
Guest house holiday rentals in Kissimmee
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Top-rated guest house rentals in Kissimmee
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

Modern 1950s Studio • Near Downtown & Theme Parks
Fully renovated 1950s studio (2024) in a safe, quiet Orlando neighborhood! Enjoy a plush queen bed, walk-in shower, Roku TV, and full kitchen with Keurig. Includes a private driveway, separate entrance, and cozy living area with stylish modern décor. In-unit washer and dryer for your convenience. Just 3 mi to downtown, 10 mi to Universal, 8 mi to the airport, and 18 mi to Disney—perfect for couples or solo travelers seeking comfort, privacy, and modern style in a peaceful setting.

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

Downtown private pool house. Two blocks from ORMC
Recharge in this private one bedroom, one bath pool house. Relax in the pool after a long day and enjoy a restful night in a very comfortable queen size bed. Walking distance to downtown, ORMC, and the Dr. Phillips Performing Arts Center. Two miles to Kia (Amway) Center for concerts and the Orlando Magic. Two miles to the Orlando City and Pride Soccer stadium. Three miles to Camping World Stadium. Nine miles to Universal Studios. 14 miles to SeaWorld. 15 miles to Disney.

Luxury Guesthouse | Private Yard & Patio | Orlando
✔ Fully detached private guesthouse — no shared walls ✔ Fully fenced front & back yard — your own outdoor oasis ✔ Private patio seats 4 — perfect for morning coffee or evening drinks ✔ Full kitchen — fridge, stove, microwave & coffee maker ✔ Queen bed + queen sofa bed — sleeps 4 comfortably ✔ Washer & dryer in unit ✔ 65" Smart TV — Netflix, Hulu, Disney+ & HBO Max ✔ Dedicated workspace ✔ High-speed WiFi ✔ Two private parking spots ✔ All essentials provided

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

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

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!

"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

Privatepool studio near Disney Restaurants & Shops

Magic Stay Cozy Studio near Disney & Universal

Acogedor estudio con entrada privada cerca de Epic

Little Studio,Pequeño estudio .

Disney / Orlando Guest House

Paradise nook near Orlando's theme parks

Hermosa habitación para pareja

Guest Home_ Orlando Airport and Disney
Guest house rentals with a patio

~ Luxe Modern Suite • Heated Pool • 2BR Gem

Lakeside Palm Escape

King-size Studio 4 min to Universal

Private 2BR Guesthouse + Pool-Heart of Kissimmee!

Cozy Guest House Near MCO & Theme Parks

Cozy Guest Suite in heart of Downtown Orlando

Historic lakefront guesthouse

MR 2 - Conforto e Privacidade
Guest house rentals with a washing machine and dryer

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

Cozy Lake View Stay

Relaxing Private Studio in the Trees!

A place with a view

Beauty & Beast Guest House, Near Disney, Sleeps 4

Modern & Cozy Retreat - Orlando City Center Epic

The Cottage A Pet Friendly Guesthouse

1/1 Private Guesthouse in Orlando (South Downtown)
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $94 SGD | $92 SGD | $94 SGD | $90 SGD | $90 SGD | $91 SGD | $92 SGD | $87 SGD | $85 SGD | $85 SGD | $88 SGD | $92 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 |
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 $38 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!
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- Guest house rentals Osceola County
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- 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
- 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







