
Guest house holiday rentals in Winter Park
Find and book unique guest house rentals on Airbnb
Top-rated guest house rentals in Winter Park
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for guest house rentals in Winter Park
Family-friendly guest house rentals

Sapphire Cottage - sleeps 6, on 5 acres with canal

Private Luxurious Apt. - Historic Downtown Orlando

Black House- Private Cottage in Thornton Park!

Historic lakefront guesthouse

Guest Home | MCO & Downtown 15 Min | Private Unit

Vintage Florida Vibes House

Adorable Studio Guest House

Private full kitchen near Disney & Epic Universe!
Guest house rentals with a patio

King-size Studio 4 min to Universal

Little Blue House of Kissimmee w/ private entrance

Livingston Hideaway - 2 Blocks From Lake Eola

Enjoy downtown: modern studio w/ kitchenette

The Little House

Modern & Cozy Retreat - Orlando City Center Epic

Adorable Private 1-Bedroom guesthouse with deck

Cozy Vacation Guesthouse Near Universal
Guest house rentals with a washing machine and dryer

Your Home Away From Home

Relaxing Private Studio in the Trees!

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

Modern Guest Studio (Private) Pool / Spa available

1926 Spanish Carriage House Lower

tinyhouse on the edge of orlando + winter park

Palmetto Pool Retreat

20 | Excellent | Above Average
Quick stats about guest house rentals in Winter Park
Total rentals
20 properties
Total number of reviews
2.5K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Local attractions
Orlando Science Center, Harry P. Leu Gardens and Orlando Museum of Art
Destinations to explore
- Seminole Holiday rentals
- Miami Holiday rentals
- Central Florida Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
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- Kissimmee Holiday rentals
- Four Corners Holiday rentals
- Panama City Beach Holiday rentals
- Rentals with a patio Winter Park
- Family-friendly rentals Winter Park
- Rentals with outdoor seating Winter Park
- Rentals with a washing machine and dryer Winter Park
- Fitness-friendly rentals Winter Park
- Rentals with a hot tub Winter Park
- Private suite rentals Winter Park
- Pet-friendly rentals Winter Park
- Rentals with pools Winter Park
- Apartment rentals Winter Park
- Flat rentals Winter Park
- Rentals with an EV charger Winter Park
- Waterfront rentals Winter Park
- House rentals Winter Park
- Rentals with lake access Winter Park
- Rentals with a fireplace Winter Park
- Rentals with a firepit Winter Park
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- Reunion Resort Golf Courses - Palmer & Watson
- Reunion West
- Disney Springs
- Ventura Country Club
- Universal's Volcano Bay
- Harry Potter and the Escape from Gringotts™
- Disney's Animal Kingdom Theme Park
- Epcot
- Bob Makinson Aquatic Center
- Wekiwa Springs State Park
- New Smyrna Beach Golf Course
- Bok Tower Gardens
- Lake Kissimmee State Park
- Willowbrook Golf Course
- Southern Dunes Golf and Country Club
- Arlington Ridge Golf Club
- Mount Dora Golf Club
- Lake Louisa State Park
- Island H2O Water Park
- ChampionsGate Golf Club
- Kings Ridge Golf Club
- Clerbrook Golf & RV Resort
- Mystic Dunes Golf Club
- Falcon's Fire Golf Course
- Things to do Winter Park
- Things to do Orange County
- Art and culture Orange County
- Sports activities Orange County
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- Nature and outdoors Florida
- Wellness Florida
- Food and drink Florida
- Art and culture Florida
- Sports activities Florida
- Things to do United States
- Tours United States
- Wellness United States
- Art and culture United States
- Nature and outdoors United States
- Sports activities United States
- Sightseeing United States
- Entertainment United States
- Food and drink United States