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Compare 71 Guest Houses in Winter Garden with updated reviews, rates, and availability.

Disney Proximity Escape - Comfort in Kissimmee
Room

Disney Proximity Escape - Comfort in Kissimmee

3.0 star property
8.0 out of 10, Very Good, (20)
"Was just a nice experience stayung there"
Disney Proximity Escape - Comfort in Kissimmee
The Heirloom Inn
Front of property

The Heirloom Inn

3.0 star property
8.8 out of 10, Excellent, (192)
"Great inn, right in the downtown, easy walking distance to everything! "
The price is SAR 422
SAR 657 total
includes taxes & fees
7 Jan - 8 January 2025
The Heirloom Inn
The Estate at Mount Dora
Exterior

The Estate at Mount Dora

3.5 star property
9.2 out of 10, Wonderful, (333)
"Beautiful old home "
The price is SAR 413
SAR 559 total
includes taxes & fees
6 Jan - 7 January 2025
The Estate at Mount Dora
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
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Detached Guesthouse over our 3 Car Garage

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (53)
"Very nice stay. Clean place and nice area. Hosts were very helpful and receptive. Will definitely stay again if I need to stay in that area!!"
SPRING LAKE GETAWAY SUITE (Detached Guest House)
Downtown Lake Eola Historic House 1 OR 2 BED
Living area

Downtown Lake Eola Historic House 1 OR 2 BED

8.8 out of 10, Excellent, (27)
"Very easy to find, historical home in a quiet neighborhood tucked between the ever growing city. A coffee shop around the corner, and right down the street is Lake Eola for a morning or evening stroll. A Publix grocery store just steps away. The home is very secure, with off street parking, comfortable bed, couch and air conditioning. Everything about our stay was just right. beautiful Lake Eola "
The price is SAR 287
SAR 610 total
includes taxes & fees
1 Jan - 2 January 2025
Downtown Lake Eola Historic House 1 OR 2 BED
Peaceful Room with 2 DBL Beds A Short Ride to Theme Parks
Property Entrance

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

9.6 out of 10, Exceptional, (7)
"My mother and I need some real rest so we decided to go to a different environment, which was Kissimmee. Beds were very comfortable, but a little too low!"
The price is SAR 199
SAR 304 total
includes taxes & fees
12 Jan - 13 January 2025
Peaceful Room with 2 DBL Beds A Short Ride to Theme Parks
Vibrant Room w 2 DBL Beds Near Local Attractions & Restaurants
Sun loungers

Vibrant Room w 2 DBL Beds Near Local Attractions & Restaurants

9.4 out of 10, Exceptional, (3)
"It was the best hotel for the price we stayed at. Great breakfast"
The price is SAR 199
SAR 304 total
includes taxes & fees
4 Jan - 5 January 2025
Vibrant Room w 2 DBL Beds Near Local Attractions & Restaurants
Mills Cottage by the Little Lake
Pool w/spa. 25/35 dollars a day additional to use pool/spa, pub/game room & gym

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
Spacious Park Royal Orlando Suite Near Theme Parks
Outdoor seating area

Spacious Park Royal Orlando Suite Near Theme Parks

7.8 out of 10, Good, (6)
"It was suite 2 rooms 2 queen beds one sofa bed easily accommodate family of six. 2 bathrooms. It’s spacious. The main disadvantage was the floor not clean. Need to have footwear. The AC was working good but little bit loud."
The price is SAR 267
SAR 381 total
includes taxes & fees
31 Jan - 1 February 2025
Spacious Park Royal Orlando Suite Near Theme Parks
Royal Park Orlando Peaceful Room with 2 DBL Beds and Pool
Living area

Royal Park Orlando Peaceful Room with 2 DBL Beds and Pool

9.6 out of 10, Exceptional, (13)
"This was so much better than what I had hoped for. Seasonal Pricing was super pool is awesome location exceptionally good "
The price is SAR 199
SAR 304 total
includes taxes & fees
4 Jan - 5 January 2025
Royal Park Orlando Peaceful Room with 2 DBL Beds and Pool
Tasteful Room with 2 DBL Beds Near Local-favorite Spots
Sun loungers

