A two-story house with a balcony, surrounded by lush greenery and trees.

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winter Park cottages

Exterior detail

1. 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.
$159 nightly
The price is $176
Sep 14 - Sep 15
Total with taxes and fees
Downtown Cottage
Exterior

2. 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, (52 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
$291 nightly
The price is $323
Sep 28 - Sep 29
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Outdoor dining

3. Luxury Lakefront Cottage - Private Hot Tub -Stunning Sunset Views near UCF

Luxury Lakefront Cottage - Private Hot Tub -Stunning Sunset Views near UCF
Orlando
$200 nightly
The price is $223
Sep 17 - Sep 18
Total with taxes and fees
Luxury Lakefront Cottage - Private Hot Tub -Stunning Sunset Views near UCF
Property grounds

4. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
$181 nightly
The price is $201
Sep 14 - Sep 15
Total with taxes and fees
Romantic Lakefront Getaway with Balcony near Downtown Orlando
Exterior

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.
$212 nightly
The price is $234
Sep 14 - Sep 15
Total with taxes and fees
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Terrace/patio

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.
$201 nightly
The price is $222
Sep 14 - Sep 15
Total with taxes and fees
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Property grounds

7. Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
$209 nightly
The price is $232
Sep 14 - Sep 15
Total with taxes and fees
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Property grounds

8. 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)
$331 nightly
The price is $368
Sep 14 - Sep 15
Total with taxes and fees
Shore Steps Cottage - Walking Distance To The Town Of Windermere
House (2 Bedrooms) | Interior

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
$444 nightly
The price is $499
Sep 20 - Sep 21
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
Property grounds

10. Th20 - 3BR House With Resort Access Near Parks

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
$416 nightly
The price is $467
Sep 17 - Sep 18
Total with taxes and fees
Th20 - 3BR House With Resort Access Near Parks
Exterior

11. Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
$187 nightly
The price is $209
Sep 14 - Sep 15
Total with taxes and fees
Newly Remodeled Tiny Home 20 minutes from Disney!~
Exterior

12. 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
$736 nightly
The price is $836
Sep 20 - Sep 21
Total with taxes and fees
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Exterior

13. Th60 - 3BR House Near Disney With Pool Access

Th60 - 3BR House Near Disney With Pool Access
3.0 star property
Orlando
$411 nightly
The price is $462
Sep 24 - Sep 25
Total with taxes and fees
Th60 - 3BR House Near Disney With Pool Access
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 Park Hotel Reviews

Coco Key Hotel & Water Park Resort

Coco Key Hotel & Water Park Resort

8/10 Good
"Very convenience location, staff were very friendly and helpful. Pool area was clean. Well maintain. rooms were nice. but need a little update. The table inside the room is not convenient for small children and older adults. The chairs are too high like a bar stools. Food in the hotel was very over priced. Found the hotel ok .would I go again yes . You have McDonald’s cici pizza ,Dunkin’ Donuts, Denny’s ,IHOP two minutes from the hotel walking distance.my grandkids enjoyed it very much."
IRENA 2-night trip
Posted 1 hour ago
Coco Key Hotel & Water Park Resort

Find out more about Winter Park

Winter Park Cottages information

Number of reviews
139
Accommodation
374 Cottages
Lowest Price
$176
Highest Price
$836

Frequently asked questions

How much do cottages in Winter Park cost?
Cottages in Winter Park range between $176 and $836 per night. These stays offer a chance to touch base 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.
Why book your cottage in Winter Park with Expedia?
Expedia has some terrific cottages in Winter Park, so start packing for a memorable vacation close to nature. If you have a fixed budget, choose how much you'd like to spend and the preferred star rating of your property. Or, make use of our filters to search for cottages with a pool or a kitchen. We'll help you find the perfect fit whatever your plans or bank balance.
How can I find cheap cottages in Winter Park?
Expedia is here to help you easily track down cheap cottages in Winter Park. To discover your dream stay in a couple of quick clicks, simply use our handy filter tool to tailor your search results by amenities, star rating and budget.
What is there to do in Winter Park near my cottage?
There are tons of superb things to sink your teeth into in Winter Park. Discover well-known attractions like Winter Park Country Club, Crealde School of Art and Winter Park Village. Casa Feliz Historic Home Museum, Albin Polasek Museum and Sculpture Gardens and Kraft Azalea Gardens are other must-see's.

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