Search Winter Park Cottage Rentals from CA $105

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Browse Select Winter Park Cottages

The Club House
Orlando Lakefront Tiny House Community
4.5 star property
9.2 out of 10, Wonderful, (140)
"One of the nicest places I stayed. Definitely will be back. Nice view and kayaking was fun, my boyfriend evens caught to fish. "
The price is CA $105
CA $218 total
includes taxes & fees
Jun 4 - Jun 5
Orlando Lakefront Tiny House Community
Outdoor pool
Stunning Lakeview Townhome w/ Private Pool!
4.0 star property
8.0 out of 10, Very good, (8)
"Perfect location house was just what is described "
Stunning Lakeview Townhome w/ Private Pool!
Private kitchen
Cottage II
9.2 out of 10, Wonderful, (17)
"It was a bit tricky to find as it is on a side road not the actual address of the main house but mission accomplished-I found it. I was happy to off the busy main road. I found everything easily and enjoyed my stay. I never saw the host or had any communication other than via email thru VRBO. I would recommend this as it was very well appointed and clean."
The price is CA $134
CA $239 total
includes taxes & fees
May 26 - May 27
Cottage II
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Exterior
Downtown Winter Garden Cottage ~ 12 Mi to Disney!
9.8 out of 10, Exceptional, (39)
"Very comfortable beds. Kitchen well equipped. Nice front porch to sit on. Walking distance to shops & restaurants in downtown Winter Garden. Would definitely recommend."
Downtown Winter Garden Cottage ~ 12 Mi to Disney!
Miscellaneous
Beautiful, Modern Home W/private Pool! Near WDW
4.0 star property
9.6 out of 10, Exceptional, (7)
"Well appointed but some amenities are damaged, needs to have overhaul to repair some areas zz"
Beautiful, Modern Home W/private Pool! Near WDW
Fridge, microwave, stovetop, dishwasher
Downtown Winter Garden Home ~ 12 Mi to Disney!
10.0 out of 10, Exceptional, (3)
"Very clean and nice. One thing I would have liked is a reading lamp."
Downtown Winter Garden Home ~ 12 Mi to Disney!
Property grounds
Quiet 1 bedroom Guest House with pool & WiFi Lake May, Florida
9.8 out of 10, Exceptional, (17)
"Beautiful and safe place to stay with your kids and family. Susy was always very cooperative with everything we needed."
The price is CA $163
CA $370 total
includes taxes & fees
May 30 - May 31
Quiet 1 bedroom Guest House with pool & WiFi Lake May, Florida
Miscellaneous
4214 Paragraph Drive
3.0 star property
4214 Paragraph Drive
Interior
Idyllic Sorrento Vacation Home w/ Patio & Grill
3.0 star property
10.0 out of 10, Exceptional, (1)
Idyllic Sorrento Vacation Home w/ Patio & Grill
Interior
Orlando Home w/ Lake View, Pool & Game Room!
3.0 star property
Orlando Home w/ Lake View, Pool & Game Room!
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!
Fridge, microwave, oven, stovetop
Cozy 3 BR/2 BA Downtown Winter Garden Cottage property.
The price is CA $137
CA $346 total
includes taxes & fees
Jun 10 - Jun 11
Cozy 3 BR/2 BA Downtown Winter Garden Cottage property.
Fridge, microwave, oven, stovetop
Lake View! Experience the Sunsets Here!
Lake View! Experience the Sunsets Here!
Interior
A curated stay in the Historic College Quarter
10.0 out of 10, Exceptional, (37)
"We stayed 4 nights. Hosts responded quickly and were so friendly. We walked daily around the neighborhood, along the lake trails, and through Rollins College. We could have walked to lots of shopping and lots of restaurants if it wasn’t Florida hot and we’d melt! It’s about 30 minutes to the Disney parks and the local museums are very close. Loved the house and would stay again."
A curated stay in the Historic College Quarter
In-room safe, desk, iron/ironing board, travel crib
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
10.0 out of 10, Exceptional, (2)
"This place was pretty amazing. The host left us just about anything we might need. No need to go to the grocery store. Also, lots of space. There's a private patio with tables and a grill if you want to hang out in the sun. The place is super nice and clean. It is right near I-4 in a good area. You can easily get to wherever you need to go quickly. 2 minutes and you are on the interstate. The hosts were responsive and there were no issues. I would definitely stay here again."
The price is CA $189
CA $410 total
includes taxes & fees
Jun 5 - Jun 6
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Fridge, microwave, oven, stovetop
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!
Fridge, microwave, stovetop, dishwasher
Modern Winter Garden Cottage: 16 Mi to Disney
9.8 out of 10, Exceptional, (8)
"Had a couple of reasons to contact manager. He was not as responsive as I would have liked. I also was not pleased with the final pricing. Otherwise location is good and convenient."
Modern Winter Garden Cottage: 16 Mi to Disney
Exterior
Cottage Retreat in the City
10.0 out of 10, Exceptional, (27)
"Very clean and inviting. Private. Lovely place."
Cottage Retreat in the City
Fridge, microwave, stovetop, cookware/dishes/utensils
The Tiny House Cottage @ Downtown Sanford
7.0 out of 10, Good, (2)
"Nice place still needs finishing up the building. 1. closet no flooring bare concrete. 2 . Rusty shower rods and tub spout falling off. 3. microwave was very small portable unit. 4. No nightlights inside 5. Pillows would flatten down to fast needs to be upgraded"
The Tiny House Cottage @ Downtown Sanford
Miscellaneous
Resort Townhome: Perfect Orlando Vacation Spot!!
4.0 star property
Resort Townhome: Perfect Orlando Vacation Spot!!
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See all available properties in Winter Park
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.

Other property types in Winter Park

Meeting facility
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, (4844)
"Very convenient "
The price is CA $259
CA $292 total
includes taxes & fees
May 29 - May 30
Hyatt Regency Orlando International Airport
Outdoor pool, pool umbrellas, sun loungers
Avanti International Resort
3.0 star property
7.8 out of 10, Good, (2090)
"Always stay at Avanti …Great time "
The price is CA $101
CA $137 total
includes taxes & fees
Jun 13 - Jun 14
Avanti International Resort
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, (7222)
"Nice location. Spacious. "
The price is CA $207
CA $269 total
includes taxes & fees
May 26 - May 27
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.

Winter Park Cottages information

Number of reviews
287
Accommodation
187 Cottages
Lowest Price
CA $105
Highest Price
CA $189

Recent Reviews in Winter Park
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