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Check prices for these dates

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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Maitland 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 $105
CA $218 total
includes taxes & fees
Aug 10 - Aug 11
Orlando Lakefront Tiny House Community
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 8 - Aug 9
Tiny Hidden Cottage
Historic Tremain Cottages
Stroll through the charming front yard, surrounded by lush greenery and a white picket fence, to the inviting porch area.

Historic Tremain Cottages

3.0 star property
8.4 out of 10, Very good, (31)
"Great location!"
The price is CA $185
CA $206 total
includes taxes & fees
Aug 11 - Aug 12
Historic Tremain Cottages
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,
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!
"THE FISHERMAN'S COTTAGE" Historic District-Mount Dora's # 1 DESTINATION Rental!
Relax in this stylish living room with a comfortable sofa, coffee table, and side table, perfect for unwinding.

"THE FISHERMAN'S COTTAGE" Historic District-Mount Dora's # 1 DESTINATION Rental!

10.0 out of 10, Exceptional, (111)
"This was absolutely the most unique, creative and fun place we have ever stayed!"
"THE FISHERMAN'S COTTAGE" Historic District-Mount Dora's # 1 DESTINATION Rental!
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!
The Pink Door Cottage-Historic Sanford
Relax in this charming gazebo with a dining table and comfortable seating.

The Pink Door Cottage-Historic Sanford

9.8 out of 10, Exceptional, (17)
"Fully equipped with everything one could need whilst staying here."
The Pink Door Cottage-Historic Sanford
Labor Day Getaway!! Guest House with Private pool & WiFi
Welcome to a charming single-story home with a red door, surrounded by lush greenery and a wooden fence.

Labor Day Getaway!! Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (40)
"Wonderful stay. This is my second time here and love the accommodations and location. Very quiet. "
Labor Day Getaway!! Guest House with Private pool & WiFi
Oasis At The Ruiz's - Come Relax, Have Fun, Or Enjoy The Arcade
Stunning front yard with potted plants, a large rock, and a small fountain.

Oasis At The Ruiz's - Come Relax, Have Fun, Or Enjoy The Arcade

2.0 star property
10.0 out of 10, Exceptional, (13)
"Enjoyed our stay, slept very well! Beds were very comfortable! "
Oasis At The Ruiz's - Come Relax, Have Fun, Or Enjoy The Arcade
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
16 Mi to Disney: Cottage w/ Deck in Winter Garden
Two-bedroom house with a front porch and yard, perfect for a family getaway.

16 Mi to Disney: Cottage w/ Deck in Winter Garden

10.0 out of 10, Exceptional, (12)
"This place was amazing! The location is perfect and the house is sooo cute! Would stay again for sure!!"
16 Mi to Disney: Cottage w/ Deck in Winter Garden
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
Escape to a peaceful retreat with a charming single-story house featuring a quaint porch and a welcoming front yard with a small garden.

~ 12 Mi to Disney: Downtown Winter Garden Cottage!

9.8 out of 10, Exceptional, (43)
"We LOVE staying at Flamingo House. We are a repeat customer and will be back again soon. Suzie and is wonderful to work with and the house is everything we need!"
~ 12 Mi to Disney: Downtown Winter Garden Cottage!
“1933” Sleeps 6, King Beds, Spacious, 5 min walk to downtown Mt. Dora
Enjoy cooking in this well-equipped kitchen with a sink, toaster, and dishwasher.

“1933” Sleeps 6, King Beds, Spacious, 5 min walk to downtown Mt. Dora

9.6 out of 10, Exceptional, (10)
"Very nice—comfy and had everything we needed. Loved the decor!"
“1933” Sleeps 6, King Beds, Spacious, 5 min walk to downtown Mt. Dora
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Stroll up the pathway to the charming front door, featuring a glass panel, and enter a serene home surrounded by lush trees and a beautifully manicured lawn.

Orlando Home w/ Private Pool: 10 Mi to UCF Campus!

3.0 star property
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Comfortable 4BR Getaway: Wifi & Parking Included
Stunning home with a beautifully manicured lawn and a charming front porch.

Comfortable 4BR Getaway: Wifi & Parking Included

3.0 star property
Comfortable 4BR Getaway: Wifi & Parking Included
Downtown Cottage
Two single beds with matching headboards and footboards, a ceiling fan, and a large window with vertical blinds.

Downtown Cottage

9.6 out of 10, Exceptional, (4)
"Thank you for a wonderful stay. This gem of a guest house is in a perfect location in the Mills50 area of downtown Orlando. A perfectly cozy little home with comfortable beds and a welcoming environment. We look forward to staying again next time we are in Orlando!"
The price is CA $80
CA $234 total
includes taxes & fees
Aug 10 - Aug 11
Downtown Cottage
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Traditional home with a gabled roof and front porch, surrounded by lush gardens.

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

10.0 out of 10, Exceptional, (26)
"Easy and convenient in a nice place "
The price is CA $247
CA $486 total
includes taxes & fees
Aug 11 - Aug 12
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Orlando Golden Girls Retreat: Prime Location!
House (1 Bedroom) | Interior

Orlando Golden Girls Retreat: Prime Location!

3.0 star property
Orlando Golden Girls Retreat: Prime Location!
Resort Townhome: Perfect Orlando Vacation Spot!!
House (3 Bedrooms) | Property amenity

Resort Townhome: Perfect Orlando Vacation Spot!!

4.0 star property
8.0 out of 10, Very good, (1)
Resort Townhome: Perfect Orlando Vacation Spot!!
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 Maitland Hotel Reviews

Drury Plaza Hotel Orlando - Disney Springs Area

Drury Plaza Hotel Orlando - Disney Springs Area

10/10 Excellent
"The Drury is a 5***** Resort without the Resort fees. The staff was amazing and everyone was so friendly and spoke every time they saw us. We stayed 8 nights and they remember us and were happy we were still there. I am already planning next years trip! "
Michele 7-night trip
Posted 14 hours ago
Drury Plaza Hotel Orlando - Disney Springs Area