House vacation rentals in Winter Garden

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Top-rated house rentals in Winter Garden

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Guest favorite

Home in Montverde

4.97 out of 5 average rating, 106 reviews

The Legacy House - your home away from home.

Just a block away from the South Lake Bike Trail System, 18 minutes from beautiful Lake Minneola, and a mere 20 miles from the Disney Parks, and 5 minutes from the Bella Collina wedding venue, this peaceful neighborhood home will be a perfect spot to rest after a full day of fun. This is an ideal spot if you're coming for cycling events, fishing competitions, a wedding or simply to enjoy the most beautiful part of Florida! We hope you chose to book with us; it would be our pleasure to host you!

Jul 29 – Aug 5

G$32,530 GYD per night

Guest favorite

Home in Orlando

4.94 out of 5 average rating, 127 reviews

10 Minutes to Universal - Charming Private Home

Beautiful newly remodeled home centrally located. 3 bedrooms (2 King 1 Queen) and 2 full baths (1 walk in shower w/ grab bars). Carport. Huge and private yard to enjoy! Comfortable living room with big screen TV, couches and lazyboy recliners. Kitchen is fully stocked for cooking. Office desk and chair. Washer and Dryer. 10 Minutes to Universal Studios and just minutes more to International Drive, Mall of Millenia, Florida Mall, or Disney. Grocery, liquor, pizza, chinese within a 5 minute walk.

Oct 15 – 22

G$27,183 GYD per night

Guest favorite

Home in Orlando

4.94 out of 5 average rating, 374 reviews

Pet Welcome/Fully Fenced Backyard/Washer & Dryer

*IF YOU ARE BRINGING PET, please read house rules before a reservation. *Full House located walking distance to Camping World Stadium/3 miles to Dwtn & Amway Center/16 miles to Disney/6 miles to Universal Studios & Sea World/14 miles to MCO airport. *Bedroom #1: Queen mattress & Twin Trundle,TV. *Bedroom #2: Queen mattress. *Parking for 2 cars/Washer & Dryer. *Kitchen with amenities and stainless appliances. *Backyard fenced & Gazebo for families with kids. **Tenant living in attached studio**

Nov 30 – Dec 7

G$26,659 GYD per night

Guest favorite

Home in Minneola

4.98 out of 5 average rating, 111 reviews

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}

Jan 12 – 19

G$47,602 GYD per night

Guest favorite

Home in Orlando

4.95 out of 5 average rating, 313 reviews

*HALF HOME* (read desc) Pool/Disney/Universal

We LOVE hosting! Think of us as friends you’re staying with, but haven’t met yet. We are happy to interact, but also happy to remain out of sight to ensure your privacy. We live in the master (on OTHER SIDE w/own bath) when not traveling and we DO use kitchen. Everything else is exclusive to you! You get plenty of space & PRIVACY. Photos represent YOUR space (we use kitchen too, but rest is exclusive) If you’re not comfortable with on-site host w/kitchen usage, we aren’t right choice.

Jun 16 – 23

G$22,822 GYD per night

Guest favorite

Home in Winter Garden

4.92 out of 5 average rating, 167 reviews

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.

Jul 20 – 27

G$24,366 GYD per night

Guest favorite

Home in Clermont

4.99 out of 5 average rating, 157 reviews

Clermont Cottage Near the Lake

Enjoy your stay in beautiful sunny FL in our fully renovated 2 bed/2 bath home. We've added ENHANCED CLEANING AND DISINFECTING after every guest's stay. This home is located in a quiet neighborhood less than a mile from Clermont's WATERFRONT PARK and the WEST ORANGE TRAIL. It's a great location for Triathlons and activities at Victory Point. If you are visiting to enjoy Universal Studios and Disney, they are only 28 miles away! Come stay at our home with everything you'll need!

Sep 27 – Oct 4

G$25,102 GYD per night

Guest favorite

Home in Clermont

4.93 out of 5 average rating, 187 reviews

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 full disinfecting of the house.

Apr 16 – 23

G$35,829 GYD per night

Guest favorite

Home in Maitland

4.97 out of 5 average rating, 116 reviews

The Butterfly Bungalow near Park Ave

This 1950s bungalow has been lovingly restored to maintain it's Florida charm and offer simple comforts. Located in a family-friendly neighborhood just a few blocks from the Enzian Theater, the bungalow is close to restaurants and shops lining the cobblestone streets of Park Ave, and centrally located to historic areas of both Winter Park and Maitland. Park Ave shopping district - 1.5 miles Whole Foods - 0.8 miles Publix - 0.8 miles SunRail - 1.7 miles Downtown Orlando - 8 miles

Oct 7 – 14

G$27,967 GYD per night

Guest favorite

Home in Orlando

4.93 out of 5 average rating, 120 reviews

Hidden Gem in SODO! - MCO ~16min

Enjoy your stay in this cozy & comfy 1 bedroom and bath house located in the desirable South Downtown Orlando. Rest well in the large queen size bed, with a 65 inch smart TV, equipped with Netflix. Restaurants and stores in walking distance. Wifi & parking are included MCO Airport: ~16 Min Drive Disney: ~20 Min Drive Universal Studios: ~15 Min Drive Hollywood Studios: ~20 Min Drive Sea World: ~15 Min Drive Downtown Orlando: ~5 Min Drive

Apr 1 – 8

G$20,172 GYD per night

Guest favorite

Home in Ocoee

4.9 out of 5 average rating, 122 reviews

Lakeview Sunsets with Loft Escape West of Orlando

We are proud to announce No Smoking on premises property. This Duplex A Lake house overlooks Starke Lake in Central Florida. Great fishing, magnificent sunsets and Disney fireworks every night . Close to Disney 19 miles & 12 miles to Universal & 14 miles to Downtown Orlando. Other activities include air boating, Cape Cape Canaveral and centrally located just 1 hour from ocean or gulf. Please NO SMOKING on premises.

Aug 3 – 10

G$30,334 GYD per night

Guest favorite

Home in Orlando

4.9 out of 5 average rating, 178 reviews

Downtown Orlando-Harwood House-Lake Eola-Historic

You found a hidden gem within the heart of Downtown Orlando! Our completely renovated guesthouse sits amidst the quiet, tree-lined streets of Eola Heights Historic District, three blocks to beautiful Lake Eola. Enjoy nearby dining, shopping, and entertainment. Business travelers are minutes from Orange County Courthouse and Central Business District.

Feb 6 – 13

G$22,412 GYD per night