
Guesthouse vacation rentals in Kissimmee
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Top-rated guesthouse rentals in Kissimmee
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

Vintage Florida Vibes House
Enjoy a peaceful & stylish getaway in this detached Guesthouse with private entrance, gardens, kitchen & pool. Sip coffee in the shade of our Oak trees. Grill out while you watch TV and cool off in the pool after a day at the parks. Sit under the stars and string lights and nestle into your cozy beds, with your own dedicated central AC unit and ceiling fans to keep you comfortable. Only 2 miles from downtown Orlando and directly off the I4 highway that takes you to every park & attraction.

Couples Oasis *Heated Pool* and Lake View
Have a romantic getaway in this SODO Couples Oasis Retreat with private pool or come work alone in this peaceful oasis. Perfect for couples or the busy profesional who want privacy and quiet with lake view while relaxing by the pool. Centrally located in SODO by downtown Orlando. Close to everything. Walk to great nearby eating places. Love ice cream Kelly’s Hand Made ice cream is a 5 minute walk from the house. *Heated Pool* available for $20 fee for first day and $10 every extra day.

Cozy & Deluxe studio for 2 near Disney & parks
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. I also offer the ride from/to the airport just for $30 each ride from home. 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

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.

𝓜𝓸𝓭𝓮𝓻𝓷 𝕧𝕒𝕔𝕒𝕥𝕚𝕠𝕟 𝕚𝕟 𝕆𝕣𝕝𝕒𝕟𝕕𝕠
✔ 2022 built totally private detached guest house away from the main house ✔ Private two parking spots ✔ private front & back yard space ✔ Fully fenced for maximum privacy ✔ Private patio space in private backyard seats 4 people ✔ Comfortable Queen bed + Queen pull out sofa unit ✔ Full Kitchen ✔ Small back patio with chairs ✔ Smart TV ✔ Washer/Dryer FREE in unit ✔ Workspace ✔ High-Speed Wi-Fi ✔ Free Parking (2 spaces) ✔ All essentials included towels, shampoo, conditioner

The Cottage A Pet Friendly Guesthouse
Welcome to The Cottage! A pet friendly, super cute, and quiet studio apartment built in 2016, located above the detached garage behind my house. Pets always stay for free, and no additional cleaning fees are charged. Private self access is provided so you come and go as you please. The unit has a full kitchen, king sized bed, 4 pillows, 100% cotton sheets and coverlet. Laundry detergent and dish soap are provided. Trash is located on the west sideof the building.

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 . Con área de parrilla . 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

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.

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.

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 Kissimmee guesthouse rentals
Family-friendly guest house rentals

Privatepool studio near Disney Restaurants & Shops

Spectacular Relaxing Blue Moon-EPIC,OIA,Fl Mall

Luxury Anexo

Nice Brand New Studio !!

A place with a view

“Orlando private Cozy suite”

BeachGuyDave's Reunion Guesthome

Modern & Cozy Studio|Private Retreat w Kitchenette
Guest house rentals with a patio

Modern and cozy Studio in the heart of Orlando

Lakeside Palm Escape

Thousand Oaks Peaceful Studio with Private Pool

La Casita

Orlando Private Tiny Guest House

Nature Escape

Sage Guest House

Guest Home| Orlando Airport & Florida Mall 15 Min
Guest house rentals with a washer and dryer

Cozy Lake View Stay

Relaxing Private Studio in the Trees!

Modern & Cozy Retreat - Orlando City Center Epic

Boutique Suite in Orlando

Modern Guest Studio (Private) Pool / Spa available

1/1 Private Guesthouse in Orlando (South Downtown)

Cozy Guest Home 1.8 Miles from City Center

Winsome Farm Guest House
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ261 | ﺩ.ﺇ261 | ﺩ.ﺇ261 | ﺩ.ﺇ257 | ﺩ.ﺇ257 | ﺩ.ﺇ261 | ﺩ.ﺇ264 | ﺩ.ﺇ250 | ﺩ.ﺇ242 | ﺩ.ﺇ228 | ﺩ.ﺇ272 | ﺩ.ﺇ261 |
| 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 ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 2,010 verified reviews to help you choose

Rentals with dedicated workspaces
10 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!
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Give Kids the World Village
- Disney Springs
- Walt Disney World Resort Golf
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- ESPN Wide World of Sports
- Disney's Animal Kingdom Theme Park
- Epcot
- Old Town
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Discovery Cove
- Aquatica
- Bluegreen Vacations Fountains, Ascend Resort Collection
- Disney's Hollywood Studios
- Island H2O Live!
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club






