Windermere Holiday Rentals, Orlando: Private House Rentals

A lakeside community with houses and boats.

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Our top choices for Windermere hotels

A staircase with white railings and wooden steps leading to an upper floor.

1. Rustic Hideaway - Great Location + Pet Friendly!

Windermere

Mercedes

3.711.171 ₫

15.272.136 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with stainless steel appliances, a granite island, and a built-in oven.

A modern living room with a sofa, coffee table, and a bookshelf filled with books.

A modern living room with a dining area, featuring a marble table, orange chairs, a sofa, and a ceiling fan.

A spacious living area with a wooden rocking chair, a white console table, and a dining area in the background.

2. The Farm House - Great Location + Pet Friendly!

Windermere

4.125.827 ₫

14.662.787 ₫ total

includes taxes & fees

15 Oct - 16 Oct

A hotel pool area with lounge chairs and umbrellas, surrounded by tall buildings and a sunset sky.

An outdoor patio area with wicker furniture, red accents, and palm trees.

A water play area with multiple fountains and colorful play structures.

A modern hotel lobby with seating areas, tables, and decorative wall panels.

3. Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

Brianne

4.738.814 ₫

5.331.166 ₫ total

includes taxes & fees

25 Oct - 26 Oct

An outdoor pool area with a covered seating area, surrounded by palm trees and a modern building in the background.

A hotel room with two beds, a desk, a TV, and a large window offering a city view.

A hotel with a large pool, palm trees, and modern buildings.

An indoor arcade with racing game machines and a seating area with red and black racing seats.

4. DoubleTree by Hilton at the Entrance to Universal Orlando

Florida Center

Kristal

2.401.117 ₫

2.701.257 ₫ total

includes taxes & fees

29 Oct - 30 Oct

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.

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

Bay Lake

Lauren

1.960.545 ₫

2.205.613 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A swimming pool area with multiple water slides and palm trees.

A child sitting on a blue inflatable pool in a hotel room with a large window, a red armchair, and a suitcase.

A modern hotel room with a large window, a sofa, a TV, a desk, and a bed.

A spacious indoor atrium with high ceilings, palm trees, and modern seating areas.

6. Universal's Cabana Bay Beach Resort

Florida Center

Ruben

3.889.800 ₫

4.376.026 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A modern hotel lobby with a reception desk, seating area, and a large chandelier.

A modern hotel lobby with a reception desk, multiple TVs, a chandelier, and a seating area.

A modern bar area with a long counter, multiple stools, and a kitchen area with wooden cabinets and a TV.

A pool area with lounge chairs and a building with multiple balconies in the background.

7. DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

International Drive District

Niaris

1.637.891 ₫

1.842.628 ₫ total

includes taxes & fees

4 Nov - 5 Nov

A breakfast bar with a chalkboard displaying food items and utensils.

A hotel room with a bed, a desk with a flat-screen TV, a chair, a lamp, and a window with curtains.

A reception area with a wooden reception desk, a large framed picture of a Ferris wheel, and a vending machine.

A hotel room with two beds, each with white linens, a headboard, bedside tables with lamps, and a carpeted floor.

8. Hampton Inn closest to Universal Orlando

Florida Center

Jackie

1.921.671 ₫

2.161.880 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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 room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.

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

Bay Lake

Camille

2.224.889 ₫

2.503.000 ₫ total

includes taxes & fees

4 Nov - 5 Nov

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.

10. Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

Ellen

2.528.883 ₫

2.844.993 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A spacious room with wooden flooring, large windows, and a green carpet. There are two orange rocking chairs and a round table.

A modern cafe with wooden tables and chairs, a counter with a yogurt display, and large windows overlooking greenery.

A modern hotel lobby with a seating area, a small kitchenette, and vending machines.

A reception desk with a modern design, featuring a wooden finish and a green carpet.

11. Spark by Hilton Orlando near Universal

Florida Center

Jessica

2.180.831 ₫

2.453.434 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

A conference room with multiple tables and chairs, a patterned carpet, and modern lighting fixtures.

12. Holiday Inn Orlando International Dr-ICON by IHG

International Drive District

Sherry

1.891.868 ₫

2.517.091 ₫ total

includes taxes & fees

12 Nov - 13 Nov

A modern hotel lobby with a reception desk, seating area with yellow and blue chairs, and large windows offering views of the outdoors.

A modern hotel lobby with a central counter, a refrigerator stocked with beverages, and shelves with snacks and condiments.

A modern restaurant with a bar area, seating with yellow and black upholstered booths, and pendant lighting.

A spacious lobby with modern seating, large windows, and decorative lighting.

13. Hilton Garden Inn Millenia near Universal Orlando Resort

Florida Center

Juan A

2.316.372 ₫

2.605.918 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

14. Wyndham Grand Orlando Resort Bonnet Creek

Orlando

Anthony

3.213.584 ₫

4.839.814 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A multi-story hotel with a swimming pool, parking, and a landscaped area.

