An aerial view of a residential area with numerous houses, roads, and several lakes.

Hotels in Windsor Hills

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Where to stay in Windsor Hills?

A resort with multiple swimming pools, palm trees, and lounge areas.

A modern living room with a sofa, coffee table, and dining area with chairs.

A sign for Windsor Hills Clubhouse surrounded by lush greenery and palm trees.

A modern kitchen with stainless steel appliances, a double sink, and a small potted plant.

1. Mickey s Hideaway Windsor Hills Resort

Windsor Hills

A pool with a waterfall feature, lounge areas, and a building with a green roof in the background.

A spacious lobby with high ceilings, chandeliers, a reception desk, and seating areas.

A landscaped area with a fountain, a pathway, and a building with balconies.

A golf course with a pond, a hotel with a green roof, and a highway in the background.

2. Hilton Vacation Club Mystic Dunes Orlando

0.8 km from Windsor Hills

Jeanette

$86

$132 total

includes taxes & fees

Oct 8 - Oct 9

A spacious dining area with a long table and multiple seating options, including booths and chairs.

A modern living room with a curved leather sofa, a round glass coffee table with a plant, and a chandelier with two decorative rings.

A hotel room with two beds, a nightstand with a lamp, and a painting on the wall.

A hotel entrance with a covered patio, columns, and a glass door leading inside.

3. Quality Inn & Suites By the Parks

1.5 km from Windsor Hills

Linda

$71

$81 total

includes taxes & fees

Oct 26 - Oct 27

A hotel with a pool, outdoor seating, and a sign for 'Galleria'.

A hotel room with a bed, desk, chair, and a TV on the wall.

An aerial view of a swimming pool with lounge chairs and a small waterfall feature.

A dining area with wooden tables and chairs, a reception desk, and a television screen.

4. Galleria Palms Hotel

1.8 km from Windsor Hills

Teeshila

$71

$103 total

includes taxes & fees

Oct 21 - Oct 22

A spacious lobby with a grand chandelier, modern seating, and a view of the outdoor area.

A pool area with a chandelier, a statue, and a view of the outside.

A resort pool area with a winding pool design, lounge chairs, and palm trees.

A spa entrance with a wooden facade, a sign indicating a sauna, and a patterned metal partition.

5. Kompose Boutique Resort at Theme Parks

1.8 km from Windsor Hills

Danai

$39

$88 total

includes taxes & fees

Oct 4 - Oct 5

A water park with slides and water features.

A gym with treadmills, exercise bikes, and weight machines.

A restaurant with blue chairs, wooden tables, and hanging blue and red lanterns.

A covered patio area with stone flooring, outdoor seating, and a view of a building with a sign.

6. Westgate Town Center Resort

0.9 km from Windsor Hills

Robert

$90

$137 total

includes taxes & fees

Oct 3 - Oct 4

A hotel entrance with a pool, palm trees, and a fountain.

A courtyard with a fire pit, surrounded by a brick wall, and a pool in the background.

A pool area with a gazebo, palm trees, and a building in the background.

A registration desk with a red and black counter, a large potted plant, and a mural on the wall.

7. Ramada by Wyndham Kissimmee Gateway

1.6 km from Windsor Hills

Raymon

$56

$84 total

includes taxes & fees

Oct 19 - Oct 20

A hotel with a central pool area, multiple water slides, and a surrounding pool.

A bar area with multiple shelves displaying wine bottles and glasses.

An outdoor patio area with seating and a restaurant sign.

8. Westgate Vacation Villas Resort

0.9 km from Windsor Hills

Laquaysha Crumity

$85

$130 total

includes taxes & fees

Oct 3 - Oct 4

A spacious lobby with a high ceiling, wooden beams, and a central fountain.

A water park with multiple slides and a swimming pool surrounded by lounge areas and umbrellas.

An aerial view of a resort with multiple swimming pools, a large central pool, and surrounding greenery.

A spacious lobby with high ceilings, exposed beams, and a tropical theme featuring palm trees and hanging lights.

