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'Lakeside' in Olde Winter Park (in the exclusive 32789 zip code)

Bedrooms 4
Space 5,500 sq. ft.
Property type villa
Minimum Stay 4 - 5 nights


About the property

Lakeside Estate Home, 4 Bedrooms, 4 Baths, (Sleeps 8)

'Lakeside' is gracefully positioned on the shores of Lake Killarney in Winter Park and the highly sought 32789 zip code. Beautiful Lake Killarney is a favorite among the locals & guests in the know. Golden sunrises and spectacular sunsets reflect the pristine crystal clear lake in celebration of each day.

'Lakeside' was comfortably built for personal relaxation, renewal & entertaining. Our home is a genuine family estate home that is warm and inviting. Lakeside is also a desirable and memorable setting for gatherings & events, and several cinematic film locations.

'Lakeside' is an extraordinary location. Though you are only 'minutes from the city', our home is situated in the midst of an ecological sanctuary of rare birds & teeming aquatic life on the shores of a serene lakeside setting. Cruise by boat to the famed Hillstone's Restaurant , or Trader Joe's, both with dockside parking. Hop on I-4, and Disney World & Universal are just a 20 minute drive and Daytona Beach an easy 55 minutes.

However, everyone falls in love with the quaint town village of Winter Park and it's exclusive 'Park Avenue' (5 mins.). "The Ave." boasts of exceptional dining & shopping & galleries & museums and is fondly known to locals as 'little Europe'. And the highly acclaimed Rollins College is walking distance from the Ave..

The Winter Park zip code of 32789 is the highly sought residential address of celebrities, financiers, and professional athletes. Winter Park is well-known in Florida for its exclusive shopping, galleries & museums, and exquisite dining & eateries lined along the cobblestoned 'Park Ave' and tree-shaded Central Park. The Morse Museum, home to the world's largest collection of Louis Tiffany glass, is there. The 32789 area is the designation of 'Olde Winter Park'.

'Lakeside' is a 5,400 sq.ft. home reflecting the spirit of a New England coast shingle- style 4 bedroom, 4 bath family home. Constructed in 2009, the unique architectual design allows every living area to capture expansive views of the beautiful Lake Killarney.

The home's living areas are spacious, comfortably appointed, and adorned with wooden beams, coffered ceilings, and accented by an 18' stone fireplace. For the musically inclined, a Steinway grand piano. The oversized octagonal dining room is surrounded by glass with uninterrupted lake views. For your reading pleasure, Lakeside's cherry-wood library holds more than 700 titles. Integrated into the library's design is a home theatre system equipped with a 58" LED screen. The lakefront master suite is quiet and secluded with a master bath overlooking an atrium garden outside.

Lake Killarney (private access only) is a 300 acre spring-fed lake that serves as an eco-preserve/sanctuary for bald eagles, ospreys, great blue herons, and otters. Lake Killarney also enjoys a reputation for its bass fishing, water skiing, and paddleboarding. Lakeside has a large dock, a private beach, and more than 285 feet of lake frontage. Central Florida is well known as a golfer's mecca with more than 50 courses available year-round-- Lakeside is located only 4 minutes from the vintage City of Orlando 'Dubsdread Golf Club'.

Lakeside is located on the west end of Winter Park which provides very easy access to Interstate 4, the main transportation artery connecting you to Disney, Universal,and Sea World in minutes as well as 3 State Parks and 7 Florida coastal beaches within a 1 hour drive.

EVENTS and RECEPTIONS. There is an Event Fee and security deposit based on size of event. Please call Bonnie to discuss arrangements. 321.277.5301.


The lakeview master bedroom is furnished with a king pillow-top mattress, a full master bath which includes a large soaker bathtub, a separate shower, an enclosed toilet, and walk-in closet. Two other bedrooms are furnished with pillow-top queen beds; the 4th bedroom is furnished with two twin beds.

All bedrooms have their own full private baths connected to the bedrooms.


The spacious master bathroom has his & her dressing vanities, a large soaker bathtub overlooking an atrium garden area, a glass enclosed master shower, a privacy toilet room, and a walk-in closet.

All other bathrooms are privately adjoined to the bedrooms with a custom vanity and lavatory, a tub or walk-in shower, and toilet area.


Lakeside's design includes a whole-house audio system and additional iPod wall connections in each bedroom.

