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Vacation Rentals & Villas in Winter Garden

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7,606 villas

' Special' 5 Star Vacation Home Near Attractions

Winter Garden house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 48 minutes

Price per night from

$223

Only Minutes to Disney World - Fully Furnished

Winter Garden villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$161

Beautiful Vacation Home 4 Miles from Disney

Winter Garden house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$143

Great rentals within 20 miles that match your search

417LaMirage at Regal Palms Resort & Spa-Pet Friendly & All Resorts fees included

Orlando townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 29 minutes

Price per night from

$183

KYLEMORE

Davenport villa

5 bedrooms / 3 bathrooms / sleeps 11

Price per night from

$183

Enchanting Star Lake View House Pool, and Jacuzzi

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 10

“Great vacation house” The house was very comfortable and everything was clean. My 7 year old son enjoyed the pool very much. It was a last minute reservation and everything was very smooth and easy. I will definitely recommend this to my friends. Thanks!

Responds fast! avg. 2 hours 57 minutes

Price per night from

$202

Savannah

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

“Excellent as usually” We just got back again and the house was excellent as usually no complaints at all y'all will definitely enjoy it.

Responds fast! avg. 3 hours 36 minutes

Price per night from

$100

Jasmine Villa

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 9 minutes

Price per night from

$201

Marcellas Luxury Private Gated Villa

Kissimmee villa

5 bedrooms / 7 bathrooms / sleeps 12

Price per night from

$199

Palm View

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

“Very nice unit.” Would give it a 8 out of 10 review. A few minor thing would make it nicer. Fix rollers on patio doors. Latch sets do not lock on some bedroom and bathroom doors. Garage door is very heavy, and doesn't lock easily, power operator would be nice. Light over kitchen table needs a higher out put bulb.

Responds fast! avg. 2 hours 12 minutes

Price per night from

$132

Beautiful 3 Bedroom Home with WIFI conveniently located near Disney

Kissimmee townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$166

Southern Serenity

Orange Tree villa

5 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 53 minutes

Price per night from

$218

Charming Townhouse with Pool and Tennis Court in Gated Community

Kissimmee townhouse

3 bedrooms / 2 bathrooms / sleeps 6

“Great location” This was the perfect location to get to and from all Disney attractions with zero traffic. So quick and easy! Carpet and couches could use some updating but overall - great value and very happy with our stay!

Price per night from

$100

Mickeys Clubhouse Windsor Palm Frozen & New Minion themed rooms

Kissimmee house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 57 minutes

Price per night from

$202

Disney Villa Highgate Park

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 1 hour 31 minutes

Price per night from

$228

Orlando condo at Legacy Dunes - resort amenities

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$78

Florida Jewels

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$187

Fantastic Orange Blossom Villa includes a Gameroom and Private Pool

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

“excellent” great location, clean, quite.... great for a family get away. game room needs update, pool is big. nice time with the family.

Price per night from

$143

Villa Linton - Beautiful Florida Home with Themed Bedrooms

Kissimmee villa

5 bedrooms / 3 bathrooms / sleeps 10

“Large home with easy access to Disney” This home was large enough for our whole family (7 adults) to sleep comfortably and it was so easy to get to the parks quickly before the crowds! Our adult children felt like kids again in the Scooby Doo room. The kitchen was large enough to cook family meals, and grocery stores are very nearby. Our only "wishes" while we were there were to have an outdoor grill and to have a TV in the family room large/loud enough for all of us to hear (the room was comfortable, though). We liked the gated community, but the streets are very narrow and with lots of parked cars, if you're driving a large vehicle you have to be very careful. The owner was superbly kind and quick with communicating. We'd definitely stay here again.

Responds fast! avg. 1 hour 31 minutes

Price per night from

$156

Star Florida Villa in Orlando-10 mins to Disney

Davenport villa

4 bedrooms / 4 bathrooms / sleeps 12

“Pancalanine Post Thanksgiving Celebration Trip!!!” Thank you Natalie for your beautiful, cozy, and clean home!!! We had a sensational time from the second we checked in til the second we left...the kids all enjoyed the play room to its fullest and the pool & hot tub was a fantastic retreat after a long day at the parks! I would highly recommend this home to anyone looking to enjoy quality time in the Orlando area...way better value than those overpriced hotel resorts!!! Our experience was an (a++++++++)

Price per night from

$134

Orlando Villa USA - Indian Ridge - 3 miles to Disney

Kissimmee villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$171

Kingfisher Grove - luxury home from home near Disney

Clermont villa

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 45 minutes

Price per night from

$148

My-Villa-in-Florida

Davenport villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$166

Disney and Relaxation

Davenport townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$112

Calusa Villa is a 6 bedroom 4 bathroom detached Villa.

Davenport villa

6 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 1 hour 31 minutes

Price per night from

$342

Secret Key Cove Villa

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 41 minutes

Price per night from

$160

SKC VIlla

Kissimmee villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 41 minutes

Price per night from

$160

Orlando Holiday Homes Online

Davenport house

4 bedrooms / 3 bathrooms / sleeps 8

“Christmas/New Years at Disney” We LOVED our stay!! House was beautiful and had everything we needed. Thank you for helping us make this Christmas/New Years a memory our kiddos and us as parents will remember for a lifetime!!

Responds fast! avg. 1 hour 28 minutes

Price per night from

$205

Responds fast! avg. 10 minutes

Price per night from

$314

Gorgeous Vacation Home with WiFi, on Yellow Lantana Ln

Kissimmee townhouse

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$159

Ibis Villa

Clermont villa

4 bedrooms / 3 bathrooms / sleeps 8

“"Great vacation home"” This Florida vacation home is very beautiful and spacious. It is well equipped with dishes, cookware, towels and movies. There are even pool towels and sport equipment available. Our family really enjoyed the pool, spa and the play room. It is located in a quiet neighborhood with nearby restaurants and attractions. We are definitely looking forward to staying there again.

Responds fast! avg. 3 hours 29 minutes

Price per night from

$139

Lovely Mango Keys Home includes WiFi and Hot Tub

Kissimmee house

2 bedrooms / 2 bathrooms / sleeps 5

“Very nice, clean, quite” Was very nice and clean. Maybe the only thing should be te a/c in masterroom wasn't cold. Everything else was very good and enjoyable.

Responds fast! avg. 58 minutes

Price per night from

$86

Responds fast! avg. 3 hours 36 minutes

Price per night from

$200

Sanitized, Private Pool, Large Yard for Kids, Wifi, BBQ, Gated Resort Amenities

Orlando villa

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 36 minutes

Price per night from

$126

Emerald Villas

Davenport villa

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$171

2 room Celebration Disney Poolside SPA-Golf

Celebration condo

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$225

Golf Resort Private Pool Golf Tennis SPA Villa

Davenport house

12 bedrooms / 6 bathrooms / sleeps 21

Price per night from

$878

High Grove Villa

Clermont villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$149

Viewing 38 of 7,606
rentals in Winter Garden

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