
Guesthouse holiday rentals in Kissimmee
Find and book unique guesthouse rentals on Airbnb
Quick stats about guesthouse rentals in Kissimmee

Total holiday rentals
Explore 40 holiday rentals in Kissimmee

Nightly prices starting at
Kissimmee holiday rentals start at $42 AUD per night before taxes and fees

Verified guest reviews
Over 2,370 verified reviews to help you choose

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, Wifi 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.

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

Spectacular Relaxing Blue Moon-EPIC,OIA,Fl Mall
Este lugar tiene una ubicación estratégica perfecta : ¡será muy fácil planear tu visita! Además que está a solo 4 minutos del Aeropuerto de Orlando y a 3 minutos del nuevo parque de Disney EPIC ,los parques de Disney están a 18 minutos Es un lugar tranquilo y excelente para trabajo y además de ser una magnífica opción para pasar tiempo de calidad que tu pareja Tienes tiendas y mercados para comprar comida a solo 2 minutos , esta es una extraordinaria opción para pasar tus vacaciones🤗

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. 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

Orlando Private Tiny Guest House
*Quiet, safe neighborhood Premium location *20 minutes to Orlando Airport *20 minutes to Disney parks & Disney Springs *25 minutes to Universal Studios & CityWalk *7 minutes to shopping plaza with top outlets and diverse dining *5 minutes to super Walmart *Local minimarkets. Inside your tiny home: *Queen-size bed *Coffee, fridge & microwave *Private entrance + patio *Modern shower *Air conditioning, Wi-Fi & Smart TV *Need transportation or special arrangements? Let us know

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.

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.

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.

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

Modern 1BR Guesthouse • Prime Orlando Location
Welcome to your comfortable and modern 1-bedroom guesthouse in a prime Orlando location! Just minutes from Universal, Disney, Epic Universe & local dining. Enjoy a full kitchen, cozy living space, and stylish design — perfect for couples, solo travelers, or small families. Relax after the parks or explore Orlando’s top attractions with ease. Your home away from home awaits!

cozy Fully self-contained/ kitchen and bathroom
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

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.

"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.
Popular amenities for Kissimmee guesthouses
Family-Friendly guesthouses

Upstairs cottage room by airport

Luxury Anexo

comfortable stay

A place with a view

Beauty & Beast Guest House, Near Disney, Sleeps 4

Comfy home away from home!

1/1 Private Guesthouse in Orlando (South Downtown)

Charming & Cozy Guest House Minutes from Disney
Guesthouses with a patio

Privatepool studio near Disney Restaurants & Shops

~ Luxe Modern Suite • Heated Pool • 2BR Gem

Lakeside Palm Escape

Private 2BR Guesthouse + Pool-Heart of Kissimmee!

Thousand Oaks Peaceful Studio with Private Pool

The Little House

Bright Boho Suite near MCO, Parks & ORMC • 6824

Unique Studio Minutes From Disney & Universal
Guest house rentals with a washing machine and dryer

Brand New Cozy Space - 15 Min From Disney & Shops.

Cozy Lake View Stay

Relax & Recharge in the Heart of Orlando

Cozy Lake Front Cottage

Modern & Cozy Retreat - Orlando City Center Epic

Beautiful room for couples

Boutique Suite in Orlando

Nature Escape
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $101 AUD | $100 AUD | $101 AUD | $97 AUD | $97 AUD | $99 AUD | $100 AUD | $94 AUD | $92 AUD | $92 AUD | $96 AUD | $100 AUD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
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- Guesthouse rentals Osceola County
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- Guesthouse rentals United States
- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Magic Kingdom Park
- Orlando / Kissimmee KOA
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- University of Central Florida
- ChampionsGate Golf Club







