
Guesthouse vacation rentals in Kissimmee
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouses in Kissimmee
Guests agree: these guesthouses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Kissimmee guesthouses
Family-friendly guesthouses

A place with a view

BeachGuyDave's Reunion Guesthome

Convenient Getaway Near Orlando Hotspots

Modern & Cozy Studio|Private Retreat w Kitchenette

Cozy Tiny house in Kissimmee close the parks

Magnolia Ranch - Comfort and Privacy

Guest Suite at Reunion Golf Resort close to Disney

Lakefront Guest House by downtown :Boat, Fishing…
Guesthouses with a patio

Private Pool Studio Close to Rest & Attractions

Modern and cozy Studio in the heart of Orlando

Lakeside Palm Escape

King-size Studio 4 min to Universal

Private 2BR Guesthouse + Pool-Heart of Kissimmee!

Thousand Oaks Peaceful Studio with Private Pool

The Little House

~Elegant Suite • Luxe Pool • Prime Orlando Stay
Guesthouse rentals with a washer and dryer

Cozy Lake View Stay

Relaxing Private Studio in the Trees!

The 𝕆𝕣𝕝𝕒𝕟𝕕𝕠 is the first step in the process.

Beautiful room for couples

Boutique Suite in Orlando

Cozy Vacation Guesthouse Near Universal

Charming & Cozy Guest House Minutes from Disney

Beautiful garage suite w/washer and dryer
Quick stats about guesthouse rentals in Kissimmee
Total rentals
40 properties
Nightly prices starting at
$41 CAD before taxes and fees
Total number of reviews
1.7K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Destinations to explore
- Seminole Vacation rentals
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- Rentals with beach access Kissimmee
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- Rentals with an accessible height bed Kissimmee
- Rentals with a fireplace Kissimmee
- Rentals with breakfast Kissimmee
- Condo rentals Kissimmee
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- Hotel rentals Kissimmee
- Resort rentals Kissimmee
- Rentals with lake access Kissimmee
- Rentals with outdoor seating Kissimmee
- Pet-friendly rentals Kissimmee
- Family-friendly rentals Kissimmee
- Rentals with a kayak Kissimmee
- Rentals with a sauna Kissimmee
- Vacation home rentals Kissimmee
- Mansion rentals Kissimmee
- Rentals with an EV charger Kissimmee
- Private suite rentals Kissimmee
- Rentals with pools Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Cottage rentals Kissimmee
- Beachfront rentals Kissimmee
- Waterfront rentals Kissimmee
- Rentals with a washer and dryer Kissimmee
- Rentals with a hot tub Kissimmee
- Apartment rentals Kissimmee
- Rentals with a home theater Kissimmee
- Fitness-friendly rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Cabin rentals Kissimmee
- Rentals with an accessible height toilet Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Guesthouse rentals Florida
- Guesthouse rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- Old Town Kissimmee
- SeaWorld Orlando
- Discovery Cove
- Disney Springs
- Disney's Animal Kingdom Theme Park
- ESPN Wide World of Sports
- Magic Kingdom Park
- Epcot
- Amway Center
- Aquatica
- Island H2O Water Park
- Walt Disney World Resort Golf
- Disney's Hollywood Studios
- ChampionsGate Golf Club
- ICON Park
- Universal CityWalk
- Kissimmee Lakefront Park
- Southern Dunes Golf and Country Club
- Universal's Islands of Adventure
- Crayola Experience