Search Winter Garden Cottage Rentals from CA $111

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Winter Garden Cottages

Orlando Lakefront Tiny House Community
The Club House

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (236)
"Amazing cozy community"
The price is CA $111
CA $230 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Orlando Lakefront Tiny House Community
Tiny Hidden Cottage
Fridge, microwave, stovetop, coffee/tea maker

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (24)
"The house was perfect for my weekend stay and I hope to stay again on my next trip"
The price is CA $113
CA $220 total
includes taxes & fees
Dec 29 - Dec 30
Tiny Hidden Cottage
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
2 bedrooms, in-room safe, desk, iron/ironing board

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

9.8 out of 10, Exceptional, (9)
"It's a lovely, well-appointed, well-located place. The cottage is within easy walking distance of multiple restaurants. The communication was excellent. I hope to stay at the cottage again soon!"
The price is CA $251
CA $499 total
includes taxes & fees
Jan 12 - Jan 13, 2025
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood
TV, books

High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood

10.0 out of 10, Exceptional, (121)
"Wonderful hosts and perfect location. We have returned many times and hope to visit again soon."
High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood
Orlando Holiday Special! Guest House with Private pool & WiFi
Property grounds

Orlando Holiday Special! Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (26)
"I had surgery and stayed here for my recovery, nice quiet area, easily accessible to stores and very comfortable bed. I felt very comfortable while recuperating. Washer and dryer big plus and the pool was beautiful and well kept. I didn't get to use the pool but I sure would have loved to. I will be back when I have to go for my checkups "
Orlando Holiday Special! Guest House with Private pool & WiFi
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Outdoor pool

Gorgeous Cottage near Lake Louisa & mins 2 Disney.

9.6 out of 10, Exceptional, (37)
"Glad to report place is as nice as depicted in photos. House is part of a duplex in a community of homes called Vacation Village Resort. Two true bedrooms and two true baths. I don't want to give away the surprise but have a couple of quarters handy especially if traveling with kids. Small but highly functional kitchen area with full size refrigerator and a dishwasher as well. "
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Historic Tremain Cottages
Front of property

Historic Tremain Cottages

3.0 star property
8.4 out of 10, Very good, (29)
"This is an excellent quaint property. It’s in a quiet area and is walkable to town. It’s wonderful."
The price is CA $314
CA $348 total
includes taxes & fees
Dec 26 - Dec 27
Historic Tremain Cottages
Enchanted Cottage with Pool and Mini-Golf Near Disney
Fridge, microwave, oven, stovetop

Enchanted Cottage with Pool and Mini-Golf Near Disney

9.6 out of 10, Exceptional, (14)
"This location was perfect for me and my two dogs. "
Enchanted Cottage with Pool and Mini-Golf Near Disney
Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL
Pool

Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL

10.0 out of 10, Exceptional, (16)
"Nice to be able to walk downtown to enjoy the Christmas activities and restaurants without having to find parking. Also close to the Christmas Parade. The home was very clean and had plenty of kitchen supplies. Highly recommend if staying in the area."
Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL
Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly
Lobby

Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly

10.0 out of 10, Exceptional, (3)
"SO nice that each couple had a queen or king sized bed and each bedroom had its own bathroom. Hot tub was a huge bonus after long days on your feet at the theme parks. Very nice house in a beautiful area convenient to the Disney parks."
Frankly Fintastic - Happy Days in Margaritaville! Min to Resorts, Pet Friendly
Up to Scale With Margaritas
Property grounds

Up to Scale With Margaritas

3.0 star property
8.8 out of 10, Excellent, (6)
"The only issue was the upstairs airconditioner was not working in terms the rooms were hot while hallway was cold. But nice for our family. "
Up to Scale With Margaritas
Cozy Cottage 3 blocks from town
Miscellaneous

Cozy Cottage 3 blocks from town

10.0 out of 10, Exceptional, (21)
"The cottage has everything you need. It has an excellent location and is clean and well maintained. Debbie, our hostess was wonderful - very attentive & accommodating. Highly recommend staying here. "
Cozy Cottage 3 blocks from town
Stunning Lakeview Townhome w/ Private Pool!
Outdoor pool

Stunning Lakeview Townhome w/ Private Pool!

