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Check prices for these dates

Compare 253 Cottages in Winter Park with updated reviews, rates, and availability.

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (292)
"Its a tiny house. The price was right."
The price is SAR 162
SAR 457 total
includes taxes & fees
30 Apr - 1 May
Orlando Lakefront Tiny House Community

Florida Guest House with Private pool & WiFi

10.0 out of 10, Exceptional, (34)
"Wonderful stay. This is my second time here and love the accommodations and location. Very quiet. "
Florida Guest House with Private pool & WiFi

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

10.0 out of 10, Exceptional, (15)
"Easy and convenient in a nice place "
The price is SAR 750
SAR 1,375 total
includes taxes & fees
28 Apr - 29 Apr
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (38)
"Host provided eggs from chickens that roost on the property - nice extra!"
The price is SAR 296
SAR 575 total
includes taxes & fees
28 Apr - 29 Apr
Tiny Hidden Cottage

Downtown Cottage

9.6 out of 10, Exceptional, (4)
"This place was alright. Clean & was exactly as described. Bare concrete floors are a bit of a drawback. "
The price is SAR 375
SAR 814 total
includes taxes & fees
5 May - 6 May
Downtown Cottage

3-br Condo BBQ & Heated Pool Near Disney&malls

3.0 star property
4.0 out of 10, (1)
"Mold on windows no screens on some windows. Faced a forest of trees no outdoor patio like I thought there would be. Communication was terrible the person I talked to on the phone knew nothing about the property never given times for the pools or that we could go to different pools within missed two days of swimming because of this showed a whirlpool tub but the spout for the tub didn’t even work "
3-br Condo BBQ & Heated Pool Near Disney&malls

Incredible Private Lakefront Cottage Retreat

10.0 out of 10, Exceptional, (26)
"One of our best stays. "
The price is SAR 518
SAR 1,159 total
includes taxes & fees
30 Apr - 1 May
Incredible Private Lakefront Cottage Retreat

Lakeview Home w/ Private Pool & Free Water Park!

3.5 star property
10.0 out of 10, Exceptional, (3)
"Love the inside heated swimming pool. Ive maker was not working."
Lakeview Home w/ Private Pool & Free Water Park!

Private Patio: College Park Cottage in Orlando!

10.0 out of 10, Exceptional, (8)
"We throughly enjoyed our stay! I would highly recommend staying at The Cottage!"
Private Patio: College Park Cottage in Orlando!

The Sanford Foodie Guest House

9.2 out of 10, Wonderful, (9)
"It was a great place to crash for a night. "
The price is SAR 281
SAR 806 total
includes taxes & fees
28 Apr - 29 Apr
The Sanford Foodie Guest House

Modern Townhome W/private Pool & Free Water Park!

4.0 star property
8.8 out of 10, Excellent, (5)
"This property was excellent and lived up to the expectations in the post! So close to the parks, we came back everyday to cool down by the pool and recharge our batteries."
Modern Townhome W/private Pool & Free Water Park!

2BR COTTAGE IN SANFORD HISTORIC DISTRICT

10.0 out of 10, Exceptional, (98)
"Wayne is an exceptional host always responsive and the property is spotlessly clean and very comfortable. We love our time in Sanford and look forward to returning next year Thank you Wayne for hosting us"
2BR COTTAGE IN SANFORD HISTORIC DISTRICT

5003 Windermere Avenue

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location, convenient to all shopping needs. Close to Disney World. Good amenities. Great for families traveling together."
5003 Windermere Avenue

Beautiful, Modern Home W/private Pool! Near WDW

4.0 star property
8.2 out of 10, Very Good, (13)
"It was a nice place ."
Beautiful, Modern Home W/private Pool! Near WDW

The Pink Door Cottage-Historic Sanford

10.0 out of 10, Exceptional, (13)
"This property was nice and met our needs very well. It is on a street that is decent, but the house backs up to a beautiful historic district with great areas to walk and explore. Felt very safe and enjoyed the area tremendously. "
The Pink Door Cottage-Historic Sanford

4813 Crusoe Street

3.0 star property
4813 Crusoe Street

Luxurious Home W/private Pool, Near Disney!

4.0 star property
8.0 out of 10, Very Good, (3)
"House was great, however chose to pay for the early check-in so we could use the pool. To use the heater for the pool it’s an up charge. Understand. However they charged me $25 per day for the entire stay but the pool wasn’t warm until the morning we checked out."
Luxurious Home W/private Pool, Near Disney!

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

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

Stunning Lakeview Townhome w/ Private Pool!

4.0 star property
8.8 out of 10, Excellent, (12)
"Great for kids and close to attractions!"
Stunning Lakeview Townhome w/ Private Pool!

Cozy Tiny Home Near Disney World & Orlando Parks!

8.2 out of 10, Very Good, (10)
"My husband and I stayed at this property while going to disney. Perfect size for us! Great property "
Cozy Tiny Home Near Disney World & Orlando Parks!
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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Other property types in Winter Park

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8625)
"Great lady at the check in very friendly and efficient. Great proximity to the park and kidos loved the pirate ship!"
The price is SAR 554
SAR 734 total
includes taxes & fees
28 Apr - 29 Apr
Lake Buena Vista Resort Village & Spa

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.0 out of 10, Wonderful, (1889)
"Beautiful property. The location was perfect for us. Love that the mall was right there so we had plenty of food options. Rooms were clean and the bed was comfortable."
The price is SAR 652
SAR 831 total
includes taxes & fees
10 May - 11 May
Florida Hotel & Conference Center in the Florida Mall

The View Studio Suites and Event Venue

3.0 star property
8.4 out of 10, Very Good, (1033)
"Amazing"
The price is SAR 257
SAR 290 total
includes taxes & fees
1 May - 2 May
The View Studio Suites and Event Venue
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.