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House vacation rentals in Winter Garden

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Top-rated house rentals in Winter Garden

Guests agree: these houses are highly rated for location, cleanliness, and more.

Guest favorite
Home in Clermont
Stylish Villa Private Pool-SPA Near Parks Disney!
Stylish villa 4 bed/3 bath family home with private facing pool & SPA, living room, family room, kitchen, breakfast bar, dining table, a game room, Wi-Fi, smart TVs, wheelchair accessible, close to the parks, shops, and restaurants, Pool & SPA heater at additional cost, located at Glenbrook community. WELL.... we have it all and much more to enjoy so read on!! Pool & SPA heater fee is 25 dollars per day. BBQ grill is an additional 40 dollars (for the whole stay, which includes gas and cleaning).
$125 per night
Guest favorite
Home in Minneola
Spacious Home ~ Heated LED Pool & Ping Pong
Welcome to your Spacious Getaway! With over 70 amenities offered, our goal is to provide an unforgettable experience for our guests! Exterior Features: ★ Heated Pool up to 95 Degrees - ($25 a Day to Heat the Pool) ★ LED Lights on pool cage ★ Fenced-in yard & Fire-pit ★ Doorbell & Driveway Camera for safety Interior Features: ★ White/Clean Linens ★ TV with Netflix ★ Ping Pong Table ★ Shower Panel in Guest Bathroom ★Large Shower in Master Bathroom {Willing to Negotiate Monthly Prices}
$200 per night
Guest favorite
Home in Winter Garden
Cozy Winter Garden Home 20 MINUTES FROM DISNEY
Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.
$99 per night

Popular amenities for Winter Garden house rentals

House rentals with a pool

Guest favorite
Home in Orlando
Perfect location near Disney and Universal
$78 per night
Superhost
Home in Clermont
ABM Villa Private Pool-SPA Near all Parks Disney!
$125 per night
Guest favorite
Home in Clermont
Vacation Villa Minutes From Disney Theme Parks
$151 per night
Superhost
Home in Clermont
Relaxing Family Villa w/ Pool! Close to Disney!
$139 per night
Guest favorite
Home in Kissimmee
Disney Orlando vacation home with private pool 2
$170 per night
Guest favorite
Home in Clermont
Great House w/Heated Pool;Near all Parks!
$139 per night
Guest favorite
Home in Clermont
Caribe Villa Brisa- Disney is only 6 miles away!
$189 per night
Superhost
Home in Orlando
Modern, Clean Home, 5 min from Universal Studios
$167 per night
Guest favorite
Home in Kissimmee
Amazing Pool * Spacious 3BR House near Disney
$177 per night
Superhost
Home in Kissimmee
Tropical Villa,Private Pool, 3.5 miles from Disney
$183 per night
Guest favorite
Home in Kissimmee
Gorgeous Florida Getaway in Central Location!
$238 per night
Guest favorite
Home in Davenport
Disney Area Luxury Villa with Private Pool
$129 per night

Weekly house rentals

Guest favorite
Home in Clermont
Clermont Cottage Near the Lake
May 3 – 10
$104 per night
Guest favorite
Home in Clermont
Lake Front Home with private Dock on Lake Louisa
Nov 2 – 9
$149 per night
Guest favorite
Home in Apopka
Farm feel in the city
May 23 – 30
$98 per night
Guest favorite
Home in Orlando
Downtown Orlando-Harwood House-Lake Eola-Historic
Oct 19 – 26
$87 per night
Guest favorite
Home in Orlando
The Lake House - Next to Universal Studios - NEW ♥️
Apr 17 – 24
$274 per night
Guest favorite
Home in Orlando
10 Minutes to Universal - Charming Private Home
May 9 – 16
$102 per night
Guest favorite
Home in Kissimmee
Windsor Orlando Private Arcades,Theater,Pool-Spa
Sep 30 – Oct 7
$445 per night
Guest favorite
Home in Orlando
The Comfy Milk District Home | Downtown |
Apr 17 – 24
$77 per night
Guest favorite
Home in Clermont
Our Poolhome by the Mouse house with Game Room.
Nov 6 – 13
$145 per night
Guest favorite
Home in Kissimmee
"Vista Lago"Hotel Amenities/lake view,private pool
Jul 4 – 11
$383 per night
Superhost
Home in Davenport
Orlando Disney area home
May 10 – 17
$95 per night
Guest favorite
Home in Four Corners
Style & Luxury: Pool, Spa, Views, Cinema & Games
Oct 23 – 30
$405 per night

Private house rentals

Guest favorite
Home in Orlando
LUXURY 𝕄𝕠𝕕𝕖𝕣𝕟 𝔽𝕒𝕣𝕞𝕙𝕠𝕦𝕤𝕖 𝙲𝚁𝚎𝚊𝚃𝚒𝚅𝚎 𝙷𝚞𝙱 near DOWNTOWN
$114 per night
Guest favorite
Home in Orlando
Hidden Gem in SODO! - MCO ~16min
$89 per night
Guest favorite
Home in Orlando
Walk Everywhere DTO Thornton Park | Free Parking
$126 per night
Guest favorite
Home in Orlando
Stylish New 1 Bed + Office ☼ In Downtown Orlando
$125 per night
Guest favorite
Home in Winter Garden
Cozy home in Winter Garden
$126 per night
Guest favorite
Home in Winter Garden
Winter Garden Experience
$136 per night
Guest favorite
Home in Winter Garden
Luxury Home Winter Garden Near Disney & Universals
$180 per night
Guest favorite
Home in Winter Garden
Pet Friendly Winter Garden Get-Away near Orlando
$65 per night
Guest favorite
Home in Ocoee
Completely Private and Cozy Studio
$59 per night
Superhost
Home in Winter Park
ꜱʟᴇᴇᴘꜱ 4, ᴡɪɴᴛᴇʀ ᴘᴀʀᴋ & ᴅᴏᴡɴᴛᴏᴡɴ
$102 per night
Guest favorite
Home in Clermont
ModernDisneyHome
$120 per night
Guest favorite
Home in Winter Garden
WATERFRONTWinterGdnHSE+VIEWS+Dock+Wildlife+Firepit
$438 per night

Quick stats about house rentals in Winter Garden

Total rentals

70 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

2.4K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Orange County
  5. Winter Garden
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