
Guesthouse vacation rentals in Winter Haven
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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

Tiny Lakeview Suite Near Disney & Universal

Cozy Lake View Stay

Cozy Casita close to downtown & Florida southern

Modern Comfort, Pet Friendly, 2 King Beds!

Blue Pool Cottage, fenced courtyard

Cozy Tiny house in Kissimmee close the parks

Cozy Guesthouse 60% Off Monthly Rate Inc Utilities

Charming Guesthouse A
Guest house rentals with a patio

The Forrestry

Inviting 3 br haven: vaca/work

Kissimmee Studio

Florida Paradise

Thousand Oaks Peaceful Studio with Private Pool

Beautiful room for couples

Cottage in Dixieland

Charming Dixieland Casita
Guest house rentals with a washer and dryer

Cozy Legoland Guest House with Pool

Comfy Guest House

Cozy Oaks Suite

Private Carriage Studio, Mins to Dwntwn, FSC

Cozy Guesthouse in Winter Haven 2

The Lake Hunter Hideout

Charming & Cozy Guest House Minutes from Disney

Cozy guest house w/ fenced yard and hot tub
Quick stats about guesthouse rentals in Winter Haven
Total rentals
20 properties
Nightly prices starting at
R522 ZAR 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
- Seminole Vacation rentals
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- Cottage rentals Winter Haven
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- Waterfront rentals Winter Haven
- Rentals with a fire pit Winter Haven
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- Family-friendly rentals Winter Haven
- Rentals with a patio Winter Haven
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- Guesthouse rentals Florida
- Guesthouse rentals United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Old Town Kissimmee
- Discovery Cove
- Disney Springs
- Disney's Animal Kingdom Theme Park
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- ESPN Wide World of Sports
- Epcot
- Amway Center
- Aquatica
- Walt Disney World Resort Golf
- Island H2O Water Park
- Amalie Arena
- Disney's Hollywood Studios
- Streamsong Resort
- Universal CityWalk
- ChampionsGate Golf Club
- ICON Park