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

Total vacation rentals
Explore 40 vacation rentals in Kissimmee

Nightly prices starting at
Kissimmee vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

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

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Kissimmee vacation 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 guesthouse rentals in Kissimmee
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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.

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

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, centrally located, 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. 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.

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.

Beauty & Beast Guest House, Near Disney, Sleeps 4
Magical Beauty & the Beast guest house with 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!

"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.

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!

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.
Popular amenities for Kissimmee guesthouse rentals
Family-friendly guest house rentals

Magic Stay Cozy Studio near Disney & Universal

Couples Retreat! Private Guesthouse Near Disney

Cozy private studio • Near Epic and MCO

Next to Universal & Disney • Cozy 2BR Guesthouse

Disney / Orlando Guest House

Guest Home_ Orlando Airport and Disney

Comfy home away from home!

Nature Kissed Casita. Embrace the chill!
Guest house rentals with a patio

Privatepool studio near Disney Restaurants & Shops

Inviting 3 br haven: vaca/work

~ Luxe Modern Suite • Heated Pool • 2BR Gem

King-size Studio 4 min to Universal

Private 2BR Guesthouse + Pool-Heart of Kissimmee!

Thousand Oaks Peaceful Studio with Private Pool

El Patio Escape • Cozy Suite | Universal 15 minutes

Cozy Guest House Near MCO & Theme Parks
Guest house rentals with a washer and dryer

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

Lakeside Palm Escape

Cozy Lake View Stay

Relax & Recharge in the Heart of Orlando

Beautiful room for couples

MR 2 - Comfort and Privacy

Studio Private Guesthouse w Laundry!

Steps from the Magic World! The best accomodation!
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 268 | ﺩ.ﺇ 264 | ﺩ.ﺇ 268 | ﺩ.ﺇ 257 | ﺩ.ﺇ 257 | ﺩ.ﺇ 261 | ﺩ.ﺇ 264 | ﺩ.ﺇ 250 | ﺩ.ﺇ 242 | ﺩ.ﺇ 242 | ﺩ.ﺇ 253 | ﺩ.ﺇ 264 |
| 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 |
Destinations to explore
- Miami Vacation rentals
- Four Corners Vacation rentals
- Orlando Vacation rentals
- Miami Beach Vacation rentals
- Tampa Vacation rentals
- Fort Lauderdale Vacation rentals
- Savannah Vacation rentals
- Hollywood Vacation rentals
- Jacksonville Vacation rentals
- St. Augustine Vacation rentals
- Hilton Head Island Vacation rentals
- Key West Vacation rentals
- Rentals with an accessible height toilet Kissimmee
- Rentals with a home theater Kissimmee
- Family-friendly rentals Kissimmee
- Mansion rentals Kissimmee
- Rentals with a washer and dryer Kissimmee
- Rentals with an accessible height bed Kissimmee
- Rentals with lake access Kissimmee
- Beachfront rentals Kissimmee
- Rentals with a sauna Kissimmee
- Lakehouse rentals Kissimmee
- Rentals with breakfast Kissimmee
- Resort rentals Kissimmee
- Cottage rentals Kissimmee
- Rentals with pools Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Waterfront rentals Kissimmee
- Rentals with a fire pit Kissimmee
- Townhouse rentals Kissimmee
- Villa rentals Kissimmee
- Beach house rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Rentals with a kayak Kissimmee
- Rentals with an EV charger Kissimmee
- Apartment rentals Kissimmee
- Cabin rentals Kissimmee
- House rentals Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Rentals with beach access Kissimmee
- Fitness-friendly rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Hotel rooms Kissimmee
- Rentals with a fireplace Kissimmee
- Serviced apartment rentals Kissimmee
- Rentals with outdoor seating Kissimmee
- Tiny house rentals Kissimmee
- Vacation home rentals Kissimmee
- Private suite rentals Kissimmee
- Condo rentals Kissimmee
- Guesthouse rentals Osceola County
- Guesthouse rentals Florida
- Guesthouse rentals United States
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Camping World Stadium
- Epcot
- Universal's Volcano Bay
- Kia Center
- Disney's Animal Kingdom Theme Park
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- University of Central Florida
- Old Town
- ESPN Wide World of Sports
- LEGOLAND Florida Resort
- Disney's Hollywood Studios
- Aquatica
- ICON Park
- Tinker Field
- ChampionsGate Golf Club