The lakefront has a small beach and a large dock equipped with a 21' Super Air Nautique excellent for wake boarding, water skiing, and tubing. [Because local regulations require a qualified boat driver, with advance notice we will arrange a boat driver for you for additional charge of $350/day.]

Fishing (bass) along the 285 ft shoreline is excellent. Basic fishing gear/tackle is available (though most guest prefer their own).

A regulation glass basketball goal is available for pick-up games at the side of Lakeside.



Private Transportation



Private Chef

Welcoming Personnel

EVENTS AND RECEPTIONS. We do charge an Event Fee and Security deposit based on size & nature of the event. Please call Bonnie to discuss arrangements - 321.277.5301.

Keywords: Home, Villa, Waterfront, Lake, luxury home, Walt Disney World, Orlando,Central Florida,Universal Studios,Sea World, beaches, attractions, exclusive, Park Ave., Rollins College, skiing, wake

boarding, paddle boarding, Disney, convenient, lakefront

More Details

Property Manager
Property Manager
Member since: 2010
Speaks: english
Response time:
Within a few days
Response rate:
Calendar last updated:
April 25, 2017

About The Owner

Our family has called beautiful Winter Park & Central Florida home for 29 years. Bonnie and John have 4 daughters and a son. Bonnie is a mother first, an educator and conference speaker; John is an attorney. Lakeside is the cherished home-place for their family. This home has become a personal entertaining venue for hosting friends and guests. Since John & Bonnie now travel & live a several months of the year out of state, they enjoy sharing their special home with others from around the world visiting the Central Florida community. This is a unique home that contains memories of a family that loves one another well, that enjoys life & fun, & shares those blessings with others.

The Owner purchased this villa in 2003

What makes this villa unique

Winter Park is a very special place. If you come to Central Florida and only visit the Theme Parks, you will have a good time... but also miss out one of the most beautiful villages in the State of Florida. Winter Park is a unique combination of a quiet, peaceful, brick-paved residential community, yet a bustling Park Avenue brimming with up-scale shopping, dining, parks, and museums. Disney is artificial fun--- Winter Park is authentic enjoyment. Winter Park is unlike any other place in don't want to miss it.


Northwest Orlando Villa Accommodation and Amenities

Property Type:
  • villa
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 5500 sq. ft.
House Rules:
  • Max. occupancy: 8
  • non smoking only
  • pets considered ...
  • Events Allowed
  • children welcome
Location Type:
  • Lake ...
  • Lakefront ...
  • Town ...
  • Water View ...
  • Family
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning
  • Alarm Clock
  • Basic Soaps
  • Ceiling Fans
  • Clothes Dryer
  • Computer Available
  • Filtered Water
  • Fireplace
  • Hair Dryer
  • Heating
  • Internet
  • Iron & Board
  • Laundry Soap
  • Linens Provided
  • Local Maps
  • Local Restaurant Guide
  • Macintosh Computer
  • Mobile Phone
  • Paper Towels
  • Parking Off Street
  • Security System
  • Shampoo
  • Toilet Paper
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Blender
  • Coffee Grinder
  • Coffee Maker
  • Cooking Utensils
  • Dishwasher
  • Freezer
  • Grill
  • Ice Maker
  • Kitchen
  • Kitchenette
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining Room
  • seating for 10 people
  • 4 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
    Bathroom 4 -
  • 3 bathrooms are large walk-ins. 1 bathroom has a tub & shower
  • 4 Bedrooms, Sleeps 8
  • King size beds (1) The spacious lakeview master bedroom is furnished with a king pillow-top mattress, a full master bath which includes a large soaker bathtub, a separate shower, an enclosed toilet, and walk-in closet. The soaker tub has a large window opening to a private outdoor atrium., Queen size Beds (2) The second & third bedrooms are furnished with pillow-top queen beds; all linens provided. Private bathroom attached., Twin or Single Beds (1) 4th bedroom is furnished with two twin beds. All linens are provided. All bedrooms have a full private bath connected to the bedroom.
  • Books
  • Books for Kids
  • CD Player
  • DVD Player
  • Games
  • Music Library
  • Piano
  • Ping Pong Table
  • Radio
  • Satellite / Cable ...
  • Stereo
  • Television
  • VCR
  • Barbecue
  • Beach Chairs
  • Beach Towels
  • Boat ...
  • Boat with Paddles
  • Deck / Patio ...
  • Golf ...
  • Kayak / Canoe ...
  • Lawn / Garden
  • Motorboat
  • Outdoor Grill
  • Patio
  • Tennis ...
  • Terrace
  • Unscreened Porch / Veranda
  • Walkway to Water
  • Water Sports Gear
  • Wood Deck
  • Long-term Renters Welcome
Onsite Services:
  • Private Chef
  • botanical garden
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • museums
  • playground
  • recreation center
  • restaurants
  • synagogues
  • theme parks
  • water parks
  • zoo
Leisure Activities:
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • outlet shopping
  • scenic drives
  • shopping
  • shuffleboard
  • sight seeing
  • sledding
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • basketball court
  • cycling
  • fishing
  • freshwater fishing
  • golf
  • golf privileges optional
  • jet skiing
  • pier fishing
  • sailing
  • surf fishing
  • surfing
  • swimming
  • tennis
  • water skiing
  • water tubing
  • wind-surfing
Excellent restaurants close by, Walk-In Closets, Steinway piano, Basketball Court, Dock, Large Open Gathering Space, Home Theater, Whole-house audio system , Board Games, Books/Library, Tennis courts, Beach Chairs, Flotation Devices, Water Craft (motorized with driver), Water sports, Fishing, Water Ski Equipment, Lounge Chairs, Beach Towels, Whole House Audio System, Gourmet Kitchen, Pillow-Top Mattresses, Large Soaker Bathtub, All Bedrooms Have Own Private Baths, Master his and her Dressing Vanities, Atrium Garden Area, Museums, Upscale shopping and dining.