9. Margaritaville Resort Orlando with H2O Waterpark

2.5 km from Windsor Hills

Eva

$129

$201 total

includes taxes & fees

Oct 21 - Oct 22

A hotel with a large building, a pond with a fountain, and palm trees.

A lobby with a stone wall, two orange armchairs, a green sofa, and a fireplace.

A hotel room with two beds, a desk, and a lamp.

A conference room with a long table, two chairs, and a TV screen.

10. The Adventure Hotel by the parks

1.9 km from Windsor Hills

Noemi

$56

$83 total

includes taxes & fees

Oct 7 - Oct 8

A breakfast bar with various food dispensers, a seating area with a table and chairs, and large windows with a view of greenery.

A swimming pool with clear blue water, surrounded by lounge chairs and yellow umbrellas.

A hotel room with a large window overlooking a swimming pool and a landscaped area with trees and a building in the background.

A lobby with a central seating area, wooden ceiling, and patterned carpet.

11. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

7.1 km from Windsor Hills

April

$89

$100 total

includes taxes & fees

Oct 27 - Oct 28

A modern interior with a kitchen area, a staircase, and a seating area with a black sofa.

A room with two black leather chairs, a large window with curtains, and a tiled floor.

A staircase with a patterned carpet leading to a landing.

A hotel room with a flat-screen TV mounted on the wall, a small table with a coffee maker, and a microwave on a cabinet.

12. Destiny Palms Hotel Maingate West

4 km from Windsor Hills

Raven

$57

$69 total

includes taxes & fees

Nov 1 - Nov 2

An aerial view of a curved swimming pool with lounge chairs and umbrellas around it.

A modern interior with a wooden counter, hanging pendant lights, and a blue door labeled "The Wilson".

A rooftop bar with outdoor seating, artificial grass, and colorful umbrellas overhead.

A hotel with a circular brick facade, multiple windows, and a central fountain.

13. Meliá Orlando Celebration

5.9 km from Windsor Hills

Heather

$57

$101 total

includes taxes & fees

Oct 11 - Oct 12

A spacious restaurant with high ceilings, hanging pendant lights, and a variety of seating arrangements.

A spacious lobby with a reception desk, seating area, and a decorative flower arrangement.

A spacious lobby with a leather sofa, a bar area with stools, and a seating area with tables and chairs.

An outdoor dining area with round tables covered in foliage, surrounded by chairs, and a stone wall with plants.

14. Embassy Suites by Hilton Orlando Lake Buena Vista South

11.5 km from Windsor Hills

Kelvin

$90

$102 total

includes taxes & fees

Oct 18 - Oct 19

An outdoor patio area with a fire pit, yellow and blue seating, and a covered section with a pergola.

A modern hotel room with a dining area, a living space with a sofa and coffee table, and a kitchenette.

A hotel with a prominent "HOME 2" sign, a stone facade, and an arched entrance.

A hotel pool area with multiple lounge chairs and umbrellas, a water slide, and palm trees.

15. Home2 Suites by Hilton Orlando at Flamingo Crossings

7 km from Windsor Hills

Rogelio

$98

$110 total

includes taxes & fees

Oct 25 - Oct 26

A large hotel with multiple floors, a central courtyard, and a reflective water feature.

A covered outdoor seating area with tables and chairs, a ceiling fan, and a view of a pool and buildings in the background.

A modern lobby with a large fireplace, comfortable seating, and a well-lit ceiling.

A hotel pool area with lounge chairs, a fire pit, and a large pool.

16. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

7 km from Windsor Hills

Josefina

$110

$124 total

includes taxes & fees

Oct 26 - Oct 27

An outdoor patio area with wicker furniture, a fire feature, and umbrellas.

A spacious lobby with a reception desk, seating area, and a bar.

A poolside area with lounge chairs, a table, and umbrellas.

A hotel room with two beds, a TV, a desk, and a window with curtains.

17. Nobile Hotel Parkway at Celebration Orlando

6.5 km from Windsor Hills

Elmo

$55

$93 total

includes taxes & fees

Oct 31 - Nov 1

A water play area with a slide and water jets.

