Search Winter Garden Cottage Rentals

  • 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

Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

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, (256)
"Great little, tiny home for a short stay in Orlando. The setting was divine. I wish it had been warmer -we were there during the polar vortex- so we could have enjoyed the lake and the amenities. Less than 30 minutes to Disney. Perfect for two people. Would stay again. "
The price is CA $104
CA $222 total
includes taxes & fees
Feb 23 - Feb 24
Orlando Lakefront Tiny House Community
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 $288
CA $538 total
includes taxes & fees
Feb 3 - Feb 4
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Tiny Hidden Cottage
Fridge, microwave, stovetop, coffee/tea maker

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (29)
"Cute tiny house. Very clean. Private. I was not happy with the AC window unit in the bedroom as it woke me up whenever it turned on. There is a chicken coop next to it with a rooster that greeted me in the morning. But I love backyard chickens so that was ok. Would be nice to provide ice for drinks and cream for coffee. Thanks. "
The price is CA $118
CA $226 total
includes taxes & fees
Feb 20 - Feb 21
Tiny Hidden Cottage
Cozy Cottage 3 blocks from town
Miscellaneous

Cozy Cottage 3 blocks from town

10.0 out of 10, Exceptional, (24)
"The Cozy Cottage is a short walking distance from town; took about 3-4 minutes! Quiet, clean and well appointed! The host/owner was very kind and attentive to making sure we had everything we needed for a pleasant stay. It was very comfortable. We thought it was perfect; just as described! "
Cozy Cottage 3 blocks from town
Large Villa W/private Pool & Game Room! Waterpark
Miscellaneous

Large Villa W/private Pool & Game Room! Waterpark

3.5 star property
9.6 out of 10, Exceptional, (10)
"Great property! Was perfect for our family and made down time from the parks really nice."
Large Villa W/private Pool & Game Room! Waterpark
Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome
Terrace/patio

Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome

2.0 star property
10.0 out of 10, Exceptional, (7)
"We highly enjoyed our stay, it was a pleasant 10min walk into downtown area. Home was very clean and beautifully designed. "
Charming 2-bedroom cottage in downtown Mount Dora with RV parking, pets welcome
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, (126)
"Spent the weekend, explored downtown great food. Visited the light house, took a tour. Relaxed, read just enjoyrd the down time."
High Hedges Cottage - Close to downtown Mt Dora in quiet neighborhood
Oasis At The Ruiz's - Come Relax, Have Fun, Or Enjoy The Arcade
Smart TV, video games

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

2.0 star property
10.0 out of 10, Exceptional, (6)
"Clean, cute perfect for the weekend for 2 couples. Maria is very responsive to any questions and very helpful. Will stay here again when in the area. "
Oasis At The Ruiz's - Come Relax, Have Fun, Or Enjoy The Arcade
SAVE 25 on any last minute booking. Celebrating 100 year birthday.
Miscellaneous

SAVE 25 on any last minute booking. Celebrating 100 year birthday.

10.0 out of 10, Exceptional, (50)
"We really enjoyed our stay here. The place was very clean, comfortable to hang out in, and well-stocked with all the essentials one might need for a few days getaway. Beds were comfortable, although new pillows were definitely needed on the two beds we used, so if possible, bring your own. The location was about .6 miles from the heart of everything, so once we parked, we never had to even move our car, which was excellent. The neighborhood itself was nice and quiet. Kimberly, the host, was...
SAVE 25 on any last minute booking. Celebrating 100 year birthday.
Florida Valentine’s Day Guest House with Private pool & WiFi
Property grounds

Florida Valentine’s Day Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (27)
"Very much enjoyed our stay. Weather didn’t allow pool use; but I’m sure it would have been great."
The price is CA $180
CA $385 total
includes taxes & fees
Mar 2 - Mar 3
Florida Valentine’s Day Guest House with Private pool & WiFi
Townhome W/private Pool & Themed Rooms, Near Wdw!
Miscellaneous

Townhome W/private Pool & Themed Rooms, Near Wdw!

4.0 star property
9.6 out of 10, Exceptional, (5)
"Great home and great resort! Loved having a private pool at the house and then all amenities included with the resort. Family had a great time. "
Townhome W/private Pool & Themed Rooms, Near Wdw!
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
Outdoor pool

Gorgeous Cottage near Lake Louisa & mins 2 Disney.

9.6 out of 10, Exceptional, (38)
"We enjoyed our stay at Vacation Village, and this Cottage. There are good instructions for most things. The cottage is stocked well with dishes & appliances. Refrigerator even had food for us to use - like condiments. That was nice, but we didn't expect that-it was confusing to us. Beds are very comfortable. It is very quiet there. A few things could be cleaned better: ovens, ceiling & other vents. TV is great in living room. Guest room TV didn't work - or remote didn't work. Blinds could be...
Gorgeous Cottage near Lake Louisa & mins 2 Disney.
"THE FISHERMAN'S COTTAGE" Historic District-Mount Dora's # 1 DESTINATION Rental!
Interior

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

10.0 out of 10, Exceptional, (100)
"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!
~ 10 Mi to Animal Kingdom: Davenport Family Home
House (3 Bedrooms) | Interior

~ 10 Mi to Animal Kingdom: Davenport Family Home

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. "
~ 10 Mi to Animal Kingdom: Davenport Family Home
The Beauclair * 3 min walk to Downtown Mt. Dora!!
Interior

The Beauclair * 3 min walk to Downtown Mt. Dora!!

10.0 out of 10, Exceptional, (45)
"Great location, very clean and thoughtfully stocked with lots of creature comforts. I’d definitely recommend this property and will be back. Thank you!"
The Beauclair * 3 min walk to Downtown Mt. Dora!!
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."
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
Parkside Serenity by Avantstay Private Pool!
Interior

Parkside Serenity by Avantstay Private Pool!

3.0 star property
Parkside Serenity by Avantstay Private Pool!
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
1-bedroom cottage just a 13-minute walk to Old Town
Outdoor pool, a heated pool

1-bedroom cottage just a 13-minute walk to Old Town

9.2 out of 10, Wonderful, (126)
"I will start by saying that this place is great. It is located in a gated RV/small home park with plenty of open spaces and amenities, near the Old Town area. It is economical and quite a bang for the buck. There were a couple of issues (the most notable one being a rather noisy washing machine, although Shawna said it was new and she'd look into it). It was a bit small for us, but the location was great, and we liked the large dog run for our doodles.I do have to say the neighborhood may...
1-bedroom cottage just a 13-minute walk to Old Town
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

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, (784)
"Spacious rooms, hotel is being renovated, close to restaurants and attractions "
The price is CA $117
CA $131 total
includes taxes & fees
Feb 5 - Feb 6
The View Studio Suites and Event Venue
Margaritaville Resort Orlando Cottages by Rentyl
Interior

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1179)
"The resort itself is wonderful. It is very convenient as there are many stores and restaurants at a walkable distance. However, we stayed at a Villa and it was not so clean. Floors did not look mopped prior to our arrival. Mattresses were also horrible and I didn't sleep well. When calling the front desk for anything they either took hours, days or the items were never delivered."
Margaritaville Resort Orlando Cottages by Rentyl
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, (8336)
"Loved it"
Lake Buena Vista Resort Village & Spa
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 and 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.