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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

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

Orlando Lakefront Tiny House Community
The Club House | Individually decorated, individually furnished, laptop workspace

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (288)
"Rich was very helpful and available "
The price is AED 295
AED 600 total
includes taxes & fees
20 Apr - 21 Apr
Orlando Lakefront Tiny House Community
Florida Guest House with Private pool & WiFi
Outdoor pool

Florida Guest House with Private pool & WiFi

10.0 out of 10, Exceptional, (32)
"It’s a nice guest house, as described. I liked that it was a quiet area. "
Florida Guest House with Private pool & WiFi
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!

10.0 out of 10, Exceptional, (14)
"Easy and convenient in a nice place "
The price is AED 735
AED 1,365 total
includes taxes & fees
26 Apr - 27 Apr
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, (38)
"The cottage was cozy and complete, with even silverware and coffee cups. When the microwave stopped working, the owner went out and bought and set up a new microwave.She asked permission before showing up at the front door!"
The price is AED 290
AED 563 total
includes taxes & fees
27 Apr - 28 Apr
Tiny Hidden Cottage
Downtown Cottage
1 bedroom, desk, iron/ironing board, free WiFi

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 AED 367
AED 797 total
includes taxes & fees
21 Apr - 22 Apr
Downtown Cottage
3-br Condo BBQ & Heated Pool Near Disney&malls
Miscellaneous

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
Property grounds

Incredible Private Lakefront Cottage Retreat

10.0 out of 10, Exceptional, (26)
"One of our best stays. "
The price is AED 459
AED 1,175 total
includes taxes & fees
20 Apr - 21 Apr
Incredible Private Lakefront Cottage Retreat
Lakeview Home w/ Private Pool & Free Water Park!
Miscellaneous

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!
Property grounds

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
1 bedroom, desk, WiFi, bed sheets

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 AED 250
AED 760 total
includes taxes & fees
18 Apr - 19 Apr
The Sanford Foodie Guest House
Modern Townhome W/private Pool & Free Water Park!
Miscellaneous

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
Exterior

2BR COTTAGE IN SANFORD HISTORIC DISTRICT

10.0 out of 10, Exceptional, (98)
"This cottage is a quaint spot, inside and out. Cozy, clean and comfortable. Love the location. Great communication."
2BR COTTAGE IN SANFORD HISTORIC DISTRICT
5003 Windermere Avenue
Miscellaneous

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."
The price is AED 1,361
AED 2,685 total
includes taxes & fees
20 Apr - 21 Apr
5003 Windermere Avenue
Beautiful, Modern Home W/private Pool! Near WDW
Miscellaneous

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
Terrace/patio

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
Miscellaneous

4813 Crusoe Street

3.0 star property
4813 Crusoe Street
Luxurious Home W/private Pool, Near Disney!
Outdoor pool

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!
Outdoor pool

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!
Outdoor pool

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!
Exterior

Cozy Tiny Home Near Disney World & Orlando Parks!

8.0 out of 10, Very Good, (9)
"I really liked the location and the size of the cottage but people should not have to pay to stay with roaches, i dont live with them and i dont want to travel a 1000 miles to stay with them"
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
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, (8578)
"The pool was beautiful as well as the property! We will be going back 🌴"
The price is AED 493
AED 663 total
includes taxes & fees
22 Apr - 23 Apr
Lake Buena Vista Resort Village & Spa
The View Studio Suites and Event Venue
Exterior

The View Studio Suites and Event Venue

3.0 star property
8.4 out of 10, Very Good, (1021)
"5 stars "
The price is AED 267
AED 300 total
includes taxes & fees
20 Apr - 21 Apr
The View Studio Suites and Event Venue
Florida Hotel & Conference Center in the Florida Mall
Reception

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.0 out of 10, Wonderful, (1872)
"Good property"
The price is AED 639
AED 814 total
includes taxes & fees
26 Apr - 27 Apr
Florida Hotel & Conference Center in the Florida Mall
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.