Exceptional! 5/5 -
(13 traveler reviews)

'Lakeside' in Olde Winter Park (in the exclusive 32789 zip code)
average rating of 5.0 based on 13 reviews

Awesome home away from home

  • 5 of 5

House was the perfect choice. Comfy beds, house was clean, homeowner was a dream to work with. Will stay again!

  • Submitted: Nov 1, 2016
  • Stayed: Oct 2016
  • Source: VRBO, from HomeAway
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0 0

Beautiful home with all the amenities you'll need.

  • 5 of 5

We rented this home for a work retreat - this house was very well-suited for the occasion not only because of its size, but because each room has its own ensuite. The house is very well-decorated while being inviting and comfortable: there were lots of places - whether in the living area, library, or porch - where small groups could breakaway for conversation. This property provided the perfect environment to both work, reflect, and get to know each other (the superbly equipped kitchen with two dishwashers was perfect for us to cook up family-style dinners). The neighborhood is a short drive from the grocery store and the lovely Winter Park restaurants and shopping - this allowed folks to do their own thing and not feel stuck in the house. And as a Southerner with a love of porches to rock on, I have to say that this one provided a stunning view of the lake. The owners were very easy to work with, and their daughter gave us a very helpful orientation to the house when we arrived. Unless it is absolutely necessary for you to have daily housekeeping, this property is most definitely better in quality, atmosphere, and convenience than most hotels.

  • Submitted: Aug 14, 2015
  • Stayed: Jul 2015
  • Source: VRBO, from HomeAway
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2 0

Memories to last a life time. A fairytale come true.

  • 5 of 5

Our three children and three grand children stayed with us in this beautiful home for the week leading up to our son's wedding. The owners were very attentive and every detail was perfectly explained prior to our arrival.

We rented double kayaks and enjoyed the lake to its fullest. The grand kids had a great time.

The master bedroom is an oasis and my husband enjoyed the beautiful, relaxing library.

It was perfect that everyone had their own bathroom and the bedrooms have good separation.

The kitchen was well stocked and easy to prepare meals

We hired Arthur's Catering to come to the home for our outdoor rehearsal dinner on the lawn. Our guests enjoyed jazz music and cocktails on the boat dock prior to our dinner.

Many quests from Orlando said they had no idea this beautiful home was there!

The dinner was breathtakingly beautiful. We would highly recommend Arthur's and this lovely home! We had cafe lights, beautiful floral arrangements, music, and the best atmosphere imaginable. Complete with a rainbow over the lake! NO KIDDING.

There is no traffic and unless you live in the neighborhood you would not travel through that area.

We were minutes to grocery shopping and restaurants.

We are happy to give this home and owners the highest rating.

