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Aug 15 - Aug 17
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Browse Select Windermere Cottages

Orlando Lakefront Tiny House Community
Relax in a serene outdoor space with a deck overlooking a tranquil body of water, surrounded by lush greenery.

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (327)
"We enjoyed our stay."
The price is CA $89
CA $201 total
includes taxes & fees
Sep 8 - Sep 9
Orlando Lakefront Tiny House Community
Lafitte's Landing Lakeview Cottage - Lakefront!
House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage) | Property grounds

Lafitte's Landing Lakeview Cottage - Lakefront!

3.0 star property
10.0 out of 10, Exceptional, (7)
"Beautiful Cottage and enjoyed the back deck overlooking the lake. Great family vacation spot."
Lafitte's Landing Lakeview Cottage - Lakefront!
8000 Lost Shaker Lane
Welcome to Margaritaville, a charming two-story residence with a front porch and lush garden.

8000 Lost Shaker Lane

3.0 star property
9.6 out of 10, Exceptional, (7)
"The house is absolutely beautiful. Very clean and has everything you need. Unfortunately you can’t use the pool which I didn’t understand so that was the only downside. The property is gorgeous. "
8000 Lost Shaker Lane
Tiny Hidden Cottage
Enjoy a meal with a view from this kitchen, featuring a large window and a potted plant.

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (48)
"Host provided eggs from chickens that roost on the property - nice extra!"
The price is CA $98
CA $198 total
includes taxes & fees
Aug 10 - Aug 11
Tiny Hidden Cottage
Family 4BR Home w/ Resort Pool Near Disney
House (4 Bedrooms) | Floor plan

Family 4BR Home w/ Resort Pool Near Disney

3.0 star property
Family 4BR Home w/ Resort Pool Near Disney
5003 Windermere Avenue
Relax by the pool with a meal at this outdoor dining area, featuring a table and chairs under a pendant light.

5003 Windermere Avenue

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location, convenient to all shopping needs. Close to Disney World. Good amenities. Great for families traveling together."
5003 Windermere Avenue
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Stroll through a serene garden with lush greenery, neatly trimmed hedges, and a variety of flowering plants.

Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,

8.4 out of 10, Very good, (15)
"This was a cute place in a nice neighborhood "
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Enjoy dining al fresco with a view of the surrounding buildings from this outdoor patio, featuring a table, chairs, and a sofa.

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

3.0 star property
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Gorgeous Cottage w/Private Pool + Balcony, Near Disney!
Overlooking a charming street lined with pastel-hued houses, this residence features a balcony with a white railing.

Gorgeous Cottage w/Private Pool + Balcony, Near Disney!

9.8 out of 10, Exceptional, (48)
"We had a great stay! Very clean, spacious for a family of 4, easy access to Disney parks, food/shopping. Will definitely stay again! "
Gorgeous Cottage w/Private Pool + Balcony, Near Disney!
Private Patio: College Park Cottage in Orlando!
Welcome to a serene single-story home surrounded by a lush lawn and a majestic tree.

Private Patio: College Park Cottage in Orlando!

10.0 out of 10, Exceptional, (8)
"I stayed here for a month with my dog. It was exactly what I needed! The hosts thought of everything that you could possibly need. There is a ton of space and everything is organized and clean. Location is great being close to local shops, necessities, and major roads."
Private Patio: College Park Cottage in Orlando!
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Fitness center entrance with a welcoming walkway and lush surroundings.

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

3.0 star property
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Modern Townhome W/private Pool & Free Water Park!
Residents can enjoy a central swimming pool complex surrounded by well-maintained lawns and pathways.

Modern Townhome W/private Pool & Free Water Park!

4.0 star property
8.8 out of 10, Excellent, (5)
"This property was excellent and lived up to the expectations in the post! So close to the parks, we came back everyday to cool down by the pool and recharge our batteries."
Modern Townhome W/private Pool & Free Water Park!
Dtwn Winter Garden Home: 12 Mi to Disney!
Cozy home with a covered porch and a beautiful tree-lined yard.

Dtwn Winter Garden Home: 12 Mi to Disney!

10.0 out of 10, Exceptional, (13)
"We had a wonderful stay in Analia’s home. It was a perfect location and 4 adults were quit comfortable for two weeks. "
Dtwn Winter Garden Home: 12 Mi to Disney!
Townhome Splash Pool BBQ Free Water Park!
Stunning two-story building with a central entrance, surrounded by lush greenery and a beautifully manicured lawn.

Townhome Splash Pool BBQ Free Water Park!

3.5 star property
9.6 out of 10, Exceptional, (10)
"Nice and relaxing quiet neighborhood "
Townhome Splash Pool BBQ Free Water Park!
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Guests can enjoy a peaceful stay at Woodside Motel, surrounded by lush greenery and a quiet residential area.

Gorgeous Cottage near Lake Louisa & mins 2 Disney.

9.6 out of 10, Exceptional, (50)
"Great little place, bring your quarters loved the candy machine. Was a awesome place to enjoy while we were there for a wedding. Some games in house would have been cool, but me and the wife enjoyed the stay, bring your own pillows fyi."
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Jedi cottage 4 miles from Disney! Mins from universal!
Enjoy a home away from home with a spacious porch and patio.

Jedi cottage 4 miles from Disney! Mins from universal!

9.4 out of 10, Exceptional, (21)
"We loved staying here! "
The price is CA $87
CA $274 total
includes taxes & fees
Aug 14 - Aug 15
Jedi cottage 4 miles from Disney! Mins from universal!
3148 Caribbean Soul Drive
Relax in style on the patio with two Adirondack chairs, surrounded by a beautifully landscaped garden.

3148 Caribbean Soul Drive

3.0 star property
3148 Caribbean Soul Drive
3050 Pirate Way
Ford's Garage features a charming garden and a single-story building with a flat roof.

3050 Pirate Way

3.0 star property
3050 Pirate Way
Lovely Spacious Guesthouse in Mills 50 District, Orlando
Enter a cozy retreat with a warm and inviting atmosphere, featuring a glass door, wooden fence, and string lights.

Lovely Spacious Guesthouse in Mills 50 District, Orlando

10.0 out of 10, Exceptional, (1)
"Loved this space, by great locations. Can’t wait to visit again."
Lovely Spacious Guesthouse in Mills 50 District, Orlando
3000 Latitude Lane
Relax by the pool surrounded by a beautifully maintained patio with seating.

3000 Latitude Lane

3.0 star property
9.6 out of 10, Exceptional, (4)
"Great stay!"
3000 Latitude Lane
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.
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Top Windermere Hotel Reviews

Hyatt Regency Orlando

Hyatt Regency Orlando

10/10 Excellent
"We loved every moment of it "
Emil 3-night trip
Posted 6 hours ago
Hyatt Regency Orlando