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

3.722.341 ₫

15.318.102 ₫ total

includes taxes & fees

8 Oct - 9 Oct

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

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

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

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

2. Drury Plaza Hotel Orlando - Disney Springs Area

Lake Buena Vista

Brianne

4.197.771 ₫

4.722.493 ₫ total

includes taxes & fees

28 Oct - 29 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 lobby with a central seating area, wooden ceiling, and patterned carpet.

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

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

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

Bay Lake

Deidra

2.313.466 ₫

2.602.649 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A spacious lobby with a reception desk, leather sofas, and a large star-patterned floor design.

A hotel entrance with a sign reading "Wingate by Wyndham."

A gym with treadmills, elliptical machines, and weight equipment.

A spacious dining area with multiple tables and chairs, a central pillar, and a kitchen area in the background.

4. Wingate by Wyndham Convention Ctr Closest Universal Orlando

Florida Center

Leonardo

2.585.103 ₫

2.908.242 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

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

5. Home2 Suites by Hilton Orlando at Flamingo Crossings

Bay Lake

Roderic

2.536.495 ₫

2.853.556 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A hotel reception area with two computer workstations, a printer, and a framed sign.

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

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

6. Hampton Inn closest to Universal Orlando

Florida Center

Jackie

2.057.165 ₫

2.314.310 ₫ total

includes taxes & fees

2 Nov - 3 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

1.642.821 ₫

1.848.175 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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.

8. Universal's Cabana Bay Beach Resort

Florida Center

Lenny

3.899.100 ₫

4.386.487 ₫ total

includes taxes & fees

3 Nov - 4 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 hotel room with a sofa, armchair, and a large window with a view of a swimming pool and hotel buildings.

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

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

Bay Lake

Camille

2.729.370 ₫

3.070.542 ₫ 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.

10. Spark by Hilton Orlando near Universal

Florida Center

Taylor

2.110.193 ₫

2.373.967 ₫ total

includes taxes & fees

13 Oct - 14 Oct

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 view through a large window of a resort with a pool, palm trees, and a building in the background.

11. Wyndham Grand Orlando Resort Bonnet Creek

Orlando

Anthony

3.223.256 ₫

4.854.380 ₫ total

includes taxes & fees

29 Oct - 30 Oct

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

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

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

A modern Hilton Garden Inn with a pool area, a covered entrance, and a parking lot.

12. Hilton Garden Inn Millenia near Universal Orlando Resort

Florida Center

Juan A

2.122.215 ₫

2.387.493 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with lounge chairs and palm trees, surrounded by a building with large windows.

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

Two high-rise buildings with reflections in a calm body of water, surrounded by greenery and palm trees.

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

13. DoubleTree by Hilton at the Entrance to Universal Orlando

Florida Center

Kristal

2.408.344 ₫

2.709.387 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a bed, a desk, a chair, a sofa, and a TV.

A corridor with a neon sign reading "Marketplace," vending machines, and shelves stocked with snacks and beverages.

A hotel with a modern facade, a central entrance, and a parking area.

A bakery counter with pastries, a coffee machine, and a sign reading "Happy Customers".

14. Pestana Orlando Suites - Lake Buena Vista

Orlando

Tracy

2.183.496 ₫

2.794.355 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A large outdoor swimming pool with multiple water features and lounge areas.

A spacious lobby with a high ceiling, large chandeliers, and a central seating area.

A bakery counter with a variety of pastries and a menu board above it.

A modern bar area with a bar counter, seating, and hanging light fixtures.

15. Wyndham Garden Lake Buena Vista – Disney Springs® Area

Lake Buena Vista

Arnelis

2.578.605 ₫

3.953.688 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A hotel lobby with a long corridor, modern lighting, and large abstract wall art.

16. Hyatt Regency Grand Cypress

Orlando

linda

4.185.034 ₫

6.170.325 ₫ total

includes taxes & fees

16 Oct - 17 Oct

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

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

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.

17. City Express by Marriott Orlando International Drive

International Drive District

Paul

1.855.972 ₫

2.087.968 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A pool area with people swimming and relaxing.

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

A spacious lobby with a central reception desk, a large mural, and a modern ceiling design.

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

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

Florida Center

Jorge

3.665.154 ₫

4.123.299 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A hotel room with a large bed, a sofa, a small table, and a TV.

A lobby with two patterned armchairs, a central coffee table, and three framed artworks on the wall.

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

A modern hotel room with a blue accent wall, a large bed, a sofa, a small table, and a TV.