A hotel room with two beds, a desk, a chair, a large window, and a view of buildings and palm trees.

A modern hotel lobby with a reception desk, seating area with colorful chairs, a blue sofa, and a flat-screen TV mounted on the wall.

A hotel room with two beds, a desk, and a view of the outdoors.

15. Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG

Orlando

Abi Carolina Fornino

2.151.028 ₫

2.419.906 ₫ total

includes taxes & fees

28 Oct - 29 Oct

A pool area with people swimming and relaxing.

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

A hotel with a modern design, featuring a large building with multiple floors and a covered outdoor area with seating.

A spacious lobby with a high ceiling, seating areas, and a bar.

16. Universal's Endless Summer Resort - Dockside Inn and Suites

Florida Center

Stephanie

3.084.004 ₫

3.469.504 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A hotel room with a sofa, two beds, a table, and a view of buildings.

A self-service kiosk area with refrigerated beverage dispensers and snack shelves.

A multi-story hotel with a parking lot, a covered entrance, and a landscaped area with palm trees.

An outdoor dining area with multiple tables and chairs, ceiling fans, and a view of the surrounding greenery.

17. City Express by Marriott Orlando International Drive

International Drive District

Paul

2.401.117 ₫

2.701.258 ₫ total

includes taxes & fees

3 Nov - 4 Nov

An outdoor infinity pool with a clear view of the cityscape, surrounded by lounge chairs and a bar area.

A pool table in a modern indoor space with large windows, a seating area, and a television.

An outdoor dining area with tables and chairs, a bar with shelves of bottles, and a view of the landscape.

A modern lobby with large windows, a fireplace, and a flat-screen TV displaying a news channel.

18. Cambria Hotel Orlando Universal Blvd

International Drive District

Wendy

2.371.832 ₫

2.979.303 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A clear blue pool with lounge chairs and umbrellas, surrounded by palm trees and a building with a balcony.

A grocery store interior with refrigerated sections, a checkout counter, and a beverage section.

An outdoor patio with wicker furniture, green umbrellas, and brick walls.

19. Rosen Inn International

International Drive District

Edgardo Joel

1.982.341 ₫

2.230.133 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A breakfast area with a counter displaying hard-boiled eggs, fruits, and muffins. There are two stools and a sign reading "TOP IT BREAKFAST".

A snack kiosk with various packaged snacks and a beverage dispenser.

A rooftop bar with round tables, a pool, and outdoor seating.

20. Tru By Hilton Orlando Convention Center Area, FL

International Drive District

Talore

2.180.831 ₫

2.453.434 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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Stay near popular Windermere attractions

Tibet Butler Preserve

Explore 3.6 miles of trails through Florida's diverse ecosystems at this tranquil preserve near Orlando. The Vera Carter Environmental Centre offers fascinating exhibits about local wildlife and habitats.

See properties

Isleworth Golf and Country Club

This exclusive, members-only sanctuary features an Arnold Palmer-designed championship golf course. Residents enjoy lavish amenities while rubbing shoulders with professional athletes and celebrities who call Isleworth home.

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Lake Bessie

Commune with nature and explore the great outdoors at Lake Bessie during your travels in Windermere. Amble around the area's beaches or visit its shops.

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Learn more about Windermere

Nestled among pristine lakes, this charming town offers a peaceful escape with upscale golf courses and country clubs. Nature lovers can explore the Tibet-Butler Preserve's trails, while four-legged friends enjoy romping at Buena Vista Place Dog Park.

See all hotels in Windermere

Top Windermere Hotel Reviews

Universal's Cabana Bay Beach Resort

10/10 Excellent

"I loved the layout of the room. The food on-site was not overpriced at all, and plentiful servings. Every encounter with staff was pleasant."

Seasons Florida Resort

8/10 Good

"Esta muy bueno por el precio serca de todo limpio y fueron amables me volveria a quedar"

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

10/10 Excellent

"Booked it for the reasonable price and will be coming back because it was a hit! The beds were comfortable. The rooms were clean and the AC was crisp. And breakfast is included?! We will be back!"

The Grove Resort & Water Park Orlando

10/10 Excellent

"Buen hotel para pasarlo en familia muchas cosas para hacer recomendado !! Lo único a mejorar es un poco los olores de la limpieza pero lo demás todo bien el personal muy amable recomendado 8.5/10"

Rosen Inn Lake Buena Vista

10/10 Excellent

"Clean room and friendly staff"

Evermore Orlando Resort

10/10 Excellent

"Our family had an amazing time at Evermore! The staff went out of their way to make our daughter’s birthday truly memorable! We can’t wait to come back and stay again!"

Holiday Inn Resort Orlando Suites - Waterpark by IHG

10/10 Excellent

"Great waterpark for my whole family. The rooms were clean and comfortable. Overall wonderful experience. My biggest complaint is charging guest a daily parking fee."

