlando International Airport and Florida Mall, and 20 minutes from Disney. Perfect for couples or solo travelers seeking comfort, privacy, and easy access to Orlando’s top attractions, restaurants, shopping, and entertainment!

4.8 out of 5 average rating, 619 reviews
Guest favourite
A cozy living area features a dark gray sofa with bright yellow accent pillows and a matching ottoman. There are two wooden side tables with potted plants placed on them, and a wall art piece displaying the word 'FAMILY' hangs above.
Guesthouse in Orlando

Spacious getaway close to Universal and Outlets!

Cozy private basement apartment in the heart of Orlando (32819), just 1 mile from Universal Studios. Private entrance, driveway parking for one car, and your own AC. Includes 1 bedroom with 2 queen beds, sofa pull-out, kitchenette (portable burners, no stove), and large bathroom with double shower head. Small patio available for guests. Family lives upstairs—similar to apartment living yet we have no contact or shared spaces. Check-in 4PM / Check-out 10AM. 10 min to outlets, 20 min to Disney.

4.82 out of 5 average rating, 643 reviews
Guest favourite
A spacious studio contains a king-size bed with a light-colored quilt, flanked by two bedside lamps. A small refrigerator and kitchenette are visible in the corner, while a ceiling fan provides airflow. Windows are adorned with light curtains, allowing natural light into the room.
Guesthouse in Orlando

King-size Studio 4 min to Universal

Amazing location! king-size private studio, perfectly situated in the desirable Dr. Phillips area, You'll be just 4 minutes from the excitement of Universal Studios and CityWalk. "Restaurant Row," home to some of Orlando’s finest dining only 7 minutes away. The Orlando Convention Center is a quick 10-minute drive, MCO Airport is about 20 minutes away, and Disney is just 18 minutes from your doorstep. Newly remodeled bathroom, a convenient kitchenette, a fridge, a microwave, and a 65-inch TV

4.9 out of 5 average rating, 201 reviews
Top Guest favourite
Guesthouse in Kissimmee

"Little Blue House" Getaway Near the Disney Parks

"Blue House" , Your Home Away from Home! Enjoy a comfortable and relaxing stay in our cozy Blue House. This completely independent accommodation features a bedroom with a Queen bed, private bathroom, living room with a sofa bed, dining area, and fully equipped kitchen. One designated parking space is included for 1 vehicle only. The vehicle must be parked only in the designated Blue House parking space. Parking on the grass or on the neighboring property is not permitted.

4.98 out of 5 average rating, 353 reviews
Superhost
An open kitchen area features modern appliances, including a stainless steel refrigerator and stacked washer/dryer units. A round dining table surrounded by black chairs is illuminated by a decorative light fixture. A wall-mounted TV sits across from the dining space, enhancing practicality.
Guesthouse in Bay Hill

Modern Guest Studio with pool access

Private Guest Studio in a Perfect Orlando location, 5 minutes from I-Drive, Universal Studios, Disney World & Premium Shopping Outlets. Very Quiet lovely neighborhood with Biking distance to "Restaurant Row" where all your favorite restaurants are located. All major highways at your finger tips / ride 15 min to Disney! This space has an industrial modern look with high ceilings, Stay and cook with all the amenities including a Washer and Dryer.

4.9 out of 5 average rating, 291 reviews
Top Guest favourite
A cozy bedroom features a tufted gray headboard above a neatly made bed with white linens. Decorative pillows are arranged on the bed, and whimsical letters spelling 'DREAM' adorn the wall above. Two bedside tables with lamps provide a soft glow.
Guesthouse in Four Corners

Quiet Room Close to Disney and Attractions

Quaint and quiet retreat just minutes from attractions. Private in-law suite and bathroom, detached from main house. Features all the basic amenities of a hotel room with the feeling of home. Room is perfect for up to three persons. Queen bed and additional sleeper sofa. Located in Reunion Resort. There is a pool, gym, and spa located within the resort but not on the property and is for Reunion club members only.

4.98 out of 5 average rating, 538 reviews
Guest favourite
Guesthouse in Kissimmee

Charming Studio | Near Disney & Universal

Welcome to my independent apartment in my house, I have a great location and you can enjoy easy access to popular shops, restaurants and parks from this charming place to stay with a great location. MCO 30 Min Kissimmee gateway Airport 3 miles-7min Osceola hospital 2.7 miles-7min Disney world and Disney parks are 11-12 miles Universal Studios/ aventure Island is 18 miles The Loop Shopping center is 5.7 miles

4.9 out of 5 average rating, 170 reviews
Top Guest favourite
Guesthouse in Buenaventura Lakes

cozy Fully self-contained/ kitchen and bathroom

Casa Venice, cozy, ideal for a short stay or an unforgettable vacation in Kissimmee, close to the best tourist attractions, restaurants and natural parks Clean, quiet 30 minutes to Disney parks, Old Town, lots of great food locations nearby. 9 minutes to Walmart, 7 minutes to Aldi 7 minutes to Ross, and more Safe and secure entrance. Private parking

4.99 out of 5 average rating, 126 reviews
Guest favourite
Guesthouse in Doctor Phillips

Universal Getaway Private Guesthouse + Kitchen

Your comfortable, modern Orlando home away from home is just 3 minutes from Universal and minutes from Epic Universe, Disney, SeaWorld, dining, and shopping. This private 1-bedroom guesthouse features a full kitchen, private entrance, cozy living space, and dedicated parking — perfect for couples, solo travelers, business travelers, or small families.

4.8 out of 5 average rating, 280 reviews
Top Guest favourite
Guesthouse in Orlando

Beautiful garage suite w/washer and dryer

Enjoy a peaceful, centrally-located garage suite in Southwest Orlando—perfect for convention goers! Just 15 minutes from the airport, and Universal theme parks, 25 min drive to Disney theme parks , 10 min to Sea World and only a 20-minute walk to the JW Marriott and Ritz Carlton. Washer and dryer inside of the unit.

4.99 out of 5 average rating, 122 reviews
Guest favourite
A cozy sleeping area is highlighted by a vibrant yellow bedspread. Decorative pillows in shades of blue and red accent the bed, complemented by a colorful wall art piece overhead. A stylish blue chair with a red pillow is positioned to the side, alongside a doorway.
Guesthouse in Davenport

Near Disney world, Beauty & Beast Theme, Sleeps 4

Magical Beauty & the Beast guest House with a queen bed + hidden pull-out Twin XL, sofa bed, themed decor, coffee bar, and in-suite washer/dryer. Quiet cul-de-sac location near Disney & Orlando theme parks. Perfect for families, couples, or small groups seeking comfort, convenience, and a magical stay!

4.93 out of 5 average rating, 104 reviews
Top Guest favourite
A well-equipped kitchen is visible, featuring modern cabinetry and stainless steel appliances. A small dining table is positioned in the foreground, adorned with a vase of fresh flowers. The backsplash adds a touch of elegance, complementing the overall clean and bright design.
Guesthouse in Clermont

Modern efficiency ~ Great location

Modern and very comfortable efficiency with private entrance, 1 free parking at driveway, equipped kitchen, 1 queen bed & 1 futon. Only 20 min drive to Magic Kingdom, 35 min to Universal, 25 min to Disney Springs and close to many other attractions.

4.94 out of 5 average rating, 229 reviews

Popular amenities for Kissimmee guesthouses

When is the best time to visit Kissimmee?

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Avg. price$127 NZD$126 NZD$127 NZD$124 NZD$119 NZD$120 NZD$126 NZD$119 NZD$115 NZD$115 NZD$120 NZD$126 NZD
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Destinations to explore