
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 $43 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
FamilyValueCleanliness

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
ValueLocationCheck-in

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.
LocationValueWi-Fi

Cosy studio with a private entrance near Epic
This place has a perfect strategic location: it will be very easy to plan your visit! In addition to being just 4 minutes from Orlando Airport and 3 minutes from the new EPIC Disney park, Disney parks are 18 minutes away It's a quiet and excellent place to work and also a great option to spend quality time with your partner You have shops and markets to buy food just 2 minutes away, this is an extraordinary option to spend your vacation🤗
FamilyValueBeach

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.
ValueFamilyTV

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
FamilyLocationWalkability

Beautiful brand new apartment
Disfruta de la sencillez de este alojamiento tranquilo, céntrico y acogedor . Es un apartamento espectacular tipo estudio con entrada independiente a la casa . Y todo el alojamiento está disponible solo para los huéspedes . A 15 min del aeropuerto de orlando y 20 min de los parques . Cerca de los outlets y del convención center. Contamos con estacionamiento y si deseas traslado también podríamos ayudarte
ValueLocationHospitality

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
FamilyValueBathroom

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.
FamilyValueCheckout

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!
ValueFamilyQuiet

"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.
ValueFamilyAccess

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!
ValueLocationLong stay
Popular amenities for Kissimmee guesthouses
Family-Friendly guesthouses

Magic Stay Cozy Studio near Disney & Universal
ComfortIndoor spacesHospitality

Upstairs cottage room by airport
LocationValueIndoor spaces

Couples Retreat! Private Guesthouse Near Disney
LocationBathroomLong stay

Luxury Anexo
LocationAccuracyHospitality

Little Studio, Small studio.
FamilyLocationSolo travel

Disney / Orlando Guest House
FamilyValueHospitality

Guest Home_ Orlando Airport and Disney
LocationValueSolo travel

Nature Kissed Casita. Embrace the chill!
FamilyValueCondition
Guesthouses with a patio

Charming Lakeside small House
LocationFamilyBathroom

Privatepool studio near Disney Restaurants & Shops
ValueFamilyPool

Antilla Oasis – Private Guesthouse
LocationFamilyComfort

Inviting 3 br haven: vaca/work
FamilyLocationCleanliness

~ Luxe Modern Suite • Heated Pool • 2BR Gem
FamilyLocationBathroom

Private 2BR Guesthouse + Pool-Heart of Kissimmee!
ValueLocationCheck-in

Thousand Oaks Peaceful Studio with Private Pool
FamilyLocationEV charging

Cozy Guest House Near MCO & Theme Parks
LocationComfortCleanliness
Guest house rentals with a washing machine and dryer

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

Lakeside Palm Escape
LocationFamilyBathroom

Cozy Lake View Stay
ValueLocationCondition

Relax & Recharge in the Heart of Orlando
ValueLocationHot tub

Beautiful room for couples
ValueLocationComfort

Boutique Suite in Orlando
LocationValueCheck-in

Comfy home away from home!
FamilyLocationParks

MR 2 - Comfort and Privacy
ValueFamilyOutdoor spaces
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $104 AUD | $103 AUD | $104 AUD | $100 AUD | $100 AUD | $101 AUD | $103 AUD | $97 AUD | $94 AUD | $94 AUD | $98 AUD | $103 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
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Camping World Stadium
- Magic Kingdom Park
- 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
- ICON Park
- Aquatica
- ChampionsGate Golf Club
- Tinker Field







