
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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Kissimmee guesthouse rentals
Family-friendly guest house rentals

Private Pool Studio Close to Rest & Attractions

Relaxing Private Studio in the Trees!

A place with a view

BeachGuyDave's Reunion Guesthome

Paradise nook near Orlando's theme parks

Modern & Cozy Studio|Private Retreat w Kitchenette

The Cottage A Pet Friendly Guesthouse

BRAND NEW! 1 Bedroom APT
Guest house rentals with a patio

Modern and cozy Studio in the heart of Orlando

Private 2BR Guesthouse + Pool-Heart of Kissimmee!

Cozy new guesthouse to yourself.

Cozy Corner near Orlando Airport

Thousand Oaks Peaceful Studio with Private Pool

The Little House

Elegant and cozy guest house

Convenient Getaway Near Orlando Hotspots
Guest house rentals with a washer and dryer

Cozy Guesthouse w/ King Bed - Near Top Attractions

Lakeside Palm Escape

Cozy Lake View Stay

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

Boutique Suites in Orlando

Modern Guest Studio (Private) Pool / Spa available

1/1 Private Guesthouse in Orlando (South Downtown)

Charming & Cozy Guest House Minutes from Disney
Quick stats about guesthouse rentals in Kissimmee
Total rentals
40 properties
Nightly prices starting at
R531 ZAR 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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- Mansion rentals Kissimmee
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- Rentals with an accessible height bed Kissimmee
- Rentals with a fireplace Kissimmee
- Rentals with a hot tub Kissimmee
- Serviced apartment rentals Kissimmee
- Resort rentals Kissimmee
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- Rentals with a fire pit Kissimmee
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- Fitness-friendly rentals Kissimmee
- Beachfront rentals Kissimmee
- Rentals with a sauna Kissimmee
- House rentals Kissimmee
- Lakehouse rentals Kissimmee
- Family-friendly rentals Kissimmee
- Apartment rentals Kissimmee
- Rentals with beach access Kissimmee
- Rentals with breakfast Kissimmee
- Private suite rentals Kissimmee
- Rentals with a washer and dryer Kissimmee
- Rentals with lake access Kissimmee
- Rentals with an accessible height toilet Kissimmee
- Rentals with pools Kissimmee
- Hotel rentals Kissimmee
- Rentals with outdoor seating Kissimmee
- Cabin rentals Kissimmee
- Villa rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with a kayak Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Rentals with a home theater Kissimmee
- Waterfront rentals Kissimmee
- Tiny house rentals Kissimmee
- Cottage 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
- Disney's Hollywood Studios
- ChampionsGate Golf Club
- ICON Park
- Walt Disney World Resort Golf
- Universal CityWalk
- Kissimmee Lakefront Park
- Southern Dunes Golf and Country Club
- Crayola Experience
- Universal's Islands of Adventure