A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winter Garden cottages

A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

1. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is NZ$903
includes taxes & fees
2 Oct - 3 Oct
Fire Pit & Yard: Updated Winter Garden Home!
A covered porch with wicker chairs and a ceiling fan.

2. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (43 reviews)
"Accommodations were comfortable, quaint space. Bed was very comfortable. Just beware the shower is very narrow and ceilings low. Not ideal for a taller or bigger person. Nice and close to the downtown area. Would stay here again."
United States
Betty
The price is NZ$318
includes taxes & fees
1 Oct - 2 Oct
Historic Tremain Cottages
A serene landscape with a pond, trees with Spanish moss, and a palm tree.

3. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
10.0 out of 10, Exceptional, (1 review)
The price is NZ$683
includes taxes & fees
1 Oct - 2 Oct
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A house with a red door, a front porch, and a pathway leading to the entrance.

4. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is NZ$319
includes taxes & fees
4 Oct - 5 Oct
Downtown Cottage
A single-story building with the number 297, a red door, and a bench outside.

5. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (66 reviews)
"The place was beautiful, cozy and so clean!!!! loved the pool and enjoyed spending my birthday there! will visit again soon!"
United States
Sara L.
The price is NZ$452
includes taxes & fees
3 Oct - 4 Oct
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

6. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (21 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is NZ$420
includes taxes & fees
1 Oct - 2 Oct
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

7. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (25 reviews)
"The setting was very nice and in a quiet area, but conveniently located to travel around Florida. Cottage was clean and very comfortable. Would definitely stay again."
United States
Brenda P.
The price is NZ$513
includes taxes & fees
1 Oct - 2 Oct
Cozy Lake Front Cottage
A well-lit garden area with a gravel pathway, decorative lights, and various plants.

8. Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Mount Dora
10.0 out of 10, Exceptional, (25 reviews)
"Great stay! Very welcoming home and very comfortable beds. Would rent again."
United States
Thomas K.
The price is NZ$454
includes taxes & fees
11 Oct - 12 Oct
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
A white building with large windows and a brick pathway leading to it.

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

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
10.0 out of 10, Exceptional, (54 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
The price is NZ$571
includes taxes & fees
12 Oct - 13 Oct
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

10. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is NZ$412
includes taxes & fees
13 Oct - 14 Oct
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A small, single-story house with a gabled roof and a front porch.

11. Mount Dora Cottages

Mount Dora Cottages
3.0 star property
Mount Dora
9.4 out of 10, Exceptional, (212 reviews)
"Perfect spot"
United States
PATRICIA
The price is NZ$418
includes taxes & fees
1 Oct - 2 Oct
Mount Dora Cottages
A single-story house with a front porch, a flag, and a small garden area.

12. Mount Dora Home: Private Pool, Spa & Tropical Bar!

Mount Dora Home: Private Pool, Spa & Tropical Bar!
3.0 star property
Mount Dora
6.0 out of 10, (1 review)
The price is NZ$601
includes taxes & fees
5 Oct - 6 Oct
Mount Dora Home: Private Pool, Spa & Tropical Bar!
An aerial view of a resort with multiple swimming pools, a dock, and a residential area with houses.

13. Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
The price is NZ$1,451
includes taxes & fees
5 Oct - 6 Oct
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
A hallway with a dining area, a black metal chair, and a sign reading "Rendezvous".

14. Beautiful Historic Cottage, Rendezvous

Beautiful Historic Cottage, Rendezvous
Mount Dora
9.4 out of 10, Exceptional, (17 reviews)
"This property is the perfect location for walking downtown shops and dining! "
United States
Julie
The price is NZ$444
includes taxes & fees
27 Oct - 28 Oct
Beautiful Historic Cottage, Rendezvous
A residential area with houses featuring sloped roofs and solar panels.

15. Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is NZ$477
includes taxes & fees
20 Oct - 21 Oct
Upstay: Bright Family-friendly Retreat With Patio
A covered porch with white wicker furniture and green cushions, large windows, and a ceiling fan.

16. Beautiful Historic Cottage, The Garden

Beautiful Historic Cottage, The Garden
Mount Dora
10.0 out of 10, Exceptional, (15 reviews)
"It was a perfect house for our short stay. Great location."
United States
Connie D.
The price is NZ$424
includes taxes & fees
4 Oct - 5 Oct
Beautiful Historic Cottage, The Garden
A small cabin with a porch and a garage, surrounded by trees and a clear sky.

17. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
6.8 out of 10, (3 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is NZ$294
includes taxes & fees
1 Oct - 2 Oct
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a black microwave.

18. Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (9 reviews)
"Proximity to theme parks, restaurants, and shopping"
United States
NOLI
The price is NZ$292
includes taxes & fees
1 Oct - 2 Oct
Tiny house close to Disney KISSIMMEE
A modern living room with a sofa, a large wall clock, and a mirror.

19. Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"
United States
Joyce R.
Family-Friendly Cottage Near Orlando’s Top Attractions
A mobile home with a paved driveway, a lawn, and a golf cart parked in front.

20. Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is NZ$338
includes taxes & fees
4 Oct - 5 Oct
Perfect Place for a Perfect Vacation
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 Winter Garden Hotel Reviews

Kompose Boutique Resort at Theme Parks

Kompose Boutique Resort at Theme Parks

10/10 Excellent
"Breakfast was mobbed but I guess that's a sign of good food. Great pool and lazy river. My 4 year old loved it!!"
Douglas 2-night trip
Posted 1 hour ago
Kompose Boutique Resort at Theme Parks

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
445
Accommodation
2643 Cottages
Lowest Price
NZ$292
Highest Price
NZ$1,451

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between NZ$292 and NZ$1,451 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. 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.
What is there to do in Winter Garden near my cottage?
Whatever you're into, Winter Garden has plenty of things to keep you on the go. Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail are on many travellers' agendas. Don't forget to explore Winter Garden Art Association, Winter Garden Heritage Museum and Oakland Nature Preserve either. With Expedia's Winter Garden hotel deals, you'll be able to see more renowned attractions like these with the cash you save.

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