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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Compare 64 Guest Houses in Winter Garden with updated reviews, rates, and availability.

The Estate at Mount Dora
Exterior

The Estate at Mount Dora

3.5 star property
9.2 out of 10, Wonderful, (345)
"Lovrly"
The price is AED 400
AED 542 total
includes taxes & fees
1 Apr - 2 Apr
The Estate at Mount Dora
The Heirloom Inn
Front of property

The Heirloom Inn

3.0 star property
8.8 out of 10, Excellent, (201)
"If you are looking for a cozy place to stay in Mt. Dora the Heirloom Inn is perfect! We only had one night but since everything is walking distance we got to do so much in a short time. Fun shops and excellent restaurant right there! We loved it. Very kind and responsive property manager which was an added bonus. Hope to be back!"
The price is AED 413
AED 642 total
includes taxes & fees
6 Mar - 7 Mar
The Heirloom Inn
Disney Proximity Escape - Comfort in Kissimmee
Outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas, sun loungers

Disney Proximity Escape - Comfort in Kissimmee

3.0 star property
8.2 out of 10, Very Good, (27)
"The room was spacious as is the bathroom, very clean, mattress extremely comfortable, I would recommend putting on the "top bed sheet" and then the white bedspread which was pretty but a bit rough against skin. All areas were new, well kept and very nice. Negatiives: Parking is very stressful, there's a driveway with a 2 car garage and 7 parking spaces....you have to know who is leaving when, which is impossible if you don't know the other guests, you're always afraid of blocking or being...
Disney Proximity Escape - Comfort in Kissimmee
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Property grounds

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (61)
"Nice residential gated community. Excellent welcoming host!"
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Downtown Lake Eola Historic House 1 OR 2 BED
Miscellaneous

Downtown Lake Eola Historic House 1 OR 2 BED

8.8 out of 10, Excellent, (29)
"We had an amazing time staying at this property. Everything was clean and the communication with the owner was amazing!"
The price is AED 312
AED 631 total
includes taxes & fees
9 Mar - 10 Mar
Downtown Lake Eola Historic House 1 OR 2 BED
Winter Park Getaway
Terrace/patio

Winter Park Getaway

10.0 out of 10, Exceptional, (3)
"The host was very helpful and welcoming without being overbearing as some can be. The space was clean, cute, and well stocked."
Winter Park Getaway
Cozy Guesthouse in Orlando, Florida! Convenience and comfort!
Fridge, oven, stovetop, coffee/tea maker

Cozy Guesthouse in Orlando, Florida! Convenience and comfort!

9.6 out of 10, Exceptional, (4)
"Very convenient location. New fixtures. Very clean. "
The price is AED 510
AED 1,274 total
includes taxes & fees
6 Mar - 7 Mar
Cozy Guesthouse in Orlando, Florida! Convenience and comfort!
Mills Cottage by the Little Lake
Outdoor pool, a heated pool

Mills Cottage by the Little Lake

10.0 out of 10, Exceptional, (44)
"Upon arriving nice neighborhood drive was seemed small but on our last day with multiple cars on lot it was easy to get out. I was impressed by the whole property, but the vegetation was by far my favorite thing the pool was easy to find there was so many things to keep us occupied if we needed. Owner was quick to respond and even checked in with us. Would definitely stay again!"
Mills Cottage by the Little Lake
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Fridge, microwave, oven, stovetop

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

10.0 out of 10, Exceptional, (79)
"The house was clean and pretty and perfect!! It’s all updated. Beds were super comfy and warm (it was cold the weekend we stayed). We did have an issue with a couple of minor things but Mike came over instantly and fixed them immediately. He was very attentive and very friendly and I enjoyed talking with him! We stayed for a soccer tournament and it was super close to Seminole Soccer Complex. I would absolutely stay there again! "
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Smart TV, books

2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

9.2 out of 10, Wonderful, (15)
"One bedroom with comfortable foldout futon in small living room. Small fridge, microwave, kettle were ideal for my stay. "
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Kissimmee Family Vacation Room with 2 DBL Beds & Pool
Iron/ironing board, bed sheets, wheelchair access

Kissimmee Family Vacation Room with 2 DBL Beds & Pool

9.6 out of 10, Exceptional, (4)
"We enjoyed our recent stay, it was perfect for me, my husband, and our daughter. Our flight arrived late but the desk had someone available who checked us in quickly even though it was the middle of the night. Housekeeping came by every day to make our beds and give us fresh towels which was amazing! The property is pretty close to the Disney parks too. My only complaint is the cleanliness upon arrival. The cabinet doors were standing open, the floors weren’t clean, and the mirrors were dirty....
The price is AED 213
AED 317 total
includes taxes & fees
13 Mar - 14 Mar
Kissimmee Family Vacation Room with 2 DBL Beds & Pool
Beautiful Villa with Lake Views
Interior