A modern hotel lobby with a reception desk, seating area, and a dining section.

A modern living room with a large flat-screen TV, built-in shelving, and a seating area.

A modern breakfast area with a self-serve station, including yogurt, eggs, and milk.

18. Holiday Inn Express & Suites Clermont Se West Orlando by IHG

6.8 km from Windsor Hills

Dorothy

$91

$101 total

includes taxes & fees

Nov 1 - Nov 2

A hotel with a central entrance, palm trees, and a clear sky.

A hotel room with two beds, a large window with curtains, an air conditioning unit, and a bedside table with a lamp.

A hotel lobby with seating areas, a reception desk, and a Coca-Cola refrigerator.

A hotel room with a bed, a sofa, a coffee table, and a desk. There are three framed pictures on the wall.

19. Comfort Suites Maingate East

8.2 km from Windsor Hills

Ronald

$71

$81 total

includes taxes & fees

Nov 1 - Nov 2

An aerial view of a resort with a large swimming pool surrounded by palm trees and lounge chairs.

A pathway leading to a body of water with a fountain, surrounded by palm trees and a building with multiple floors.

A hotel with multiple floors, a swimming pool, and palm trees.

A spacious living room with a large window, a sofa set, a coffee table, and a television.

20. Wyndham Grand Orlando Resort Bonnet Creek

7.3 km from Windsor Hills

Alexandra

$124

$187 total

includes taxes & fees

Oct 29 - Oct 30

View all properties

Go beyond your typical stay in Windsor Hills

Our prices for hotels in Kissimmee are cheapest in August

Check out reviews of Windsor Hills hotels guests love

Galleria Palms Hotel

Kissimmee

10/10 Exceptional

Rebecca

Quality Inn & Suites By the Parks

Kissimmee

10/10 Exceptional

Deshawn

A modern hotel with a red carpet leading to the entrance, a wooden walkway, and a clear view of the building's facade.

A reception desk with a wooden backdrop and a green wall display.

A modern hotel room with a large bed, a blue sofa, a small round table, and a large window offering a view of trees.

A modern dining area with bar seating, round tables, and chairs.

EVEN Hotel Orlando International Airport by IHG

Airport North

10/10 Exceptional

Carol

Embassy Suites by Hilton Orlando Lake Buena Vista South

Kissimmee

10/10 Exceptional

Chris

Westgate Town Center Resort

Kissimmee

10/10 Exceptional

Robert

Westgate Vacation Villas Resort

Kissimmee

10/10 Exceptional

Annette

A reception desk area with a neon sign reading "TRYP Orlando" and a modern wooden ceiling.

A hotel room with two beds, a TV, a desk, and a mural with palm trees and text.

A modern dining area with a long wooden table and black chairs, a bar area with a patterned backsplash, and a view of the outside through large windows.

A modern hotel with a swimming pool, outdoor seating, and a well-lit facade.

TRYP by Wyndham Orlando

International Drive District

10/10 Exceptional

Jonathan

Meliá Orlando Celebration

Celebration

10/10 Exceptional

Deborah

A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.

A hotel with a swimming pool, multiple parking spaces, and a view of the surrounding area.

A swimming pool with red umbrellas, lounge chairs, and a poolside table.

An outdoor seating area with wicker furniture, a central wooden table, and a red brick wall with potted plants.

Seasons Florida Resort

Kissimmee

10/10 Exceptional

I don’t want to leave a good review because this place is a hidden gem and I don’t want the secret to get out! We stayed for a week, the main purpose was to go to Disney. From hotel door to Magic Kingdom gate was 15-20 minutes. There is a Target 3 minutes driving distance and the cleanest Waffle House with the nicest staff is across the street. You will need a car to access either of these. The staff for this hotel could not have been nicer. This is a very very basic no frills hotel. If...

Michelle

A spacious lobby with a central reception desk, two escalators, and a high ceiling with large chandeliers.

A hotel pool area with sun loungers and umbrellas, a clear blue pool, and a multi-story building in the background.

