
Guest house holiday rentals in Kissimmee
Find and book unique guest house rentals on Airbnb
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 $39 SGD 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

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!
Top-rated guest house rentals in Kissimmee
Guests agree: these guest house 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

Bello apartamento a estrenar
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

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.

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.

Estupendo alojamiento en Orlando!
Casa particular con ubicación excepcional en la ciudad de Orlando - Florida📍 La casa cuenta con puerta principal inteligente, cocina y baños complementos equipados con todo lo que necesitas! Además cuenta con estacionamiento completamente gratis. A tan solo minutos de parques acuáticos de Orlando y Universal!

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.

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 guest house rentals in Kissimmee
Family-friendly guest house rentals

Magic Stay Cozy Studio near Disney & Universal

Couples Retreat! Private Guesthouse Near Disney

Acogedor estudio privado•Cerca de Epic y 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 min

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

Hermosa habitación para pareja

MR 2 - Conforto e Privacidade

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 | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $95 SGD | $93 SGD | $95 SGD | $91 SGD | $91 SGD | $92 SGD | $93 SGD | $88 SGD | $86 SGD | $86 SGD | $90 SGD | $93 SGD |
| 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 Holiday rentals
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- Orlando Holiday rentals
- Miami Beach Holiday rentals
- Tampa Holiday rentals
- Fort Lauderdale Holiday rentals
- Savannah Holiday rentals
- Hollywood Holiday rentals
- Jacksonville Holiday rentals
- St. Augustine Holiday rentals
- Hilton Head Island Holiday rentals
- Key West Holiday rentals
- Rentals with a cinema Kissimmee
- Family-friendly rentals Kissimmee
- Rentals with a sauna Kissimmee
- Rentals with breakfast Kissimmee
- Rentals with pools Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Waterfront rentals Kissimmee
- Rentals with a kayak Kissimmee
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- Serviced apartment rentals Kissimmee
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- Private suite rentals Kissimmee
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- Rentals with an accessible-height bed Kissimmee
- Rentals with lake access Kissimmee
- Rentals with an accessible-height toilet Kissimmee
- Cabin rentals Kissimmee
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- Rentals with a firepit Kissimmee
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- Tiny house rentals Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Cottage rentals Kissimmee
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- Fitness-friendly rentals Kissimmee
- Guest house rentals Osceola County
- Guest house rentals Florida
- Guest house 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