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 SAR 214
SAR 320 total
includes taxes & fees
6 Jan - 7 January 2025
Tasteful Room with 2 DBL Beds Near Local-favorite Spots
Kissimmee Family Vacation Room with 2 DBL Beds & Pool
Outdoor Furniture/Sun loungers/Swimming pool

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 SAR 199
SAR 304 total
includes taxes & fees
31 Jan - 1 February 2025
Kissimmee Family Vacation Room with 2 DBL Beds & Pool
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Room

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

9.8 out of 10, Exceptional, (13)
"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
Weekend Getaway Room w 2 DBL Beds in the Entertainment District
Living area/Dining area

Weekend Getaway Room w 2 DBL Beds in the Entertainment District

10.0 out of 10, Exceptional, (2)
"Definitely enjoyed my partner and I’d cute little getaway to Kissimmee. This property is by the parks and had everything we needed and more. Thank you!"
The price is SAR 199
SAR 304 total
includes taxes & fees
4 Jan - 5 January 2025
Weekend Getaway Room w 2 DBL Beds in the Entertainment District
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Private kitchen

 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 

10.0 out of 10, Exceptional, (77)
"Everything it was clean . The king bed is super comfortable. The host is communicative. The house it’s was surrounding the beautiful springs for hot summer. I recommend Mike cottage. "
 Peaceful Two Bedroom Guest House near Wekiva River and State Parks 
Spacious Room with 2 DBL Beds A Short Ride to Theme Parks
Outdoor seating area

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

The price is SAR 214
SAR 320 total
includes taxes & fees
4 Jan - 5 January 2025
Spacious Room with 2 DBL Beds A Short Ride to Theme Parks
Magnificent Room with 2 DBL Beds Close to Must-see Attractions
Outdoor Furniture/Sun loungers/Swimming pool

Magnificent Room with 2 DBL Beds Close to Must-see Attractions

9.6 out of 10, Exceptional, (15)
"Had a nice stay, clean property, only thing is the breakfast needs to be better if you’re charging for it"
The price is SAR 214
SAR 320 total
includes taxes & fees
5 Jan - 6 January 2025
Magnificent Room with 2 DBL Beds Close to Must-see Attractions
Spacious Suite in a Highly Desirable Location Near Theme Parks
Living room/Dining area

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 SAR 267
SAR 381 total
includes taxes & fees
5 Jan - 6 January 2025
Spacious Suite in a Highly Desirable Location Near Theme Parks
Tiny Cottage Farm House!
Living area

Tiny Cottage Farm House!

9.8 out of 10, Exceptional, (16)
"The tiny cottage was very well prepared and so cute. It is in a perfect area very quiet and calm. I would highly recommend for a small family for a mini vacation. "
Tiny Cottage Farm House!
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

The View Studio Suites and Event Venue
Front of property

The View Studio Suites and Event Venue

3.5 star property
8.4 out of 10, Very Good, (667)
"I loved how quiet the hotel was, and the lady at reception was so lovely! Cute room, and great breakfast options. Thanks so much for a lovely stay. "
The price is SAR 287
SAR 323 total
includes taxes & fees
22 Jan - 23 January 2025
The View Studio Suites and Event Venue
Lake Buena Vista Resort Village & Spa
Outdoor pool

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8228)
"Love very nice the place "
The price is SAR 686
SAR 883 total
includes taxes & fees
7 Jan - 8 January 2025
Lake Buena Vista Resort Village & Spa
Floridays Resort Orlando
Outdoor pool

Floridays Resort Orlando

3.5 star property
8.6 out of 10, Excellent, (11134)
"Good stay"
The price is SAR 639
SAR 846 total
includes taxes & fees
12 Jan - 13 January 2025
Floridays Resort 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.