A Starbucks coffee shop with a counter, bar stools, and a seating area with tables and chairs.

A large hotel with a central courtyard, a swimming pool, and multiple parking spaces.

Florida Hotel & Conference Center in the Florida Mall

Orlando

10/10 Exceptional

Monica

A multi-story hotel with a prominent 'Hyatt House' sign, a covered entrance, and a parking lot with landscaping.

A reception desk with a wooden finish, a blue wall with a leaf pattern, and a white door.

A modern kitchen with grey cabinets, a white countertop, and a central island with a chair.

Hyatt House Orlando International Drive

International Drive District

10/10 Exceptional

jordan

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Bay Lake

10/10 Exceptional

We had an excellent stay! The hotel is clean, modern, and very well-appointed, with comfortable rooms that made us feel right at home. Traveling with our toddler, we found everything to be exceptional—the accommodations were spacious and family-friendly. The free breakfast was a fantastic bonus, with a variety of options, including some vegan-friendly choices, which we really appreciated. The staff was welcoming and attentive, ensuring we had everything we needed for a great stay. We would...

Nicolette

A modern dining area with round tables and chairs, a long counter, and a patterned rug.

A snack and beverage display with a 'Welcome to Orlando' sign.

A hotel room with a grey sofa, a small table, a desk with a chair, a mirror, and a picture on the wall.

A hotel room with a bed, desk, and chair, a mirror, and a door leading to another room.

Hampton Inn & Suites Orlando Intl Dr N

International Drive District

10/10 Exceptional

Pui chi

A hotel with a large pool, palm trees, and a waterfall feature.

A bar area with a variety of seating options, including patterned chairs and stools, a bar counter with bottles, and a large mirror on the wall.

A hotel lobby with a reception desk, seating area, and a staircase leading to upper floors.

A spacious dining area with a long table set for a meal, surrounded by chairs.

Caribe Royale Orlando, WorldHotels Elite

Orlando

10/10 Exceptional

While this resort is beautiful and clean we had a few issues. First, it would have been wonderful to know that they will rent out many of the common areas (pool), restaurants and bars for private events. There was an event just about every night we during our 7 day stay. Some nights we were not able to use the bridge to cross to our villa so we (3 adults, 3 small children) had to walk around extra 4 buildings, other nights we were not able to use the main pool, sports bar or pool side bar. This...

Shannon

A large pool with lounge chairs and palm trees, surrounded by a modern building with a patterned facade.

A hotel room with a large window, a bed, a sofa, a desk, and a painting on the wall.

A hallway with two white doors, a polka dot wall, and a blue wall with illuminated numbers.

A modern lounge area with seating, a colorful wall, and a ceiling with circular lights.

Universal's Terra Luna Resort

Orlando

10/10 Exceptional

Ashlin

A Holiday Inn hotel with a registration area, multiple floors, and a well-lit entrance.

A rectangular pool with a surrounding brick walkway, lounge chairs, and palm trees.

A modern interior with a sectional sofa, a green armchair, and a glass table.

A modern hotel lobby with a reception desk, a breakfast area, and a seating area with tables and chairs.

Holiday Inn Orlando International Dr-ICON by IHG

International Drive District

10/10 Exceptional

Julie

A hotel room with a large bed, a smaller bed, a desk, and a chair. There is a decorative item on the bed and a rug on the floor.

A modern interior with a white spiral staircase, a large Christmas tree, and a dining area with white furniture.

A swimming pool with clear water, surrounded by a white fence and shaded by several white umbrellas.

A modern kitchen with white countertops, stainless steel appliances, and hanging plants.

Palazzo Lakeside Hotel

Kissimmee

10/10 Exceptional

Lorraine

A pool area with multiple pools, lounge chairs, and a dining setup.

A spacious lobby with a reception desk, a staircase, and a large digital screen.

A hotel room with a large window offering a view of a cityscape, including a prominent white building and a body of water.

A hotel room with a large bed, a desk, a chair, a small table, and a view of the cityscape.

