A pathway through a park with Spanish moss hanging from trees and a body of water in the background.

Winery Hotels & Resorts in Kissimmee from NZ$176

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Kissimmee Winery Hotels

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for Kissimmee hotels with winery

A modern living room with a glass dining table, leather sofas, and a flat-screen TV.
A park with a walking path, benches, and a gazebo.
A reception desk at Grand Lake and Lifetime of Vacations Resorts with a sign, a computer, and a security camera.
A tennis court with a surrounding fence, a palm tree, and a body of water in the background.

1. Grand Lake Resort

Grand Lake Resort
Kissimmee
United States
Leslie
NZ$176
includes taxes & fees
8 Nov - 9 Nov
Grand Lake Resort
An aerial view of a swimming pool with a heart-shaped design, surrounded by lounge chairs and umbrellas.
A modern living room with a grey sofa, a white bench, and a colorful rug. There is a kitchen area with a dining table and chairs, and a TV displaying a show.
A hotel room with two beds, red bedding, Mickey Mouse wall art, and a nightstand with a lamp.
A modern living room with a sofa, a coffee table, a TV, and a red Mickey Mouse painting on the wall.

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

Disney Universal Family Villa Resort with Elevator, Pool and many amenities!
Kissimmee
NZ$425
includes taxes & fees
31 Oct - 1 Nov
Disney Universal Family Villa Resort with Elevator, Pool and many amenities!
A modern kitchen with a white countertop, stainless steel sink, and wooden cabinets.
A bedroom with a bed, a dresser, a painting, and a door leading to another room.
A water park with multiple slides and a pool area.
A living room with a flat-screen TV, a glass coffee table, and a sofa.

3. Disney Magic in Windsor Hills Resort

Disney Magic in Windsor Hills Resort
Windsor Hills
NZ$550
includes taxes & fees
22 Nov - 23 Nov
Disney Magic in Windsor Hills Resort
A modern living room with a glass coffee table, a flat-screen TV mounted on a wooden shelf, and a decorative plant.
A modern living room with a flat-screen TV, a sofa, a coffee table, and a ceiling fan.
A large swimming pool with multiple lanes, surrounded by lounge chairs and umbrellas, and a playground area with slides and swings.
A residential complex with a central swimming pool, multiple tennis courts, and a parking area.

4. Disney Paradise: 2BR Villa, Near Magic & More! - 2306 SP

Disney Paradise: 2BR Villa, Near Magic & More! - 2306 SP
Kissimmee
NZ$746
includes taxes & fees
19 Nov - 20 Nov
Disney Paradise: 2BR Villa, Near Magic & More! - 2306 SP
Pool
A modern kitchen with white cabinets, a black refrigerator, a microwave, and a large island with two black chairs.
A covered outdoor area with a view of a water body and houses in the background.
A modern living room with a grey sofa, wooden coffee table, and a TV mounted on a white wall with a distressed wood panel design.

5. Luxury 3-Bed Condo in Storey Lake Resort - 3131

Luxury 3-Bed Condo in Storey Lake Resort - 3131
Kissimmee
United States
Matt G.
NZ$686
includes taxes & fees
26 Oct - 27 Oct
Luxury 3-Bed Condo in Storey Lake Resort - 3131
A modern living room with a flat-screen TV, a ceiling fan, a sofa, a coffee table, and a TV stand.
A large rectangular swimming pool with a surrounding deck, lounge chairs, and umbrellas.
A modern living room with a dining area, a sofa, a TV, and a ceiling fan.
A residential complex with a central swimming pool, multiple tennis courts, and a parking area.

6. 2306 SP - Disney Villa: 2BR, Pool, Near Magic!

2306 SP - Disney Villa: 2BR, Pool, Near Magic!
Four Corners
NZ$828
includes taxes & fees
19 Nov - 20 Nov
2306 SP - Disney Villa: 2BR, Pool, Near Magic!
A modern living room with a flat-screen TV, a sofa, a coffee table, and a ceiling fan.
A modern kitchen with wooden cabinets, a black refrigerator, a stove, and a microwave.
A kitchen with a coffee station, shelves with kitchenware, and a coffee maker.
A dining area with a wooden table, four matching stools, a decorative sign above the table, and a wall-mounted light switch.

7. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
NZ$336
includes taxes & fees
2 Nov - 3 Nov
Perfect Place for a Perfect Vacation
A living room with a grey sofa, a wooden table with a menu, a grey armchair with a leopard print pillow, and a view of a backyard through large windows.
Interior
A covered outdoor area with a white railing, a golf cart, and palm trees.
A golf cart parked near a miniature golf course with a clear sky and residential buildings in the background.

8. SPACIOUS 1 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2752

SPACIOUS 1 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2752
Kissimmee
United States
Alexis B.
NZ$413
includes taxes & fees
14 Nov - 15 Nov
SPACIOUS 1 BEDROOM HOUSE IN DISNEY AREA 5 STAR RATED MILL CREEK RESORT 2752
Pool
A modern living room with a glass coffee table, white sofas, a flat-screen TV mounted on a textured wall, a ceiling fan, and a floor lamp.
A modern kitchen with a central island, dining area with chairs, and a living area with a sofa and TV.
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

9. Perfect 2BD Family Condo w/ Balcony Near Disney

Perfect 2BD Family Condo w/ Balcony Near Disney
Kissimmee
NZ$546
includes taxes & fees
15 Nov - 16 Nov
Perfect 2BD Family Condo w/ Balcony Near Disney
A swimming pool with people swimming and lounging, surrounded by palm trees and a building with a tiled roof.
A beach volleyball court with a net, palm trees, and a body of water in the background.
A playground with a climbing structure, slides, and a turtle-shaped play area.
A dining area with a wooden table, white chairs, and a chandelier.

10. Superb Townhouse Newly Renovated 1.5 miles to Disney

Superb Townhouse Newly Renovated 1.5 miles to Disney
Kissimmee
United States
Sandy T.
NZ$348
includes taxes & fees
26 Oct - 27 Oct
Superb Townhouse Newly Renovated 1.5 miles to Disney
View all properties

Top Kissimmee Hotel Reviews

Explore a world of travel with Expedia