4.0 star property
8.4 out of 10, Very good, (9)
"Perfect location house was just what is described "
Stunning Lakeview Townhome w/ Private Pool!
Cozy Lake Front Cottage
Property grounds

Cozy Lake Front Cottage

10.0 out of 10, Exceptional, (9)
"Will definitely be staying again"
The price is CA $257
CA $456 total
includes taxes & fees
Dec 27 - Dec 28
Cozy Lake Front Cottage
8000 Lost Shaker Lane
Interior

8000 Lost Shaker Lane

3.0 star property
9.6 out of 10, Exceptional, (5)
"Lots of room , beautifully decorated. Close to everything we needed for the weekend . "
8000 Lost Shaker Lane
Davenport Family Home ~ 10 Mi to Animal Kingdom
House (3 Bedrooms) | Interior

Davenport Family Home ~ 10 Mi to Animal Kingdom

3.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect two day stay for us … close to everything we n ended it to be. "
Davenport Family Home ~ 10 Mi to Animal Kingdom
Beautiful Historic Cottage, Nantucket, RIGHT DOWNTOWN. BIG DISCOUNTS THIS MONTH
Fridge, microwave, oven, dishwasher

Beautiful Historic Cottage, Nantucket, RIGHT DOWNTOWN. BIG DISCOUNTS THIS MONTH

9.8 out of 10, Exceptional, (6)
"My husband and I really love the place . The decor was so cute. We could walk downtown Mount Dora from where we were at we never had to get into our car. The host was very accommodating with everything will return if we come back to Mount Dora."
The price is CA $283
CA $347 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Beautiful Historic Cottage, Nantucket, RIGHT DOWNTOWN. BIG DISCOUNTS THIS MONTH
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Outdoor pool

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

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
Parkside Serenity by Avantstay Private Pool!
Interior

Parkside Serenity by Avantstay Private Pool!

3.0 star property
Parkside Serenity by Avantstay Private Pool!
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.
Don't see what you're looking for?
See all available properties in Winter Garden
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Winter Garden

Lake Buena Vista Resort Village & Spa
2 outdoor pools, a heated pool, open 8:00 AM to 10:00 PM, pool umbrellas

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very good, (8221)
"Appliances should be updated. Great room along with Great customer service! Would definitely use again!"
Lake Buena Vista Resort Village & Spa
The View Studio Suites and Event Venue
Property entrance

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very good, (646)
"The staff was friendly and eager to help guests with questions or requests. "
The price is CA $110
CA $124 total
includes taxes & fees
Jan 12 - Jan 13, 2025
The View Studio Suites and Event Venue
Floridays Resort Orlando
2 outdoor pools, a heated pool, open 7:00 AM to 11:00 PM, pool umbrellas

Floridays Resort Orlando

3.5 star property
8.6 out of 10, Excellent, (11123)
"The front staff was very friendly and informative. Cute little place near a ton of activities. Recommend "
The price is CA $270
CA $352 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Floridays Resort Orlando
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.

Frequently asked questions

How much do cottages in Winter Garden cost?
Prices for cottages in Winter Garden range between CA $111 and CA $314 per night. Whatever your budget, you’ll find the perfect place to get reacquainted with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Winter Garden with Expedia?
Reserving a cottage in Winter Garden is as easy as entering your travel dates and picking an ideal place for a vacation in the outdoors. From upmarket retreats to budget-friendly stays and cottages that include perks like a hot tub, Expedia has something for all tastes. As for irresistible deals? We’ve got you covered!
How can I find cheap cottages in Winter Garden?
Expedia can help you locate cheap cottages in Winter Garden. To book your dream stay in a few quick keystrokes, try out our handy filter tool to refine your search by star rating, budget and amenities.
What is there to do in Winter Garden near my cottage?
There are plenty of fantastic things to do in Winter Garden. Head for big attractions like Winter Garden Heritage Museum, Garden Theatre and Carter Family Bowl. Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail also lure many visitors.