
Guesthouse vacation rentals in Kissimmee
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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

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.

Cozy 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🤗

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

Beautiful brand new apartment
Enjoy the simplicity of this quiet, central and cozy accommodation. It is a spectacular studio apartment with a separate entrance to the house. And the entire accommodation is available only to guests. 15 minutes from Orlando Airport and 20 minutes from the parks. Close to the outlets and the convention centre. We have parking, 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!
Popular amenities for Kissimmee guesthouses
Family-friendly guesthouses

Magic Stay Cozy Studio near Disney & Universal

Luxury Anexo

Next to Universal & Disney • Cozy 2BR Guesthouse

Little Studio, Small studio.

Disney / Orlando Guest House

Guest Home_ Orlando Airport and Disney

Comfy home away from home!

Steps from the Magic World! The best accomodation!
Guesthouses with a patio

Privatepool studio near Disney Restaurants & Shops

~ Luxe Modern Suite • Heated Pool • 2BR Gem

Spacious XL Camper 15 minutes from Disney world.

Private 2BR Guesthouse + Pool-Heart of Kissimmee!

The Little House

Cozy Guest House Near MCO & Theme Parks

Beautiful room for couples

Boho Boutique • Double Shower & Patio | MCO 10 min
Guesthouse 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

Kyle's Place - Private Unit, Pool + Laundry Room

A place with a view

Modern & Cozy Retreat - Orlando City Center Epic

MR 2 - Comfort and Privacy
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $102 CAD | $101 CAD | $102 CAD | $98 CAD | $98 CAD | $99 CAD | $101 CAD | $95 CAD | $92 CAD | $92 CAD | $97 CAD | $101 CAD |
| 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 |
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 $42 CAD 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

Wifi availability
40 of Kissimmee vacation 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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- 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







