Search Guest Houses in Winter Park

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Compare 33 Guest Houses in Winter Park with updated reviews, rates, and availability.

Winter Park Getaway
Property grounds
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, (47)
"Great place! We met the owner while there. Very nice and friendly. Everything was just as described and was great. Clean and well kept. (Loved that there was no carpet.) It was centrally located to everywhere we needed to go. Definitely would stay there again!"
SPRING LAKE GETAWAY SUITE (Detached Guest House)
 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 
Adorable 1bed 1 bath guest house
King bed, dresser, luggage rack, plenty of closet space with full mirror
Adorable 1bed 1 bath guest house
10.0 out of 10, Exceptional, (14)
"We were visiting our daughter in the area and stayed 5 nights. The home is very clean and very quiet. I loved that the main bedroom had blackout curtains and it was dark and comfortable to sleep in. We would definitely stay again!"
Adorable 1bed 1 bath 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, (26)
"The uniqueness of a historic home with a covered porch a block from the lake is incomparable!"
The price is SAR 281
SAR 603 total
includes taxes & fees
29 Sep - 30 Sep
Downtown Lake Eola Historic House 1 OR 2 BED
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, (12)
"The place was clean, organized, and included a bottle of wine which was so sweet! Host had great communication and instructions for arriving were super clear."
The price is SAR 281
SAR 599 total
includes taxes & fees
24 Sep - 25 Sep
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
Paradise in a country setting. 2 BDRM 1100 SQ FT apartment. 1 King ,1 Queen
Pool
Paradise in a country setting. 2 BDRM 1100 SQ FT apartment. 1 King ,1 Queen
10.0 out of 10, Exceptional, (6)
"Beautiful neighborhood, was perfectly centered for us to travel to a tigers game and cape Canaveral . There was a manned launch on one of the nights and we could see it from the deck. Friendly attentive owners, would definitely recommend."
Paradise in a country setting. 2 BDRM 1100 SQ FT apartment. 1 King ,1 Queen
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!"
The price is SAR 698
SAR 1,492 total
includes taxes & fees
24 Sep - 25 Sep
Mills Cottage by the Little Lake
Tiny Cottage - 3 MI to Downtown w/Grill & Hammocks
Tiny Cottage - 3 MI to Downtown w/Grill & Hammocks
8.6 out of 10, Excellent, (4)
"The property was fantastic. The bed and bedding was so comfortable. Zero complaints. Highly recommended. Great communication with the owners. "
The price is SAR 240
SAR 641 total
includes taxes & fees
29 Sep - 30 Sep
Tiny Cottage - 3 MI to Downtown w/Grill & Hammocks
Luxury Comfortable Guest Suite in Altamonte Springs - Large Pool
Pool
Luxury Comfortable Guest Suite in Altamonte Springs - Large Pool
Luxury Comfortable Guest Suite in Altamonte Springs - Large Pool
City Guesthouse in beautiful Historic Downtown Sanford
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
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."
Beautiful Villa with Lake Views
Casa Catalina☀️ Lakefront Apartment near Downtown
Living area
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!"
The price is SAR 432
SAR 1,246 total
includes taxes & fees
24 Sep - 25 Sep
Casa Catalina☀️ Lakefront Apartment near Downtown
Modern and Romantiv Villa
Interior
Modern and Romantiv Villa
10.0 out of 10, Exceptional, (7)
"You can stop looking…this one is perfect! Very clean, quiet, private outdoor sitting area, well equipped, beautiful, modern accommodations!"
Modern and Romantiv Villa
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Exterior
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
9.6 out of 10, Exceptional, (14)
"We had a wonderful stay! Cheryl and Eric were beyond kind and welcoming upon our arrival and showed us all around the guesthouse. They were very helpful and very quick to respond via messaging, but not intrusive at all, as we never saw them during our stay. The guesthouse was fun and ecclectic and a wonderful space. We were in town for th Olympic Marathon Trials so we parked the car and then were on foot throughout the weekend. Its such an amazing location to be able to walk everywhere! Quiet...
Quiet Garden Retreat Downtown Orlando - Private Apartment, Shared Pool and Patio
Blissful Guest House
Exterior
Blissful Guest House
3.0 star property
2.0 out of 10, (1)
Blissful Guest House
Cozy Guesthouse in Orlando, Florida! Convenience and comfort!
Living area
Cozy Guesthouse in Orlando, Florida! Convenience and comfort!
The price is SAR 315
SAR 1,096 total
includes taxes & fees
24 Sep - 25 Sep
Cozy Guesthouse in Orlando, Florida! Convenience and comfort!
Tree House
Property grounds
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
2 Bed/2 Bath Villa @ Walt Disney's Grand Floridian Resort
Room
2 Bed/2 Bath Villa @ Walt Disney's Grand Floridian Resort
2 Bed/2 Bath Villa @ Walt Disney's Grand Floridian Resort
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Interior
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Don't see what you're looking for?
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.
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Other property types in Winter Park

Hyatt Regency Orlando International Airport
Rooftop pool
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, (5380)
"Right in the airport and very clean"
The price is SAR 709
SAR 798 total
includes taxes & fees
24 Sep - 25 Sep
Hyatt Regency Orlando International Airport
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, (7961)
"Overall a great property highly recommended for some families or large groups"
The price is SAR 557
SAR 710 total
includes taxes & fees
24 Sep - 25 Sep
Lake Buena Vista Resort Village & Spa
Avanti International Resort
Pool
Avanti International Resort
3.0 star property
7.8 out of 10, Good, (2651)
"Stayed there 2 nights, no problems at all. They greeted me with smiles on their faces. The room was cute & definitely served its purpose. It’s almost right near icon park, just a short walk. The convenience was awesome. I wish the beds would have been a little more firm to my liking for my back, but I made due. Overall, it’s some place I would stay at again. "
The price is SAR 284
SAR 375 total
includes taxes & fees
30 Sep - 1 Oct
Avanti International 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.