Title: Book the Best Kissimmee WINERY Hotels in 2026 | Expedia.ca

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![Moment Open](https://images.trvl-media.com/place/7927/b63b8a82-d8e7-4936-9033-5b5daf0dfa65.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Winery Hotels in Kissimmee, FL from CA $92

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## Check availability on Kissimmee Winery Hotels

Tonight

[Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=7927&startDate=2025-12-18&endDate=2025-12-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=7927&startDate=2025-12-19&endDate=2025-12-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7927&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=7927&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Kissimmee hotels with winery

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/f9ab812e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/fe23c7c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/6866cf08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109920000/109917500/109917441/cf74ec85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Disney Universal Family Villa Resort with Elevator, Pool and many amenities!

[](https://www.expedia.ca/Orlando-Hotels-Disney-Universal-Family-Villa-Resort-With-Elevator.h109917441.Hotel-Information)

Kissimmee

CA $135

CA $317 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Orlando-Hotels-Disney-Universal-Family-Villa-Resort-With-Elevator.h109917441.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/124000000/123110000/123108900/123108895/44bde464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/124000000/123110000/123108900/123108895/ac81ee6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/124000000/123110000/123108900/123108895/1919d41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123110000/123108900/123108895/5d2d8c4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Resort-Style 4BR Home Close to Parks and Pool

[](https://www.expedia.ca/Orlando-Hotels-Resort-Style-4BR-Home-Close-To-Parks-And-Pool.h123108895.Hotel-Information)

Kissimmee

CA $143

CA $530 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Orlando-Hotels-Resort-Style-4BR-Home-Close-To-Parks-And-Pool.h123108895.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22000/21968/8876466a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/22000/21968/c99ccb46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22000/21968/0c26b09c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Poolside bar](https://images.trvl-media.com/lodging/1000000/30000/22000/21968/6baee961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maingate Lakeside Resort

[](https://www.expedia.ca/Orlando-Hotels-Maingate-Lakeside-Resort.h21968.Hotel-Information)

Kissimmee

4.4/10

(2500)

"Staff was very helpful"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Victor

CA $48

CA $92 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Orlando-Hotels-Maingate-Lakeside-Resort.h21968.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/122000000/121740000/121733800/121733762/9cfc6887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/122000000/121740000/121733800/121733762/ddba817c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/122000000/121740000/121733800/121733762/5ebb4f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121740000/121733800/121733762/5b8063c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Peaceful 3BR Family Condo ✧ Minutes to Disney – Caribe Cove Resort!

[](https://www.expedia.ca/Orlando-Hotels-Peaceful-3BR-Family-Condo-Minutes-To-Disney-Caribe-Cove-Resort.h121733762.Hotel-Information)

Kissimmee

CA $88

CA $535 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Orlando-Hotels-Peaceful-3BR-Family-Condo-Minutes-To-Disney-Caribe-Cove-Resort.h121733762.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/101000000/100780000/100778400/100778392/4724e670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/101000000/100780000/100778400/100778392/af90a0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100780000/100778400/100778392/d65181c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100780000/100778400/100778392/ca5566f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SPACIOUS 1 BEDROOM LOFT IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2769

[](https://www.expedia.ca/Orlando-Hotels-1-BEDROOM-WITH-LOFT-DISNEY-AREA-VACATION-RENTAL-AWARD-WINNING-MILL-CREEK-RESORT.h100778392.Hotel-Information)

Kissimmee

10/10

Exceptional

(15)

"We extremely enjoyed our stay! Nice, quite, and perfect for our small family"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

David

CA $123

CA $309 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Orlando-Hotels-1-BEDROOM-WITH-LOFT-DISNEY-AREA-VACATION-RENTAL-AWARD-WINNING-MILL-CREEK-RESORT.h100778392.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/101000000/100470000/100463800/100463789/9f065b1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100470000/100463800/100463789/3cdad547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100470000/100463800/100463789/b6e53e30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100470000/100463800/100463789/428a2712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SPACIOUS 2 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2763

[](https://www.expedia.ca/Orlando-Hotels-2-BEDROOM-DISNEY-AREA-VACATION-RENTAL-IN-AWARD-WINNING-MILL-CREEK-RESORT.h100463789.Hotel-Information)

Kissimmee

9.6/10

Exceptional

(8)

"Great location, very good property! Cleaning the floors could use a bit more attention to detail but overall we had a nice stay."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mark S.

[](https://www.expedia.ca/Orlando-Hotels-2-BEDROOM-DISNEY-AREA-VACATION-RENTAL-IN-AWARD-WINNING-MILL-CREEK-RESORT.h100463789.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/101000000/100890000/100880500/100880482/c1c5a336.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100890000/100880500/100880482/9dabe4f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/101000000/100890000/100880500/100880482/c45a063b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100890000/100880500/100880482/78f5bdf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SPACIOUS 1 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 1377

[](https://www.expedia.ca/Orlando-Hotels-1-BEDROOM-DISNEY-AREA-VACATION-RENTAL-IN-AWARD-WINNING-MILL-CREEK-RESORT.h100880482.Hotel-Information)

Kissimmee

CA $98

CA $278 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Orlando-Hotels-1-BEDROOM-DISNEY-AREA-VACATION-RENTAL-IN-AWARD-WINNING-MILL-CREEK-RESORT.h100880482.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/124000000/123090000/123081000/123080988/19c124c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball](https://images.trvl-media.com/lodging/124000000/123090000/123081000/123080988/4e97ff43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/124000000/123090000/123081000/123080988/4e0d283a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, foosball](https://images.trvl-media.com/lodging/124000000/123090000/123081000/123080988/b27ebded.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family 5BR w/ Pool & Grill Near Disney Magic

[](https://www.expedia.ca/Orlando-Hotels-Family-5BR-W-Pool-Grill-Near-Disney-Magic.h123080988.Hotel-Information)

Kissimmee

CA $172

CA $810 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Orlando-Hotels-Family-5BR-W-Pool-Grill-Near-Disney-Magic.h123080988.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100460000/100454400/100454338/9def6712.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/101000000/100460000/100454400/100454338/d691a9fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100460000/100454400/100454338/c1693541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100460000/100454400/100454338/ea36bf5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SPACIOUS 1 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2774

[](https://www.expedia.ca/Orlando-Hotels-1-BEDROOM-VACATION-RESORT-RENTAL-IN-AWARD-WINNING-MILL-CREEK-RESORT.h100454338.Hotel-Information)

Kissimmee

CA $123

CA $286 total

includes taxes & fees

Dec 31 - Jan 1, 2026

[](https://www.expedia.ca/Orlando-Hotels-1-BEDROOM-VACATION-RESORT-RENTAL-IN-AWARD-WINNING-MILL-CREEK-RESORT.h100454338.Hotel-Information)

![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/121000000/120710000/120709700/120709688/a343eb14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120710000/120709700/120709688/ebc9674f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/121000000/120710000/120709700/120709688/789f3adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/121000000/120710000/120709700/120709688/8e53c51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Family Home: Clubhouse, Themed Rooms & Backyard

[](https://www.expedia.ca/Orlando-Hotels-Family-Home-Clubhouse.h120709688.Hotel-Information)

Kissimmee

CA $110

CA $641 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Orlando-Hotels-Family-Home-Clubhouse.h120709688.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-01&endDate=2026-01-02&regionId=7927&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

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