Hilton Orlando Lake Buena Vista - Disney Springs® Area

Lake Buena Vista

10/10 Exceptional

Mary

A large outdoor swimming pool with multiple lanes, surrounded by lounge chairs and umbrellas.

A spacious lobby with a wooden floor, large decorative chandeliers, and potted plants.

A spacious lobby with a wooden floor, a grey sofa set, a brown ottoman, and a staircase with a wooden railing.

A hotel room with a bed, a desk, a television, and a large window with a city view.

Wyndham Lake Buena Vista – Disney Springs® Area

Lake Buena Vista

10/10 Exceptional

Dawn

A hotel pool area with lounge chairs and umbrellas, surrounded by palm trees and modern buildings.

A modern hotel with a distinctive blue and white facade, featuring a large mural and a curved entrance canopy.

A spacious lobby with a high ceiling, large windows, and modern seating areas.

A modern hotel lobby with a central reception desk, multiple screens displaying menus, and a ceiling with a unique design.

Universal's Endless Summer Resort - Surfside Inn and Suites

International Drive District

10/10 Exceptional

The beginning of a great stay started with Carmen at the front desk. We felt welcomed, informed and appreciated. I read reviews about the hot water, but we had no problem; the shower was great with adequate hot water. The rooms were clean and cleaned daily. The mattresses isn’t plush but I slept well. The shuttle to City Walk and Universal Studios theme parks and early entry into parks was a plus. The restaurant and Starbucks on property were convenient. The property is in a great location and...

Tanya

Hotels in Windsor Hills

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Windsor Hills?

1. Mickey s Hideaway Windsor Hills Resort

2. Hilton Vacation Club Mystic Dunes Orlando

3. Quality Inn & Suites By the Parks

4. Galleria Palms Hotel

5. Kompose Boutique Resort at Theme Parks

6. Westgate Town Center Resort

7. Ramada by Wyndham Kissimmee Gateway

8. Westgate Vacation Villas Resort

9. Margaritaville Resort Orlando with H2O Waterpark

10. The Adventure Hotel by the parks

11. Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

12. Destiny Palms Hotel Maingate West

13. Meliá Orlando Celebration

14. Embassy Suites by Hilton Orlando Lake Buena Vista South

15. Home2 Suites by Hilton Orlando at Flamingo Crossings

16. Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

17. Nobile Hotel Parkway at Celebration Orlando

18. Holiday Inn Express & Suites Clermont Se West Orlando by IHG

19. Comfort Suites Maingate East

20. Wyndham Grand Orlando Resort Bonnet Creek

Go beyond your typical stay in Windsor Hills

Price trends for hotels in Kissimmee

October

Check out reviews of Windsor Hills hotels guests love

Galleria Palms Hotel

10/10 Exceptional

Quality Inn & Suites By the Parks

10/10 Exceptional

EVEN Hotel Orlando International Airport by IHG

10/10 Exceptional

Embassy Suites by Hilton Orlando Lake Buena Vista South

10/10 Exceptional

Westgate Town Center Resort

10/10 Exceptional

Westgate Vacation Villas Resort

10/10 Exceptional

TRYP by Wyndham Orlando

10/10 Exceptional

Meliá Orlando Celebration

10/10 Exceptional

Seasons Florida Resort

10/10 Exceptional

Florida Hotel & Conference Center in the Florida Mall

10/10 Exceptional

Hyatt House Orlando International Drive

10/10 Exceptional

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

10/10 Exceptional

Hampton Inn & Suites Orlando Intl Dr N

10/10 Exceptional

Caribe Royale Orlando, WorldHotels Elite

10/10 Exceptional

Universal's Terra Luna Resort

10/10 Exceptional

Holiday Inn Orlando International Dr-ICON by IHG

10/10 Exceptional

Palazzo Lakeside Hotel

10/10 Exceptional

Hilton Orlando Lake Buena Vista - Disney Springs® Area

10/10 Exceptional

Wyndham Lake Buena Vista – Disney Springs® Area

10/10 Exceptional

Universal's Endless Summer Resort - Surfside Inn and Suites

10/10 Exceptional