19. Hyatt Place Orlando / I-Drive / Convention Center

International Drive District

Kiara

2.183.496 ₫

2.456.434 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

20. Rosen Inn International

International Drive District

Bob

1.988.281 ₫

2.236.815 ₫ total

includes taxes & fees

13 Oct - 14 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.

See properties

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

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

10/10 Excellent

"La locación"

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent

"It’s home :)"

Universal's Endless Summer Resort - Dockside Inn and Suites

10/10 Excellent

"Very clean, new Universal hotel. Both of the pools were large and easily accessed. The food court, room service options and on site Starbucks were incredibly convenient. Will definitely stay again!"

Westgate Lakes Resort & Spa Universal Studios Area

10/10 Excellent

"La habitación era maravillosa, la vista espectacular. Una muy buena ubicación. El lugar en sí nos encantó. Volveremos sin duda. Gracias"

Hyatt Regency Orlando International Airport

10/10 Excellent

"I can only reiterate the comments of others......it is right inside the airport terminal, and for those travelling from Terminal A and B, it is perfect for an early departure.....(Terminal C, is newer, and more remote)."

Walt Disney World Dolphin

10/10 Excellent

"Great food and staff"

Evermore Orlando Resort

10/10 Excellent

"The staff is unbelievably friendly. We loved our stay! The rooms were a great size too. Well worth it!"

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent

"Absolutely worth the price, exceeded expectations by far"

DoubleTree by Hilton at the Entrance to Universal Orlando

10/10 Excellent

"Very clean, quiet, and easy access to Universal Studios!"

More cheap stays in Windermere

Seasons Florida Resort

4736 W Irlo Bronson Hwy Memorial Kissimmee FL

1.206.382 ₫

1.369.244 ₫ total

29 Oct - 30 Oct

includes taxes & fees

Baymont by Wyndham Orlando North Millenia

2500 33Rd Street Orlando FL

1.224.544 ₫

1.580.671 ₫ total

21 Oct - 22 Oct

includes taxes & fees

7/10 Good! (2,363 reviews)

Spark by Hilton Orlando near Universal

5635 Windhover Dr Orlando FL

2.110.193 ₫

2.373.967 ₫ total

13 Oct - 14 Oct

includes taxes & fees

8.8/10 Excellent! (1,747 reviews)

Galleria Palms Hotel

3000 Maingate Ln Kissimmee FL

1.692.210 ₫

2.495.672 ₫ total

13 Oct - 14 Oct

includes taxes & fees

9/10 Wonderful! (3,846 reviews)

Hampton Inn Orlando-International Airport

5767 T.G. Lee Blvd. Orlando FL

2.429.919 ₫

2.733.659 ₫ total

26 Oct - 27 Oct

includes taxes & fees

9/10 Wonderful! (2,194 reviews)

AC Hotel by Marriott Orlando Downtown

333 South Garland Avenue Orlando FL

3.957.196 ₫

4.451.846 ₫ total

18 Oct - 19 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 1.369.244 ₫

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. Drury Plaza Hotel Orlando - Disney Springs Area

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

4. Wingate by Wyndham Convention Ctr Closest Universal Orlando

5. Home2 Suites by Hilton Orlando at Flamingo Crossings

6. Hampton Inn closest to Universal Orlando

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

8. Universal's Cabana Bay Beach Resort

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

10. Spark by Hilton Orlando near Universal

11. Wyndham Grand Orlando Resort Bonnet Creek

12. Hilton Garden Inn Millenia near Universal Orlando Resort

13. DoubleTree by Hilton at the Entrance to Universal Orlando

14. Pestana Orlando Suites - Lake Buena Vista

15. Wyndham Garden Lake Buena Vista – Disney Springs® Area

16. Hyatt Regency Grand Cypress

17. City Express by Marriott Orlando International Drive

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

19. Hyatt Place Orlando / I-Drive / Convention Center

20. Rosen Inn International

Stay near popular Windermere attractions

Tibet Butler Preserve

Isleworth Golf and Country Club

Lake Bessie

Learn more about Windermere

Top Windermere Hotel Reviews

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Drury Plaza Hotel Orlando - Disney Springs Area

Universal's Endless Summer Resort - Dockside Inn and Suites

Westgate Lakes Resort & Spa Universal Studios Area

Hyatt Regency Orlando International Airport

Walt Disney World Dolphin

Evermore Orlando Resort

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

More cheap stays in Windermere

Seasons Florida Resort

Baymont by Wyndham Orlando North Millenia

Spark by Hilton Orlando near Universal

Galleria Palms Hotel

Hampton Inn Orlando-International Airport

AC Hotel by Marriott Orlando Downtown

Hotels in Windermere with star rating

Frequently asked questions

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