Beautiful Villa with Lake Views

10.0 out of 10, Exceptional, (1)
"UN APPARTEMENT TRES BIEN MEUBLÉ ET BIEN ÉQUIPÉ. UN AGRABLE SÉJOUR."
The price is AED 448
AED 1,076 total
includes taxes & fees
5 Apr - 6 Apr
Beautiful Villa with Lake Views
Tasteful Room with 2 DBL Beds Near Local-favorite Spots
Iron/ironing board, WiFi, bed sheets, wheelchair access

Tasteful Room with 2 DBL Beds Near Local-favorite Spots

8.0 out of 10, Very Good, (16)
"The property is a sleeper. It’s a good value for the money definitely not high end but perfect for budget minded families and business outings. I stay here often "
The price is AED 213
AED 317 total
includes taxes & fees
3 Apr - 4 Apr
Tasteful Room with 2 DBL Beds Near Local-favorite Spots
Spacious Room with 2 DBL Beds A Short Ride to Theme Parks
Iron/ironing board, bed sheets, wheelchair access

Spacious Room with 2 DBL Beds A Short Ride to Theme Parks

The price is AED 213
AED 317 total
includes taxes & fees
3 Apr - 4 Apr
Spacious Room with 2 DBL Beds A Short Ride to Theme Parks
Kissimmee Modern Room with 2 DBL Beds & Tennis Court
Iron/ironing board, free internet, bed sheets, wheelchair access

Kissimmee Modern Room with 2 DBL Beds & Tennis Court

9.0 out of 10, Wonderful, (2)
"Hubby had a fishing tournament nearby the stay was nice check in went well there is pretty good places in area for food and drink that was close within walking distance"
The price is AED 213
AED 317 total
includes taxes & fees
3 Apr - 4 Apr
Kissimmee Modern Room with 2 DBL Beds & Tennis Court
Spacious Suite in a Highly Desirable Location Near Theme Parks
1 bedroom, iron/ironing board, WiFi, bed sheets

Spacious Suite in a Highly Desirable Location Near Theme Parks

8.6 out of 10, Excellent, (4)
"This use to be a hotel and seems to have seen better days but had been reconditioned. Some were in some aspects. Not a top line place but was clean and served our need."
The price is AED 261
AED 372 total
includes taxes & fees
3 Apr - 4 Apr
Spacious Suite in a Highly Desirable Location Near Theme Parks
Park Royal Orlando Suite Located in the Entertainment District
1 bedroom, iron/ironing board, WiFi, bed sheets

Park Royal Orlando Suite Located in the Entertainment District

8.8 out of 10, Excellent, (8)
"Very Clean,the only thing that wasn’t a plus, was that they didn’t have carts for the luggage"
The price is AED 283
AED 396 total
includes taxes & fees
3 Apr - 4 Apr
Park Royal Orlando Suite Located in the Entertainment District
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Full-size fridge, microwave, oven, stovetop

Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio

9.6 out of 10, Exceptional, (15)
"Walking distance to Vanguard."
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Stunning Black and White 2 Bed APT
2 bedrooms, desk, iron/ironing board, free WiFi

Stunning Black and White 2 Bed APT

2.0 star property
Stunning Black and White 2 Bed APT
Private Poolside Guest House In Winter Park/Orlando
A heated pool

Private Poolside Guest House In Winter Park/Orlando

8.0 out of 10, Very Good, (2)
"The property, the location and host are all top notch."
Private Poolside Guest House In Winter Park/Orlando
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 Garden

Vacation Village at Parkway
Aerial view

Vacation Village at Parkway

3.0 star property
8.4 out of 10, Very Good, (1651)
"Everything was perfect "
The price is AED 306
AED 403 total
includes taxes & fees
18 Mar - 19 Mar
Vacation Village at Parkway
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, (8400)
"Very convenient. Close to the parks. Good parking. Kids loved the pool. Friendly staff. "
Lake Buena Vista Resort Village & Spa
Margaritaville Resort Orlando Cottages by Rentyl
Interior

Margaritaville Resort Orlando Cottages by Rentyl

4.0 star property
8.8 out of 10, Excellent, (1234)
"We loved so much about the stay, the cottages were modern but comfortable and smartly decorated. There were all the essentials in the kitchen even a huge amazing blender. The buildings were very attractive and painted lovely colors. Beds were comfortable and bathrooms as well (could have been a little more upgraded, basic shower stalls). The entire unit was very spacious also. The pools were gorgeous with chairs available right in front. However there were a few things we didn't like. We were...
Margaritaville Resort Orlando Cottages by Rentyl
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.