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Winter Park Vacation Rentals

Large selection of Winter Park Vacation Rentals, book your property Direct and Save!

Many rental properties to choose from, including private Homes, Cottages or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities that will make your Florida visit the perfect getaway.

Charming Clean Home near Corrine Drive / East End Market 30 day minimum stay

Winter Park Vacation Rental Star 5.0 Star Review

Winter Park home ready for your event, vacation or executive rental.
Updated kitchen, granite countertops, wood floors, granite and slate.
Washer and dryer.
Bbq, 2 flat screen tvs, dvd, WiFi TV, Netflix, Prime Video & high speed internet.
1 queen bed, 2 full beds with feather beds and linens in each room. 1 sofa.
Open living area, more

3 Bedrooms - Sleeps 6
Vacation Rental Home in Winter Park

The Garden Room

Winter Park Vacation Rental

Welcome to The Garden Room in Winter Park! This unit is a 1/1 with a living room that flexes as a second bedroom, accommodating up to 4 guests. In addition to being close to Rollins College and the hotspots on Park Ave and Orange Ave, the unit is an easy walk to Winter Park\'s largest public park; 44 acre Mead Gardens (our namesake). We\'ll send more

1 Bedrooms - Sleeps 2
Vacation Rental Home in Winter Park

Cozy Comfort In The Heart of Winter Park!

Winter Park Apartment

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 more

2 Bedrooms - Sleeps 4
Apartment in Winter Park

Casa Winter Park

Winter Park Vacation Rental Star 4.9 Star Review

This property location is perfect to stay nearby Rollins College, Farmers Market, Casa Feliz, UCF and many more historic destinations in the Winter Park area.
Casa Winter Park modern design, accommodates the need for your personal space while enjoying, at the same time, the gathering with several family members under the same planned event. The more

4 Bedrooms - Sleeps 8
Vacation Rental Home in Winter Park

Luxury Villa, 3bed/2bath Great Location with Pool

Winter Park Vacation Rental Star 5.0 Star Review

Enjoy an elegant and modern villa in the heart of Winter Park, This home with 3 bedrooms, 2 bathrooms and a spectacular pool in the backyard to enjoy with the whole family are centrally loacated and close to all major theme park, Orlando Downtown and 10 minutes from romantic Park Ave and scenic boat tour of Winter Park. Walk to Pharmacy CVS, more

3 Bedrooms - Sleeps 9
Vacation Rental Home in Winter Park

Cute Guest House In Winter Park Minutes From Downtown in Car

Winter Park Apartment Star 4.6 Star Review

Enjoy our guest house and the new space we created in Oct 2015! The guest house has a kitchenette with two glass burners, refrigerator, coffee maker, toaster, convection microwave, AC wall unit, TV w/ HD antenna for over a dozen local channels (we\'ve cut the cord, but the TV is a smart TV with Netflicks, HBO Go, Amazon Prime Video), wifi (50Mbps), more

1 Bedrooms - Sleeps 2
Apartment in Winter Park

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

Winter Park Apartment

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 more

2 Bedrooms - Sleeps 4
Apartment in Winter Park

Luxury King Condo min from everything!

Winter Park Condo Star 4.7 Star Review

Welcome to luxury living. We\'re ready to transform your stay into a dream come true

You\'ll be staying in a modern, remodeled, fully furnished condo in the heart of Orlando. You\'ll be within walking distance to popular restaurants and shopping destinations! You will have free range of the condo including access to your own private more

1 Bedrooms - Sleeps 5
Condo in Winter Park

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