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Check prices for these dates

Compare 36 Guest Houses in Winter Park with updated reviews, rates, and availability.

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 SAR 319
SAR 645 total
includes taxes & fees
27 Mar - 28 Mar
Downtown Lake Eola Historic House 1 OR 2 BED

SPRING LAKE GETAWAY SUITE (Detached Guest House)

10.0 out of 10, Exceptional, (63)
"great place. great host. Gina is very nice and helpful"
SPRING LAKE GETAWAY SUITE (Detached Guest House)

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

 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 

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!"
The price is SAR 698
SAR 1,487 total
includes taxes & fees
7 Apr - 8 Apr
Mills Cottage by the Little Lake

Downtown Orlando Throne Historic Thornton Park

10.0 out of 10, Exceptional, (3)
"Property is in a great location of Thornton Park. We arrived and parked the car. Walking distance to everything, such an awesome weekend."
The price is SAR 319
SAR 856 total
includes taxes & fees
17 Apr - 18 Apr
Downtown Orlando Throne Historic Thornton Park

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

9.2 out of 10, Wonderful, (15)
"This place was good for a two night pre cruise stay. Half of what you would pay staying at a hotel. A rental car is a must have for going anywhere. We just slept and showered here as we were out all day and brought takeout back. They provided a nice bottle of wine. I was disappointed that the bedding was not the nice white bedding pictured and was burgundy instead. A decent place to stay short term if you want to save on accommodations . "
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR

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 SAR 338
SAR 919 total
includes taxes & fees
7 Apr - 8 Apr
Beautiful Villa with Lake Views

Cozy Guesthouse in Orlando, Florida! Convenience and comfort!

9.6 out of 10, Exceptional, (4)
"Very convenient location. New fixtures. Very clean. "
Cozy Guesthouse in Orlando, Florida! Convenience and comfort!

Adorable 1bed 1 bath guest house

10.0 out of 10, Exceptional, (22)
"Our stay was perfect. The accommodations and hosts were excellent. Will definitely consider it again if/when coming to orlando. "
Adorable 1bed 1 bath guest house

Private studio; big outdoor space

10.0 out of 10, Exceptional, (20)
"We were very pleased with our hosts and their responsiveness to any concerns we had. The property worked very well for us as we spent our days with family and returned to our quiet place in the evenings. "
Private studio; big outdoor space

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

City Guesthouse in beautiful Historic Downtown Sanford

9.8 out of 10, Exceptional, (8)
"The unit was nice though the AC was not operating properly. The Hosts were very understanding and immediately offer/processed refund and assisted in instructing us on method of cancelation to get full refund from VRBO. VRBO was also extremely prompt in processing a our full refund. This was a first for us using VRBO and was very skeptical but after this experience I will not have any reservation about using VRBO again as well as booking through this host. The AC issues were out of the hosts...
City Guesthouse in beautiful Historic Downtown Sanford

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

Stunning Black and White 2 Bed APT

2.0 star property
Stunning Black and White 2 Bed APT

Casa Catalina☀️ Lakefront Apartment near Downtown

8.0 out of 10, Very Good, (1)
"So my girlfriends and I stayed for one quick night,which was perfect for one night because just a heads up the air conditioner is not cool in the living room. There is a air conditioner in the bedroom which gets really cool. The bed in the bedroom and the pullout sofa bed were both memory foam which were nice. The small apartment was cute and clean,very nice decor!"
Casa Catalina☀️ Lakefront Apartment near Downtown

Blissful Guest House

3.0 star property
2.0 out of 10, (1)
Blissful Guest House

2 Bed/2 Bath Villa @ Walt Disney's Grand Floridian Resort

2 Bed/2 Bath Villa @ Walt Disney's Grand Floridian Resort

Tree House

10.0 out of 10, Exceptional, (1)
"Erik at the beehive treehouse was the best host we’ve had in a while. He met us at the spot and showed us everything we needed to know and even bought flowers as a surprise because I told him it was my wife’s birthday. The treehouse is AMAZING, built with love and you feel it in every detail. Peaceful, serene, and quant. Couldn’t have asked for a better mini vacation spot. Thank you Erik!"
Tree House

Disney’s Top Villa Resort

Disney’s Top Villa Resort
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

4.0 star property
8.4 out of 10, Very Good, (8437)
"Love all about it,please work on the little thing .all was so good except when i went to leave it took me 7 trips to my vehicle to pack it.no one could find a luggage cart and no one really looked for one "
Lake Buena Vista Resort Village & Spa

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.2 out of 10, Wonderful, (1826)
"Nice hotel attached to a huge shopping mall with a Starbucks that opens at 6 am. Not sure what makes it a VIP Access hotel other than the free drink coupons. It’s an older hotel but kept up nicely and the staff are very friendly. "
The price is SAR 745
SAR 936 total
includes taxes & fees
21 Mar - 22 Mar
Florida Hotel & Conference Center in the Florida Mall

The View Studio Suites and Event Venue

3.0 star property
8.4 out of 10, Very Good, (948)
"All good"
The price is SAR 298
SAR 335 total
includes taxes & fees
1 Apr - 2 Apr
The View Studio Suites and Event Venue
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.