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Cottage vacation rentals in Windermere

Find and book unique cottages on Airbnb

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Popular amenities for Windermere cottage rentals

Cottage rentals with a hot tub

Cottage in Kissimmee
4.79 out of 5 average rating, 28 reviews

The Cozy Porch

BillRating, 5 stars1 week ago
Heydi's place was fantastic, perfectly located, quiet, comfortable, clean, and convenient. While only being minutes away from tons of things to do from parks, restaurants, and other experiences, once in this spot it was quiet calm and relaxing. Everything you could need from laundry, a peaceful enclosed porch and outdoor patio area along with some very nice amenities such as a pool, gym, library, and even hot tub, this spot is everything would need and want. Heydi took every proactive step to make things as easy as possible for guests from arrival to stay to checkout. This is an ideal gem for those wanting to enjoy the parks or be near the airport with minimal time wasted in traffic, perfectly situated near every where you'd want to be while still offering some peace and quiet before and after. Heydi made our stay so much more enjoyable thanks to her thoughtfulness and accommodating approach. Thank you for a wonderful stay
Cottage in Kissimmee
4.77 out of 5 average rating, 43 reviews

Disney Owl Cottage - Kissimmee, Florida

NoraRating, 5 stars4 months ago
A cozy stay if you’re looking for a place to relax and stay over night. Host was very responsive on any communication I needed. I would recommend this cottage :)
Top guest favorite
Cottage in Kissimmee
5 out of 5 average rating, 14 reviews

Kiwi Cottage at Margaritaville Resort, near Disney

ClareRating, 5 stars1 month ago
My husband and I stayed for 2 weeks at this lovely cottage. It was clean and very comfortable with plenty of space. We loved using the private hot tub in the cool mornings and private pool in the afternoon. Hedging on the fences provided nice privacy. We only used our rental car once to make one run to target for s few groceries ( many beginning supplies were provided). Otherwise, we enjoyed walking to many restaurants. The owners were very communicative during the whole process. Very relaxing time.
Cottage in Kissimmee
4.74 out of 5 average rating, 150 reviews

Sherwood Forest Vacation Home Near Disney

CarolRating, 5 stars3 days ago
This is a great location to stay. close by all the attractions. it isconly about an hour away from the Kennedy Space Center and Cocoa Beach.
Top guest favorite
Cottage in Kissimmee
4.96 out of 5 average rating, 52 reviews

Mickey's Hideaway Cottage - 5 miles from Disney

TierraRating, 5 stars2 weeks ago
Had a great stay. Host was very responsive and friendly. The place was clean and comfy. The only recommendation I can make is to add basic essentials such as salt and pepper to the kitchen. Otherwise everything was 10/10!
Cottage in Kissimmee
4.63 out of 5 average rating, 115 reviews

Charming lakeside hideaway! Near Disney

MatheusRating, 5 stars3 weeks ago
Perfect House! As for the photos, we felt at home! Thank you so much
Guest favorite
Cottage in Kissimmee
4.89 out of 5 average rating, 38 reviews

Sherwood - Disney Get'A'Way

KaitlynRating, 5 stars2 months ago
Great stay nice and clean has everything that you would need for a stay in the Disney area. And very safe area where the air bnb is located :)
Cottage in Kissimmee
4.75 out of 5 average rating, 137 reviews

Hidden Lake View Cottage 4 miles from Disney!

CelesteRating, 5 stars1 week ago
This place was the perfect quiet spot to return to after a long day at Disney! It was cozy and quiet, and that back porch is spectacular!

Pet-friendly cottage rentals

Cottage in Yalaha
4.83 out of 5 average rating, 76 reviews

3BR/2BA Charming 1920's Lakefront Estate + Hot Tub

JaclynRating, 5 stars1 month ago
My family was looking for a quiet weekend getaway and this lake house was the perfect place for us! The lake views from the living room were spectacular. The house was charming and comfortable. It had everything we needed and more! The peacocks roamed the yard throughout the day and were a pleasant sight to see. The dock was enjoyed by the whole family! We watched beautiful sunsets. My sons used the kayak. We fished for crappie and caught a few! We brought our small fishing boat and cruised around Lake Harris. We made our way to the famous Dora Canal. The boat launch is minutes away from the house. We walked to the delicious bakery a mile away for morning coffee and pastries. The host was so helpful and available to answer any questions we had. We enjoyed our stay at this charming and serene lake house!
Top guest favorite
Cottage in Davenport
4.99 out of 5 average rating, 93 reviews

Classic Cottage in country setting

MattRating, 5 stars2 days ago
We enjoyed our stay! We were grateful to be able to have our dog with us. The yard was huge and completely fenced. The house was super clean and decorated beautifully. Quiet neighborhood. Nice, private fire pit area! we enjoyed a fire at night. Carport was nice to park the car under too! Great experience ! Highly recommend.
Cottage in Davenport
4.86 out of 5 average rating, 7 reviews

Charming Cottage #1

RayRating, 5 stars7 months ago
The water can smell at times. Very peaceful RV resort. 35-45 minutes from Disney. Would stay again.
Cottage in Kissimmee
4.89 out of 5 average rating, 19 reviews

Mickey&Minie Honey moon cottage house10 min.Disney

NaquieshaRating, 5 stars3 weeks ago
Enjoyed stay Quiet neighborhood
Superhost
Cottage in Clermont
4.96 out of 5 average rating, 46 reviews

Lilac Loft- Lake, Pool, Pickle Ball, Disney, FUN!