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent

"El proceso de check in fue rápido. Hay personal bilingüe disponible en el Front Desk y en la Cafetería Pier 8"

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent

"This was our first time at Westgate Lakes Resort, and we will definitely come back! We had an amazing and HUGE 2 bedroom unit that overlooked a lake, and it was also very convenient to one of the pools. Also close to the shops, restaurants and main building. We unfortunately had some bad weather and couldn't enjoy the water park, but I went to the fitness center and it was outstanding! All of the staff was helpful, the beds were super comfortable and I even got to enjoy a bubble bath in the huge jacuzzi tub in the master bedroom. There were ample towels, hand towels, toilet paper, paper towels etc. I highly recommend this resort, we were 15 minutes from Universal Theme Parks, as well as only a few minutes from International Drive and other restaurants and the Kia Center. We'll definitely come back, as we visit Orlando often! The only slight negative at all was the check in Friday night was very busy and took a little bit, and also our key stopped working before our check out time but we were able to text the front desk and they set up for us to reactivate our key from the building. Very efficient and nice staff though, Jennica at the front was wonderful and the assistance we got with our bags was so appreciated from the person who also led us to our building. Looking forward to our next trip to hopefully be able to stay at Westgate again!"

More cheap stays in Windermere

Seasons Florida Resort

4736 W Irlo Bronson Hwy Memorial Kissimmee FL

1.162.333 ₫

1.319.247 ₫ total

15 Oct - 16 Oct

includes taxes & fees

9/10 Wonderful! (4,034 reviews)

Baymont by Wyndham Orlando North Millenia

2500 33Rd Street Orlando FL

1.259.518 ₫

1.619.491 ₫ total

18 Oct - 19 Oct

includes taxes & fees

7/10 Good! (2,391 reviews)

Galleria Palms Hotel

3000 Maingate Ln Kissimmee FL

1.551.072 ₫

2.333.756 ₫ total

27 Oct - 28 Oct

includes taxes & fees

9/10 Wonderful! (3,864 reviews)

Spark by Hilton Orlando near Universal

5635 Windhover Dr Orlando FL

2.180.831 ₫

2.453.434 ₫ total

2 Nov - 3 Nov

includes taxes & fees

8.8/10 Excellent! (1,770 reviews)

Hampton Inn Orlando-International Airport

5767 T.G. Lee Blvd. Orlando FL

2.511.260 ₫

2.825.169 ₫ total

26 Oct - 27 Oct

includes taxes & fees

9/10 Wonderful! (2,185 reviews)

AC Hotel by Marriott Orlando Downtown

333 South Garland Avenue Orlando FL

4.341.837 ₫

4.884.566 ₫ total

30 Oct - 31 Oct

includes taxes & fees

Hotels in Windermere with star rating

Frequently asked questions

What's the weather like in Windermere?

The hottest months are usually August and July, with an average temperature of 27°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Windermere are August, July, September and June, with each month seeing an average of 194 mm of rainfall.

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Book Hotels in Windermere on Expedia.com

Find hotels in Windermere, FL from 1.319.247 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Windermere

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Windermere hotels

1. Rustic Hideaway - Great Location + Pet Friendly!

2. The Farm House - Great Location + Pet Friendly!

3. Drury Plaza Hotel Orlando - Disney Springs Area

4. DoubleTree by Hilton at the Entrance to Universal Orlando

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

6. Universal's Cabana Bay Beach Resort

7. DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

8. Hampton Inn closest to Universal Orlando

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

10. Home2 Suites by Hilton Orlando at Flamingo Crossings

11. Spark by Hilton Orlando near Universal

12. Holiday Inn Orlando International Dr-ICON by IHG

13. Hilton Garden Inn Millenia near Universal Orlando Resort

14. Wyndham Grand Orlando Resort Bonnet Creek

15. Holiday Inn Express & Suites Orlando - Lake Buena Vista by IHG

16. Universal's Endless Summer Resort - Dockside Inn and Suites

17. City Express by Marriott Orlando International Drive

18. Cambria Hotel Orlando Universal Blvd

19. Rosen Inn International

20. Tru By Hilton Orlando Convention Center Area, FL

Stay near popular Windermere attractions

Tibet Butler Preserve

Isleworth Golf and Country Club

Lake Bessie

Learn more about Windermere

Top Windermere Hotel Reviews

Universal's Cabana Bay Beach Resort

Seasons Florida Resort

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

The Grove Resort & Water Park Orlando

Rosen Inn Lake Buena Vista

Evermore Orlando Resort

Holiday Inn Resort Orlando Suites - Waterpark by IHG

Universal's Endless Summer Resort - Dockside Inn and Suites

Westgate Lakes Resort & Spa Universal Studios Area

More cheap stays in Windermere

Seasons Florida Resort

Baymont by Wyndham Orlando North Millenia

Galleria Palms Hotel

Spark by Hilton Orlando near Universal

Hampton Inn Orlando-International Airport

AC Hotel by Marriott Orlando Downtown

Hotels in Windermere with star rating

Frequently asked questions

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