Private Poolside Guest House In Winter Park/Orlando

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Photo gallery for Private Poolside Guest House In Winter Park/Orlando

A house with a stone pathway leading to a glass door, surrounded by lush greenery and a pergola.
A kitchen with white cabinets, a wooden staircase, and a dining area with a round table and chairs.
A bedroom with a bed, a nightstand, a dresser, and two windows.
A living room with a TV on a cabinet, a sofa, a coffee table, and a window with blinds.
A residential backyard with a swimming pool, a covered patio, and a two-story house.

Reviews

8.0 out of 10
Very good

Highlights

  • Enjoy the heated pool

    A rare find in this area - swim in comfort or have a relaxing dip.
  • Discover nearby landmarks

    Walk to Orlando Museum of Art

Popular amenities

  • Patio
  • Private pool
  • Dog-friendly
  • Barbecue grill
  • Air conditioning
  • Garage parking available
The current price is $141
$4,222 for 30 nights
All fees included
Sep 30 - Oct 30

Explore the area

View in a map
Winter Park, FL
  • Place, Lee Road Shopping Center
    ‪17 min walk‬
  • Place, Orlando Museum of Art
    ‪18 min walk‬
  • Place, Orlando Science Center
    ‪3 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪28 min drive‬

Where you'll sleep

1 bedroom (sleeps 4)

Bedroom 1

1 Queen Bed

1 bathroom

Bathroom 1

Bathtub or shower · Toilet · Shower only · Jetted bathtub

Spaces

Deck or patio
Kitchen
Dining area
The current price is $141
$4,222 for 30 nights
All fees included
Sep 30 - Oct 30

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About this property

Private Poolside Guest House In Winter Park/Orlando

Beautiful and comfortable two-story cottage/detached guest house, centrally-located within an historic neighborhood. Located in the heart of Winter Park – close to I-4 for easy access to the theme parks. Includes a private entrance, efficiency kitchen, and access to a beautiful resort-style heated pool and grill.

First story features a comfortable living room with a cozy couch and flat-screen TV (with a Roku, including Netflix, Hulu, and a variety of other apps), a dining table and an efficiency kitchen with a small fridge and a two-burner stove (equipped with all the essentials - pots, pans, glasses/mugs, plates/bowls, microwave and coffee maker).

Second story features a spacious bedroom, with direct entrance at the top of the wooden staircase. Bedroom includes a comfy queen-size bed, dresser and closet. A full bathroom is located right off the bedroom.

Includes central AC/heating with a nest thermostat for easy controlling, push-button light switches throughout, access to a washer and dryer in the garage, and access to the outdoor backyard, including the pool and summer kitchen/grill.

Access the guest home with a keypad/smart lock. For the utmost security, each guest receives a unique code that is only active through the period of the stay. You'll have access to the whole guest home, washer and dryer in the garage, and everything in the back yard (including the pool and summer kitchen).

All backyard/common areas are shared with the main house, which is rented separately. Landscape and pool are maintained weekly.
Our prices include all fees. No hidden fees.

House Rules

Check in after 3:00 PM

Minimum age to rent: 21

Check out before 11:00 AM

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Children

Children allowed: ages 0-17

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Events

No events allowed

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Pets

Pets allowed: dogs less than 50 lbs per pet (limit one pet total)

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Smoking

Smoking is not permitted

Important information

You need to know

Property # 1231568
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

Frequently asked questions

Does Private Poolside Guest House In Winter Park/Orlando have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Private Poolside Guest House In Winter Park/Orlando?

As of Sep 19, 2026, prices found for a 1-night stay for 2 adults at Private Poolside Guest House In Winter Park/Orlando on Sep 30, 2026 start from $141, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Private Poolside Guest House In Winter Park/Orlando pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 50 lbs per pet.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Private Poolside Guest House In Winter Park/Orlando?

Check-in begins at 3:00 PM.

What time is check-out at Private Poolside Guest House In Winter Park/Orlando?

Check-out is at 11:00 AM.

Where is Private Poolside Guest House In Winter Park/Orlando located?

Situated in Winter Park, this guesthouse is within 1 mi (2 km) of Advent Health, Lee Road Shopping Center, and AdventHealth Orlando. Orlando Museum of Art and Orlando Science Center are also within 1 mi (2 km). AdventHealth Station is 19 minutes by foot.

Private Poolside Guest House In Winter Park/Orlando Reviews

Reviews

8.0

Very Good

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 1 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 1 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous!

The property, the location and host are all top notch.
Stayed 28 nights in Mar 2024
Verified review

6/10 Okay

great little place in Winter Park

Well maintained. Nice and clean. Coffee machine with capsules (a big plus!). Served my purpose very well.
Stayed 1 night in Mar 2018

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