Search Guest Houses in Winter Park

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Compare 32 Guest Houses in Winter Park with updated reviews, rates, and availability.

SPRING LAKE GETAWAY SUITE (Detached Guest House)
10.0 out of 10, Exceptional, 44 reviews
"Excellent and very professional host, very clean place and safe area and lots of restaurants, close to shopping center (Altamonte Spring) and food court."
SPRING LAKE GETAWAY SUITE (Detached Guest House)
 Peaceful Three Bedroom Guest House near Wekiva River and State Parks 
10.0 out of 10, Exceptional, 72 reviews
"This guesthouse was really nice! I have never stayed at such a clean rental before. My dad and I came down to FL to visit my brother's family nearby. This place was central to all of the places we wanted to visit. We loved rolling up to the stop sign and seeing a beautiful black bear emerge from the woods. We enjoyed our morning coffee on the screened in porch while hearing lots of chirps and a rooster or two somewhere nearby. The beds were really comfortable as well. I slept really well the...
 Peaceful Three Bedroom Guest House near Wekiva River and State Parks 
Winter Park Getaway
10.0 out of 10, Exceptional, 3 reviews
"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
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Adorable 1bed 1 bath guest house
10.0 out of 10, Exceptional, 14 reviews
"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
Tiny Cottage Farm House!
9.8 out of 10, Exceptional, 15 reviews
"Not only was the tiny farmhouse great, it was Super Cute!! All the thoughtfulness put into everything including the funny signs all over made my trip very enjoyable! Tanya was very responsive and respectful of my privacy (she lives on the property) I felt very safe and comfortable. Would highly recommend her place. Thanks again Tanya for creating a wonderful space 🤗"
Tiny Cottage Farm House!
2 Minutes to Universal Studios Theme Parks - Central, Relaxing and Chic 1BR
9.8 out of 10, Exceptional, 11 reviews
"EASY! Convenient. Quiet nice neighborhood!"
The price is $69
$148 total
includes taxes & fees
Jun 9 - Jun 10
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
10.0 out of 10, Exceptional, 5 reviews
"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
Downtown Orlando Throne Historic Thornton Park
10.0 out of 10, Exceptional, 1 review
"Nice size property great location great host"
The price is $85
$230 total
includes taxes & fees
Jun 11 - Jun 12
Downtown Orlando Throne Historic Thornton Park
Mills Cottage by the Little Lake
10.0 out of 10, Exceptional, 43 reviews
"Clean, quiet and in a great area. Very unique property; an oasis just off the street! We walked, jogged and enjoyed the amenities. Dreaming of a revisit."
The price is $184
$398 total
includes taxes & fees
Jun 10 - Jun 11
Mills Cottage by the Little Lake
Tiny Cottage - 3 MI to Downtwn w/ Grill & Hammocks
10.0 out of 10, Exceptional, 3 reviews
"The property was fantastic. The bed and bedding was so comfortable. Zero complaints. Highly recommended. Great communication with the owners. "
The price is $57
$181 total
includes taxes & fees
Jun 12 - Jun 13
Tiny Cottage - 3 MI to Downtwn w/ Grill & Hammocks
City Guesthouse in beautiful Historic Downtown Sanford
9.6 out of 10, Exceptional, 4 reviews
"Perfect"
The price is $94
$239 total
includes taxes & fees
Jun 11 - Jun 12
City Guesthouse in beautiful Historic Downtown Sanford
Beautiful Villa with Lake Views
10.0 out of 10, Exceptional, 1 review
"UN APPARTEMENT TRES BIEN MEUBLÉ ET BIEN ÉQUIPÉ. UN AGRABLE SÉJOUR."
Beautiful Villa with Lake Views
Casa Catalina☀️ Lakefront Apartment near Downtown
8.0 out of 10, Very Good, 1 review
"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 $115
$336 total
includes taxes & fees
Jun 9 - Jun 10
Casa Catalina☀️ Lakefront Apartment near Downtown
Modern and Romantiv Villa
10.0 out of 10, Exceptional, 7 reviews
"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
9.6 out of 10, Exceptional, 14 reviews
"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
3.0 star property
2.0 out of 10, 1 review
Blissful Guest House
Tree House
10.0 out of 10, Exceptional, 1 review
"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
2 Bed/2 Bath Villa @ Walt Disney's Grand Floridian Resort
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
The price is $129
$273 total
includes taxes & fees
Jun 9 - Jun 10
Cozy 1BR apt-Pool/Tennis/Gym/Near attractions
Dr. Phillips House
3.0 star property
8.2 out of 10, Very Good, 13 reviews
"AWESOME LOCATION AND A GREAT PLACE TO STAY. THE ROOM WAS ABSOLUTELY AMAZING!! NO TURN DOWN OR TOWELS AFTER THE FIRST NIGHT STAY ALTHOUGH IT WAS AT THE BEGINNING OF CORONA."
Dr. Phillips House
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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.

Other property types in Winter Park

Avanti International Resort
3.0 star property
7.8 out of 10, Good, 2,171 reviews
"Everything good, excellent location."
The price is $84
$112 total
includes taxes & fees
Jun 30 - Jul 1
Avanti International Resort
Lake Buena Vista Resort Village & Spa
4.0 star property
8.4 out of 10, Very Good, 7,320 reviews
"Good place"
The price is $158
$204 total
includes taxes & fees
Jun 9 - Jun 10
Lake Buena Vista Resort Village & Spa
Hyatt Regency Orlando International Airport
4.0 star property
9.4 out of 10, Exceptional, 4,907 reviews
"Thanks, Hyatt!! The service provided was excellent and professional!! "
The price is $209
$235 total
includes taxes & fees
Jun 30 - Jul 1
Hyatt Regency Orlando International Airport
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.

Winter Park Guest Houses information

Number of reviews
253
Accommodation
32 Guest Houses
Lowest Price
$57
Highest Price
$184

Recent reviews of Winter Park hotels
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