
Guesthouse vacation rentals in Winter Haven
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Winter Haven
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 Winter Haven guesthouse rentals
Family-friendly guest house rentals

The Forrestry

Private Carriage Studio, Mins to Dwntwn, FSC

Private 2BR Guesthouse + Pool-Heart of Kissimmee!

Oasis in the city, New in the market

BeachGuyDave's Reunion Guesthome

Cottage in Dixieland

Blue Pool Cottage, fenced courtyard

Comfort and Privacy - MR2
Guest house rentals with a patio

Modern and cozy Studio in the heart of Orlando

Lakeside Palm Escape

King-size Studio 4 min to Universal

Little Blue House of Kissimmee w/ private entrance

Kissimmee Studio

Florida Paradise

Thousand Oaks Peaceful Studio with Private Pool

Cozy Casita close to downtown & Florida southern
Guest house rentals with a washer and dryer

Comfy Guest House

Cozy King Suite

Cottage in Lakeland w/ Parking

The Lake Hunter Hideout

Modern Comfort, Pet Friendly, 2 King Beds!

Modern Guest Studio (Private) Pool / Spa available

Cozy Winter Haven Guesthouse 1

Charming & Cozy Guest House Minutes from Disney
Quick stats about guesthouse rentals in Winter Haven
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
Total number of reviews
1.7K 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
Destinations to explore
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- Kid-friendly rentals Winter Haven
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Universal Orlando Resort
- Old Town Kissimmee
- Discovery Cove
- SeaWorld Orlando
- Disney's Animal Kingdom Theme Park
- Disney Springs
- Raymond James Stadium
- Busch Gardens Tampa Bay
- ESPN Wide World of Sports
- Amalie Arena
- Amway Center
- Magic Kingdom Park
- Epcot
- Aquatica
- Walt Disney World Resort Golf
- Reunion West
- Island H2O Water Park
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Kissimmee Lakefront Park
- ICON Park