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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 $51 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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Guest favourite
Guesthouse in Winter Garden
4.9 out of 5 average rating, 107 reviews

A place with a view

Welcome to Your Secluded Getaway Enjoy a quiet retreat minutes from supermarkets and Florida’s top attractions. Urgent care , Emergency room & Hospital are all nearby Top Attractions Island H2O: 23m | Epcot: 27m | SeaWorld: 32m Disney Springs: 34m | Universal: 36m Legoland: 1h | Busch Gardens: 1h 27m Shopping & Dining Winter Garden/Clermont14m Outlets 28m | Florida Mall 35m | I-Drive 40m Travel MCO Airport 40m Oversized Parking: Dedicated space for boats, RVs, and moving trucks. storage only

FamilyLocationShared spaces

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
4.9 out of 5 average rating, 198 reviews

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

ValueLocationAmenities

Guest favourite
An outdoor pool is centered within a landscaped patio area, surrounded by lush greenery and mature plants. Two teak lounge chairs are positioned in the foreground, facing the calm water, while sun umbrellas and vibrant seating are visible nearby.
Guesthouse in Orlando
4.9 out of 5 average rating, 178 reviews

Vintage Florida Vibes House

Enjoy a peaceful & stylish getaway in this detached Guesthouse with private entrance, gardens, kitchen & pool. Sip coffee in the shade of our Oak trees. Grill out while you watch TV and cool off in the pool after a day at the parks. Sit under the stars and string lights and nestle into your cozy beds, with your own dedicated central AC unit and ceiling fans to keep you comfortable. Only 2 miles from downtown Orlando and directly off the I4 highway that takes you to every park & attraction.

ValueFamilyGetting around

Top Guest favourite
Guesthouse in Kissimmee
4.98 out of 5 average rating, 351 reviews

"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.

LocationValueIndoor spaces

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
4.9 out of 5 average rating, 291 reviews

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.

LocationFamilyWi-Fi

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
4.98 out of 5 average rating, 536 reviews

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.

FamilyLocationCleanliness

Guest favourite
Guesthouse in Kissimmee
4.91 out of 5 average rating, 169 reviews

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

FamilyLocationGetting around

Guest favourite
A bright living area is presented with vaulted ceilings and hardwood floors. Comfortable seating is arranged around a central coffee table, with soft lighting provided by table lamps. Natural light filters through the windows, illuminating the decor and creating a welcoming atmosphere.
Guesthouse in Orlando
4.86 out of 5 average rating, 126 reviews

Historic lakefront guesthouse

Relax and enjoy the serenity of this historic guesthouse with large grounds and a beautiful lake. Start out your day with a cup of your favorite coffee out on the balcony or shoreside, watching the sun reflect off the lake and listening to nature. Then take out a kayak or paddle board for a bit of cardio before heading out to the parks, or enjoy some of Orlando’s hidden secrets for a bit of local fun.

LocationValueNearby

Top Guest favourite
Guesthouse in Buenaventura Lakes
4.99 out of 5 average rating, 125 reviews

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

ValueFamilyCheck-in

Top Guest favourite
Guesthouse in Orlando
4.99 out of 5 average rating, 121 reviews

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.

LocationFamilySleep quality

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
4.93 out of 5 average rating, 104 reviews

Beauty & Beast Theme, Near Disney world, 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!

LocationValueDecor

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
4.94 out of 5 average rating, 228 reviews

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.

ValueLocationIndoor spaces

Popular amenities for Kissimmee guesthouses

When is the best time to visit Kissimmee?

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Avg. price$124 NZD$122 NZD$124 NZD$121 NZD$116 NZD$117 NZD$122 NZD$116 NZD$112 NZD$112 NZD$117 NZD$122 NZD
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Destinations to explore