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Guest house holiday rentals in Kissimmee

Find and book unique guest house rentals on Airbnb

Top-rated guest house rentals in Kissimmee

Guests agree: these guest house rentals 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.
Guest house in Orlando
4.9 out of 5 average rating, 282 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.

Superhost
Guest house in Wadeview Park
4.85 out of 5 average rating, 333 reviews

Couples Oasis *Heated Pool* and Lake View

Have a romantic getaway in this SODO Couples Oasis Retreat with private pool or come work alone in this peaceful oasis. Perfect for couples or the busy profesional who want privacy and quiet with lake view while relaxing by the pool. Centrally located in SODO by downtown Orlando. Close to everything. Walk to great nearby eating places. Love ice cream Kelly’s Hand Made ice cream is a 5 minute walk from the house. *Heated Pool* available for $20 fee for first day and $10 every extra day.

Guest favourite
Guest house in Kissimmee
4.9 out of 5 average rating, 153 reviews

Cozy&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

Guest favourite
A garden cottage is nestled among vibrant yellow flowers and lush greenery. A small patio table with chairs invites outdoor relaxation, while a large tree provides shade. The cottage's entrance is framed by blooming plants, creating a serene environment for guests.
Guest house in Wadeview Park
4.86 out of 5 average rating, 426 reviews

Garden Cottage Efficiency

Relax in this newly interior renovated private garden cottage. Featuring a beautiful tropical garden, private entrance, full kitchen/bath, queen-size bed (additional single option), free 1 off street parking spot, WiFi, TV. Sheets, towels, blankets, kitchenware and toiletries provided. You may enjoy the patio and covered gazebo. Secure private access 24/7 Shopping, dining and recreation are less than a five-minute walk. Located between downtown and the attractions. LGBT friendly.

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.
Guest house in Four Corners
4.98 out of 5 average rating, 510 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.

Top 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.
Guest house in Orlando
4.93 out of 5 average rating, 336 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.
Guest house in Southern Oaks
4.85 out of 5 average rating, 114 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 spacious bed is dressed in a patterned duvet with a combination of navy and white colors. Soft coral pillows add a pop of color. A small nightstand is positioned beside it, featuring a unique lamp. The room is softly illuminated, creating a cozy ambiance.
Guest house in Kissimmee
4.94 out of 5 average rating, 140 reviews

Beautiful brand new apartment

Enjoy the simplicity of this quiet, central and cozy place to stay. It is a spectacular studio apartment with a separate entrance to the house. And the entire home is available only to guests. With a grill area. 15 minutes from the Orlando airport and 20 minutes from the parks. Close to the outlets and the convention center. Parking is available and if you want transportation we can also help you

Top guest favourite
Guest house in Kissimmee
4.99 out of 5 average rating, 109 reviews

Make a reservation in a unforgettable a cozy place

Casa Venice, acogedora, ideal para pasar una corta estancia o tener unas vacaciones inolvidables en Kissimmee, cerca a las mejores atracciones turísticas, restaurantes y parques naturales Clean, quiet 30 minutes to Disney parks, Old Town, lots of great food locations near by. 9m walmart, 7m Aldi 7m Ross, and more Safe and secure entrance. privateparking

Top guest favourite
The spacious studio features a king bed with light bedding, a ceiling fan, and natural light from side windows. A 70-inch TV is positioned on a media stand across from the bed. A cozy seating area includes a circular coffee table and a decorative pouf.
Guest house in Wadeview Park
4.93 out of 5 average rating, 116 reviews

Chic, luxury escape near Disney Universal & Epic

Welcome to your perfect Orlando retreat! Our newly built guesthouse combines modern luxury with a cozy charm, offering a beautifully decorated, spacious haven designed to make your stay unforgettable. With elegant finishes and stylish decor, this clean guesthouse provides the ultimate in comfort and sophistication.

Top guest favourite
Guest house in Kissimmee
4.98 out of 5 average rating, 309 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.

Guest favourite
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.
Guest house in Orlando
4.86 out of 5 average rating, 125 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!

Popular amenities for guest house rentals in Kissimmee

When is the best time to visit Kissimmee?

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Quick stats about guest house rentals in Kissimmee

  • Total holiday rentals

    Explore 40 holiday rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,010 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 of Kissimmee holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Kissimmee rentals

  • 4.8 Average rating

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

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