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Guesthouse vacation rentals in Kissimmee

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouses in Kissimmee

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

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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 Orlando
4.91 out of 5 average rating, 274 reviews

Modern Guest Studio (Private) Pool / Spa available

Private Guest Studio (Not Shared ) 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. Pool & Spa available (Not Shared) 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.

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
4.82 out of 5 average rating, 584 reviews

Spacious getaway close to Universal and Outlets!

PLEASE READ BEFORE BOOKING Checkin -4pm Checkout-10am Welcome to our home! The home is a basement apartment with private entrance ,driveway for one car, and one bedroom in your suite with 2 queen size beds, sofa pull out,and kitchen (portable burners NO STOVE) and a large bathroom with double shower head. This is your own space we have zero way to interact with you but we are a family who lives above you similar to neighbors in apartment. 5 min- universal 10 min- outlets 20 min- Disney

Guest favourite
Guesthouse in Kissimmee
4.91 out of 5 average rating, 139 reviews

Entire Deluxe studio for 2 near Disney&parks

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. I also offer the ride from/to the airport just for $30 each ride from home. 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

Top guest favourite
A cozy bedroom is showcased with warm wood paneling and soft lighting. A spacious bed is adorned with neutral tones and decorative pillows. A flat-screen TV is mounted on the wall, and large windows, covered by modern shades, allow filtered light to enter the room.
Guesthouse in Orlando
4.78 out of 5 average rating, 545 reviews

Private Studio Near Universal, Disney & Shopping!

Discover this cozy studio, completely private with its own entrance. It features a comfortable queen bed, a private bathroom, and a kitchen. It also includes a Luxurious Sofa and free parking. Just 15 minutes from Florida Mall, 15 minutes from the airport, 20 minutes from Disney, and 12 minutes from Universal Studios, as well as 8 minutes from I-Drive Orlando, Millenia Mall, and many more attractions. Perfect for a comfortable and private stay near Orlando’s top attractions!

Superhost
A comfortable bedroom is shown, featuring a spacious bed dressed in crisp linens. A flat-screen TV is mounted on the wall, while natural light enters through a window adorned with white blinds. Additional storage is provided by a nearby basket and a sleek side table.
Guesthouse in Orlando
4.8 out of 5 average rating, 253 reviews

Luxury 5 star home 3 min Universal/ Orlando City

Discover your home away from home in this inviting 1 bedroom, 1 bathroom guesthouse, designed for comfort and modern convenience. Relax in a prime location, this cozy retreat offers easy access to popular theme parks, making it an ideal choice for fun-filled vacations. The bathroom suite has a rain shower just like you would expect in a 5-star Hotel, full kitchen, appliances and 2 TVs, one in the bedroom, and another in the living room.

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, 494 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.

Guest favourite
The modern kitchen features a spacious island with seating for four. A vibrant yellow door adds a pop of color to the neutral decor. Stainless steel appliances and pendant lighting enhance the contemporary design, complemented by white tile backsplash and wooden accents.
Guesthouse in Orlando
4.93 out of 5 average rating, 321 reviews

CLEAN & Modern 2BR w/ sunny yard, close to Disney

Our place is a 2BR, one-bath entire home, with a cozy fire pit and patio furniture space, a fun kids playground area, and a large sunny yard with mature trees for you and guests to explore and enjoy. Excellent location within 15 mins driving distance to the main Disney amusement parks. Free WiFi and HDTV with streaming services available. Please read “Guest Access” for note on other house in the property.

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 Southern Oaks
4.84 out of 5 average rating, 108 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.

Top guest favourite
A modern living area features a gray sofa adorned with turquoise accent pillows, positioned beside a low black coffee table. A large area rug with abstract patterns covers the floor. The open kitchen and dining area are visible in the background, showcasing a stylish design.
Guesthouse in Kissimmee
4.98 out of 5 average rating, 281 reviews

"Little Blue House" Getaway Near the Disney Parks

Your home away from home! Enjoy a comfortable and relaxing stay in our Casa Azul. Spacious and modern, it features a bedroom with a double bed, a private bathroom, a living room with a sofa bed, a dining room, and a fully equipped kitchen. Ideal for vacations with family or friends.

Superhost
A modern kitchen area features white cabinetry with brass knobs and open shelving that displays decorative items. Stainless steel appliances, including a refrigerator and microwave, are visible. A coffee maker and cooking utensils are arranged on the countertop, contributing to a functional cooking space.
Guesthouse in Orlando
4.86 out of 5 average rating, 110 reviews

Great place to stay in Orlando!

Casa particular with exceptional location in the City of Orlando - Florida📍 The house has a smart front door, kitchen and bathrooms, accessories equipped with everything you need! It also has completely free parking. Minutes from Orlando and Universal water parks!

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
4.95 out of 5 average rating, 192 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.

Guest favourite
A small outdoor seating area features two chairs with tropical-themed cushions and a metal table between them. A green decorative flower hangs on the wall, and the tiled floor reflects a light color. A door is positioned nearby, leading to the interior.
Guesthouse in Orlando
4.77 out of 5 average rating, 622 reviews

Little Studio, Small studio.

This small studio is located on the side of the house. It has a separate entrance with easy access. The second door is the entrance to your studio. It has a small window.

Popular amenities for Kissimmee guesthouses

Quick stats about guesthouse rentals in Kissimmee

  • Total rentals

    40 properties

  • Nightly prices starting at

    $42 CAD before taxes and fees

  • Total number of reviews

    1.7K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Osceola County
  5. Kissimmee
  6. Guesthouse rentals