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Vacation Rentals & Homes in Winter Park Florida

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Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Winter Park, Florida.

Vacation Rentals - Winter Park Condo

Amazing location- walk to everything

Entire Private Home - 2 bed 2 bath fully furnished unit located just one block from Park Ave in Winter Park. ***Several units are available in the same building so please inquire for accurate availability***.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 5 Condo Rentals

Vacation Home

Apt E - Winter Park Apartment

Cozy Comfort In The Heart of Winter Park!

Modern, clean and unique. Bamboo wood floors, quartz counter tops, high-end cabinetry and fixtures, great new furnishings and mattresses, solid core interior doors, high ceilings, spacious open layout with a back door that opens right out onto the pool area and more! This property gets high ratings for very good reasons; come see! If you haven't explored Winter Park's Park Avenue, then you must! Salt water heated pool and hot tub. 1 reserved p.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Apartment Rentals

Vacation Home

Charming Winter Park Cottage - Winter Park Cottage

Mid Century Modern Cottage in The Heart of Winter Park

Furnished Mid Century Modern Short/Long term rental located in charming Olde Winter Park. Two bedrooms and one and half baths. Steps from shopping and restaurants and less than a mile from Park Ave with it's famous museums, parks, shops and dining. This home is complete with authentic mid century modern furnishings, new bedding, newly upholstered couches and chairs, new linens, two televisions (includes cable tv), central heat and air, new landsc.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 5 Cottage Rentals

Vacation Home

Vacation Rentals - Winter Park Guest house

Winter Park Bamboo Loft

Welcome to the Bamboo Loft! This beautiful property is 1 of 2 houses on a large lot. It has been newly renovated, with new beds, appliances, and a lot of personality! This cute cozy space offers tranquility from the moment you walk by the Bamboo forest. This 1/1 offers a queen bed in the private room and one day bed that offers two twin beds in the common area. Sleeps four people with no problem. Enjoy the patio area with friends and family on.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Guest house Rentals

Vacation Home

Winter Park Charm - Winter Park House

Winter Park charm. Close to Park Ave

Private 2 bedroom guest suite with its own entry and a separate sitting room. Tandem bedroom include 1 queen sized bed and bunk beds. Easily sleeping 4. We are located very close to downtown Winter Park and steps off Park Ave. Museums, restaurants, golf and shopping are all within walking distance. There is a dedicated desk/work area for corporate guest. Designed to feel like home away from home we want to make sure your stay with us is enjoya.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 House Rentals

Vacation Home

Vacation Rentals - Winter Park House

WeLive Winter Park / Spacious Enclave W/ Patio!

Welcome to WeLive Winter Park!! Incredible Oasis in the heart in winter park. Spacious cozy , loft style , sunlight, vanities full length body mirror and a fully stocked kitchen stoked with everything you need. THIS PROPERTY IS ONE OF TWO PROPERTIES ON THIS LOT. The house is 1800 square feet of comfortable space for big groups. Enjoy the outdoors in beautiful sunny Florida. With a stone through away from all the major attractions, highways, shop.......read more

4 Bedroom(s)
1 Bath(s) - Sleeps 10 House Rentals

Vacation Home

Vacation Rentals - Winter Park Condo

Chic Lakeside Midcentury Modern Retreat

Midcentury meets modern and chic and meets you right in the heart of downtown for your next stay in Winter Park. Whether you're brought to the area for business and need the best in proximity to the area's most important and sought after meeting and entertaining spots, or need a tranquil yet visually compelling lakeside spot to finish your novel this is the place. We've loved this condo for as long as we've had it and finally completed the redesi.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Condo Rentals

Vacation Home

Apt D - Winter Park Apartment

Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths

Location!!! Beautifully appointed 2 bedroom, 2 bath second floor apartment overlooking a beautiful pool area with balcony. Just three blocks to Park Ave and two blocks to the Winter Park Village! Many great restaurants and shops are within walking distance as well as parks and stadium seating movie theater. 10' ceilings, beautiful acacia wood flooring with high-end appliances and fixtures throughout. Huge flat screen tv with cable and Netflix .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Apartment Rentals

Vacation Home

Urban Oasis w/ Home Office - Winter Park Condo

Lakefront Condo w/ Sunroom, Office, & Lakeside Pool

Welcome to beautiful Winter Park, Florida and your home away from home in your lakeside, super-convenient 1 bedroom /1 home office condo. Designed with the working traveler in mind, or locals needing a temporary space, we offer you an attention to detail not commonly found in most short term rentals. At Urban Oasis, you will enjoy the many amenities of the private lakefront park, an enclosed sunlit patio, a dedicated office, and fast access to al.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 2 Condo Rentals

Vacation Home

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