Pet-friendly vacation rentals in Winter Garden

Unique Spacious Home w/ Pool near Downtown Orlando

Nestled on a quiet street, 15 mins from Downtown Orlando. This home has a massive pool, hot tub, water fountain, real outdoor and indoor fire place, outdoor patio area w/seating. The Kitchen is equipped with everything you need to make delicious meals, and there are two living areas to provide ample space for relaxation. There is also a designated office area to take work calls. ☀ College Park – 10 mins ☀ Downtown Orlando – 15 mins ☀ Universal Studios – 28 mins ☀ Walt Disney World – 34 mins

The Perfect Home - Heated Pool - Next to Universal

This luxurious, modern, completely remodeled single-family home with HEATED pool and spacious FULLY FENCED backyard in one of Orlando's best neighborhood! Centrally located from all Orlando has to offer: ☆ 1.7 miles from Universal Studios ☆ 2.6 miles to Restaurant Row ☆ 4.5 miles to Orange County Convention Center ☆ 6.5 miles to Seaworld ☆ 10 miles to Disney World This home offers upscale living space with stunning outdoor area to kick back and enjoy after a long day at the parks.

The Swift House

Steps from Plant St. This private cute cottage with Modern amenities is a Swiftie Oasis. Even if you aren’t a fan- you will love the designated off street covered parking, Fenced in .25 acre back yard, delicious restaurants, coffee shops, French bistro, brewery, wine bar, rooftop lounges, shops, the W Orange trail, top farmers market, festivals and more. Walk to the lake! Very Safe. 20 mins to Disney. Enjoy the charm of Historic Downtown WG or stay in and indulge in all things Taylor $wift.

1921 Bungalow in Historic Downtown Winter Garden

Step into timeless charm with this beautifully restored 2-bed, 1-bath historic 1920s home located in downtown Winter Garden. This bungalow sleeps 6 w/two beds & a sleeper sofa. Enjoy morning coffee in the sunroom, a large yard and firepit. Dogs are welcome. A block away from Plant Street that offers boutique shopping, local restaurants, a Splash Pad, the Farmer's Market, and community events. Bike on the West Orange Trail or visit Lake Apopka and Newton Park. Only 12 miles to Disney/parks.

Lake Front Home with private Dock on Lake Louisa

Beautiful lake front home on Lake Louisa. The home sits under towering Cypress trees and is 15 feet from the waters edge. Enjoy breathtaking views of Lake Louisa in the very large great room. Enjoy a game of pool on the pool table, watch cable tv, or walk out onto our private shaded dock where you can fish, swim, enjoy the views, read, play a game of Bimini ring toss, or just relax and unwind. For the safety our guests we allow 2 days between to allow cleaning and disinfecting of the house

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.

Spacious Getaway ~ Heated LED Pool & Ping Pong

Welcome to your Spacious Getaway! Exterior Features: ★ LED Lights in Pool and on Pool Cage ★ Fenced-in yard & Fire-pit ★ Doorbell & Driveway Camera for safety Interior Features: ★ Ping Pong Table ★Large Shower in Master Bathroom ★ROKU on each TV Extras: ★ Heated Pool up to 95 Degrees - $50 per day (Pool Water is normally at 75 degrees without the Pool Heater) ⚠️ Pet-Friendly, but the pet must be added to the reservation ($75 Pet fee)⚠️ {Willing to Negotiate Monthly Prices}

Charming Downtown Apartment - Walk to Everything

Stay in the heart of historic downtown Clermont- steps from the lakefront, breweries, shops, & dining. This light-filled, stylish apartment above our garage offers cozy aesthetics, comfy beds, a double shower, two spacious bedrooms, and a smart TV. Thoughtfully stocked for a stress-free stay, with garage storage for your bikes or paddle gear upon request. More than a stay—we proudly offer a distinct Clermont experience. We hope you love our charming town just as much as we do!

The silver cottage

This unique place has a style all its own. Dogs Welcome! ( Pet fee applies). Newly renovated featuring white tiles throughout, granite countertops, fully equipped kitchen, smart tv in all bedrooms and living space. Modern stylish garden bath with floating cabinetry. This unit also features work space with desk and chair. One car garage and extra parking space included at no extra charge. At this time we are only accepting one pet per reservation, max 30lbs.

Stay A While

Welcome to Your Secluded Getaway Enjoy a quiet retreat minutes from supermarkets and Florida’s top attractions. Top Attractions Island H2O: 23m | Epcot: 27m | SeaWorld: 32m Disney Springs: 34m | Universal: 36m Legoland: 1h | Busch Gardens: 1h 27m Shopping & Dining Winter Garden/Clermont: 14m Outlets: 28m | Florida Mall: 35m | I-Drive: 40m Travel MCO Airport: 40m Oversized Parking: Dedicated space for boats, RVs, and moving trucks. storage only

Modern Suite in the Heart of Downtown Clermont 101

Experience luxury and excitement in our chic modern suite nestled in the vibrant heart of downtown Clermont. Perfectly poised for Triathletes, this suite is a beacon of comfort and convenience, mere steps away from charming downtown boutiques, delightful restaurants and local breweries. The location is unparalleled with close proximity to the celebrated Clermont/Minneola Trail, esteemed host of prestigious Triathlons and the serene Waterfront Park.

Private Country House | 16 Guests | Gatherings

Bring the whole family to this private 5-acre retreat, situated in one of the few hilly regions of Florida. Enjoy privacy, nature, spectacular sunsets, and starry nights—perfect for relaxing or enjoying outdoor activities. ⚠️ Gatherings require prior approval—please contact us before booking. Note: There is another house on the property that may be rented by other guests. Both are completely private, with no shared areas or parking.