JustinRating, 5 stars6 months ago
We did rent this place because in the description it does say it has a heated pool unfortunately we came at the end of October and the pool wasn’t heated yet so we wasn’t able to swim
Cottage in Tavares
4.94 out of 5 average rating, 32 reviews

Unique cottage with a heated pool on the canal

MikeRating, 5 stars3 weeks ago
Absolutely wonderful place to spend our spring break. My son loved the loft! The pool was amazing and bug free. Loved the canal, no speeding boats, great fishing and easy access to the lakes. The appliances are top notch and there were so many dishes and utensils. Also an awesome selection of spices just in case you forgot something at home. Definitely would like to stay again!!
Cottage in Davenport
4.67 out of 5 average rating, 39 reviews

Free parking Full house lake view and king Bed

JasmynnRating, 5 stars1 week ago
The house was very clean and the beds were comfortable. The location was very quiet! Highly recommend will definitely be back!
Cottage in College Park
4.71 out of 5 average rating, 17 reviews

The Hideaway At College Park

Michelle C.Rating, 5 stars4 months ago
Tom is a fantastic host. He was responsive to our needs and really went out of his way to help us with what may have been a serious problem following our stay. Tom’s home is a safe haven for pups that are used to exploring their yards. The yard is completely fenced in with a six foot high fence. This kept our two boxer boys safe within the yard. Tom is constantly doing things to improve on the property. His creativity shines through on this cozy bungalow.

Private cottage rentals

Cottage in Orlando
4.88 out of 5 average rating, 289 reviews

Beautiful (AS SEEN on TV) Near Downtown & Airport

EmmaleighRating, 5 stars1 month ago
We only stayed here for a night after a convert but the place was super cozy and spotless. Notes were posted throughout the house with instructions for different things which helped the quick stay be a lot more smooth. Highly recommend! Host was extremely helpful as well.
Cottage in Clermont
4.7 out of 5 average rating, 139 reviews

Gorgeous Cottage near Lake Louisa & mins 2 Disney.

LinaRating, 5 stars1 month ago
Wonderful experience in this little condo inside a quiet and safe resort village. Temitayo provided very clear instructions for everything, from check in to check out, what to do with the key pads, and even where to find the circuit breaker. That last one came in handy when we came home one night to a dark entryway because a circuit had tripped. Everything was cozy and comfortable for our stay. I recommended this place to my friends in Minneola for their out of town guests in the future.
Guest favorite
Cottage in Winter Park
4.94 out of 5 average rating, 396 reviews

Winter Park Pearl 6 min drive to historic Park Ave

BenjaminRating, 5 stars1 week ago
Matthew was a great host! Answered all questions we had about the area and let us know when we left something behind.
Cottage in Winter Garden
4.91 out of 5 average rating, 105 reviews

~ 12 Mi to Disney: Downtown Winter Garden Cottage!

KimRating, 5 stars1 month ago
The house was very cute, clean and was in a great location. We were only two blocks from the Main Street (Plant St). There was a cute backyard for us to enjoy as well.
Cottage in Kissimmee
4.73 out of 5 average rating, 290 reviews

Cute Sandcastle Cottage near Disney

RobynRating, 5 stars1 month ago
Great little spot for a visit to central Florida! The house is comfortable and has all things necessary for a comfortable stay.
Cottage in Kissimmee
4.82 out of 5 average rating, 98 reviews

Central Florida Tiny Home Retreat

CarlyRating, 5 stars5 days ago
Tracy was wonderful!!! so cheerful and helpful. her cottage was adorable, and was in a really great RV park. it had lots of friendly year round residents. lots of places to walk or ride a bike. pool area was clean and was in the pool for hours. the best part of the trip to Florida was just having a host that was pleasant and helpful . had zero issues while I was there. would highly recommend and will definitely stay there again. thanks Tracy!!!
Guest favorite
Cottage in Clermont
5 out of 5 average rating, 13 reviews

Citrus Blossom Cottage

RobRating, 5 stars2 weeks ago
We rented Nikolette's place for my parents during their visit to Clermont, and the entire experience was flawless. The cottage is beautiful and tasteful. The location is perfect. Pictures are as they look and amenities are as listed. Nikolette was flexible with the checkin, too, which for us was very helpful. It was an all around great experience. The Citrus Blossom Cottage will be our go-to spot for lodging family whenever they visit in the future.
Cottage in College Park
4.91 out of 5 average rating, 69 reviews

Cottage Retreat in the City

AshleyRating, 5 stars4 weeks ago
Connie’s place was the perfect spot for a getaway—the amount of food places and experiences is just the cherry on top at this point. Not only can you wake up peacefully, you can have your morning coffee out on the patio with some beautiful wind chimes and a pair of adorable pups! My boyfriend and I definitely would love to visit again, as Connie was such a kind and welcoming host, greeting us and saying goodbye too!

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