
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.

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

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.

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

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

Beautiful brand new apartment
Enjoy the simplicity of this quiet, centrally located, and cozy place to stay. It is a spectacular studio apartment with a separate entrance to the house. And the entire home is available only to guests. 15 minutes from the Orlando airport and 20 minutes from the parks. Close to the outlets and the convention center. Parking is available, 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.
Popular amenities for Kissimmee guesthouse rentals
Family-friendly guest house rentals

Privatepool studio near Disney Restaurants & Shops

Upstairs cottage room by airport

Couples Retreat! Private Guesthouse Near Disney

Luxury Anexo

Thousand Oaks Peaceful Studio with Private Pool

Studio with kitchen , Full Privacy & Patio

Comfy home away from home!

Unique Studio Minutes From Disney & Universal
Guest house rentals with a patio

~ Luxe Modern Suite • Heated Pool • 2BR Gem

Lakeside Palm Escape

Private 2BR Guesthouse + Pool-Heart of Kissimmee!

The Little House

Cozy Guest House Near MCO & Theme Parks

Beautiful room for couples

MCO Boho Suite near Florida Mall & Hospitals

MR 1 - Comfort and Privacy
Guest house rentals with a washer and dryer

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

Cozy Lake View Stay

Relaxing Private Studio in the Trees!

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

A place with a view

Private Guesthouse | Yard & W/D | Downtown Orlando

Modern & Cozy Retreat - Orlando City Center Epic

The Cottage A Pet Friendly Guesthouse
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 268 | ﺩ.ﺇ 264 | ﺩ.ﺇ 268 | ﺩ.ﺇ 257 | ﺩ.ﺇ 257 | ﺩ.ﺇ 261 | ﺩ.ﺇ 264 | ﺩ.ﺇ 250 | ﺩ.ﺇ 242 | ﺩ.ﺇ 242 | ﺩ.ﺇ 253 | ﺩ.ﺇ 264 |
| 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.ﺇ 110 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

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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- Guesthouse rentals Osceola County
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- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Camping World Stadium
- Reunion Resort Golf Courses - Palmer & Watson
- Aquatica
- University of Central Florida
- ICON Park
- Disney's Hollywood Studios
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- ESPN Wide World of Sports