  • Submitted: Oct 10, 2014
  • Stayed: Sep 2014
  • Source: VRBO, from HomeAway
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1 1

Lovely Lake House!

  • 5 of 5

We rented this house for my daughters sweet sixteen birthday let me just say all the kids said they would rather go there than any amusement park. They had the time of their lives tubing. Our captian was awesome! The only time we left was to go Discovery Cove which was a short 20 min drive oh and Publix. The location is so perfect and so peacful! The front porch i could live on. We are looking for a date to go back stayed 5 days and we were not ready to leave. Owner's were very easy to deal with and had everything we needed there. Thank you so much

  • Submitted: Jul 25, 2012
  • Stayed: Jul 2012
  • Source: VRBO, from HomeAway
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1 0
Ft. Lauderdale, FL, USA

Beautiful, welcoming home

  • 5 of 5

This is a beautiful, inviting home. Upon our arrival, we were greeted by the owner, Bonnie, who welcomed us into her home and showed us around. She spoke proudly of the town (Winter Park) and recommended several restaurants. The home, like its owner, exuded warmth and offered every amenity. Though we didn't cook any meals, we did host an afternoon birthday party for a 1 year old relative. The house has a huge gathering area which was ideal for not only the party but our family, which enjoyed morning coffee and late night snacking and board games in the kitchen, dining, sitting area. We would definitely recommend this home and would like to return when in the Winter Park, Orlando area. We enjoyed eating at the restaurants in Winter Park and marveled at the Tiffany collection at the Morse Museum. The kids also visited Islands of Adventure. Thank you John and Bonnie for opening your home to travelers.

  • Submitted: May 28, 2012
  • Stayed: May 2012
  • Source: VRBO, from HomeAway
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0 0
Detroit, MI


  • 5 of 5

The house is refined, comfortable, elegant. Enormous slate-tiled front porch looks out over the sloped front lawn and peaceful lake. A cook's kitchen, but with so many tasty restaurants so near, I'm afraid we only made breakfasts. Winter Park has an adorable downtown walking area for shops, bars, and restaurants. A fabulous getaway from all the crazy congestion of the amusement parks and highways. The owners were so helpful, responsive, and welcoming. We loved our stay.

  • Submitted: May 1, 2012
  • Stayed: Feb 2012
  • Source: HomeAway
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Nearest Airport
12 Miles
Orlando International Airport (OIA)
Nearest Barpub
2 Miles
Winter Park
Nearest Golf
1.5 Miles
Dubsdread Golf Course
Nearest Train
3 Miles
Winter Park
Nearest Motorway
0.5 Miles
Interstate 4
Nearest Restaurant
1.2 Miles
Houston's/Hillstone, Del Frisco's, Park Plaza
Nearest Ski
25 Metres
Home is lakefront with skiing available
Nearest Beach
50 Miles
Daytona Beach, Cocoa Beach

Central Florida is well known as a golfer's mecca with more than 50 courses available year-round. Lakeside is located only 4 minutes from the vintage City of Orlando 'Dubsdread Golf Club'.

Lakeside is located on the west end of Winter Park which provides easy access to Interstate 4 ( the main transportation artery) connecting you to Disney, Universal,and Sea World( 25 mins), as well as 3 State Parks , and 7 Florida coastal beaches within a 1 hour drive.


Rates & Availability

Northwest Orlando Villa Rental Rates

Rental Basis:
per property
Manager accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
Spring Break
Mar 1 2017 - May 15 2017
5 night minimum stay
Notes: Rates are based on 6 guests; add $75 per night, per additional guest
My Standard Rate
4 night minimum stay

Additional information about rental rates

Property Damage Protection $59
Taxes (rate Includes) $0
Refundable damage deposit $300
Pet- talk to Owner $0
Boat Rental-talk w Owner $0
Event- talk to Owner $0
Cleaning charge $295

Before an Event will be accepted, guests must discuss the proposed event with the Owners. An appropriate event fee & a refundable event security deposit will be determined. 321.277.5301
Before a reservation with a Pet is accepted, guests must discuss and receive permission from the Owners. An appropriate pet fee and pet security deposit will be determined. 321.277.5301
*Though our home is large and we have 4 bedrooms with private adjoining bathrooms, we can comfortably sleep 8 adults in beds at full capacity. If guests anticipate more than 8 adults staying, please kindly discuss with the Owners. 321.277.5301

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.
Enter dates for accurate pricing

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