Vacation Rentals & Homes in Winter Park Florida

Winter Park Apartment

This is a downstairs end apartment with a back door that opens directly onto the pool deck near the hot tub. The apartment has wood floors, high ceilings, great furniture, fixtures and finishes and the kitchen has everything you need to prepare meals etc.
Excellent location! Just two blocks to the Winter Park Village and 3 to Park Ave........read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Winter Park Private vacation home

Welcome to our Winter Park home behind East End Market ! You will fall in love with this area which is full of friendly and walkable restaurants, bars, boutique shops, yoga studio and a wellness center offering saunas, cryotherapy and massage - (search The Lovely, Domu, East End Market, Gideon's Bakehouse, The Salty, Sushi Lola's, Redlight Redlight.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2

Vacation Home

Winter Park Private vacation home

Centrally located. Quiet neighborhood. Swimming pool with diving board and lots of toys, floaties. Pool table recently upgraded. Lots of room to stretch out. Master bedroom has king size bed with bath. 1 queen size beds and a full size bunk bed.. Coffee bar, oh and Hot tub Come try my slice of paradise........read more

4 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Winter Park Apartment 5.0

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 e.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Winter Park Villa 5.0

This villa is centrally located in East Winter Park just off 436 between Aloma and Howell Branch Road with easy access to the Casselberry, Maitland, Altamonte Springs, and the Oviedo areas. Convenient to Winter Park Hospitals, urgent care facilities, Full Sail, and UCF. There is a two-car driveway, a covered patio in the back, and use of a communit.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 7

Vacation Home

winter park Private vacation home 4.6

Welcome to our Breezy Winter Park Home where you can relax and enjoy! The home is situated in a short drive to Downtown Winter Park, Downtown Orlando, about 8 minutes drive to Starbucks, Ross, Publix, 7-elever, Walmart and restaurant and bars, a short drive to UCF and Rollin College Winter Park! No matter you are here for vacation or for work, you .......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Winter Park Apartment

Azul Baldwin Park Apartments is a vibrant property where Landing offers fully furnished 1-bedroom, 2-bedroom, and 3-bedroom apartments stocked with everything you need to feel at home.

Azul Baldwin Park Apartments is in a community that includes a Grilling Stations, an Outdoor Space, and a Pool. Azul Baldwin Park Apartments is in a very walk.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2

Vacation Home

Winter Park Private vacation home 5.0

Lovely private home located just minutes from the quaint and historic Downtown Winter Park. There is a Large backyard with porch, fire pit, deck, new chairs/tables, and screened porch. Outside there is also a hammock, ping pong table, and propane grill (bbq). There is ample parking available in the driveway and street.

The house has three b.......read more

3 Bedroom(s)
1 Bath(s) Sleeps 6

Vacation Home

Winter Park Private vacation home

Welcome to our charming 2 bedroom house in the heart of Winter Park, Florida! This beautiful home is the perfect retreat for families, couples, or friends seeking a relaxing and comfortable stay in one of the most sought-after neighborhoods in the area - less than 10-mins to downtown Orlando. 5-mins to grocery & convenience stores, 8-mins to restau.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 5

Vacation Home

Winter Park Condo 5.0

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 th.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Winter Park Apartment 4.7

Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two blocks to the Winter Park Village! Cozy and modern space. Outdoor grill and bikes for your enjoyment. Enjoy the convenience and tranquility of one of Florida's greatest walking communities while residing in style and sophistication. He.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Winter Park Apartment 5.0

About this space
Cook in or don't in this private and luxurious yet serene studio, where fun mid century meets old florida and cabana style. All furnishings are interior designer specified. It has plenty of basic cooking supplies and ample closet and bathroom storage. Luxe quality bedding. The back wall is papered in handmade papers to provide a.......read more

1 Bedroom(s)
2 Bath(s) Sleeps 3

Vacation Home

Winter Park Private vacation home 5.0

Beautiful furnished and fully equipped kitchen 4-bedroom, 3-bath home which sits on a large fenced corner lot in a highly desirable area of Winter close to ADVENT HEALTH HOSPITAL, CASA FELIZ, LEU GARDENS, ROLLINS COLLEGE, PARK AVE SHOPPING & DINING AREAS!!!
The floor plan is perfect for family living. Charming outdoor areas and all living spa.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 12

Vacation Home

Winter Park Private vacation home

Enjoy a stylish experience at this centrally-located place. MillsHouse is conveniently located for a foodie adventure. The best of Winter Park and Mills 50 is just blocks away.


✅ minutes to Lake Eola, Park Ave, Mills 50, shopping, parks and highways

✅ Covid-19 enhanced cleaning

✅ Walk to many winter park restaurantsread more

3 Bedroom(s)
2 Bath(s) Sleeps 11

Vacation Home

Winter Park Private vacation home 5.0

Your family will be close to everything when you stay at this centrally-located place.
The house is very spacious and was recently renovated.
It has a pool and an outdoor kitchen plus a covered patio.
Is just outside of the historic district of Winter Park and within a short drive to downtown Orlando, theme parks, airport etc.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 5

Vacation Home

Winter Park Private vacation home

Welcome to Winter Park! We are located conveniently off of the interstate and close to everything. Join us in our charming home that's ideally located to almost everything you need! Lots of malls, downtown orlando, and park avenue are also in close proximity. This place is especially good for adventurers, business travelers, or students! From last .......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Winter Park Private vacation home

It's your own private one-room structure with a private entrance next to a parking space. It's much like a hotel room inside, with microwave and counter-high fridge. The twin-size daybed has a surprise twin beneath it to roll out when needed. Windows on three walls. Walk-in closet. Outside the door: a little pool of blue water and dolphins spouting.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2

Vacation Home

Winter Park Apartment

Modern, clean and unique. Fastest internet speed available: 139MBPS download and 21.5 MBPS upload! Second floor penthouse unit overlooking the pool area. Gorgeous acacia wood floors, quartz counter tops, high-end cabinetry and fixtures, new furnishings and mattresses, 8' solid core interior doors, high ceilings, spacious open layout with a balcony .......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6

Vacation Home

Winter Park Cottage 4.9

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, comfortable bedding, mid century.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 5

Vacation Home

Winter Park Private vacation home

Your backyard oasis awaits you, with queen size 10in memory foam swing mattress, full outdoor kitchen, 65in TV along with a 2 hole putting green and flower wall. You can relax and enjoy the warm florida winters with a nice bbq.

Walking distance to phelps park, 1 mile from park ave, 1.5 mile from Rollins college and plenty more........read more

2 Bedroom(s)
1 Bath(s) Sleeps 8

Vacation Home

Winter Park Private vacation home 5.0

Just what you have been waiting for; beautiful cottage home in the heart of Winter Park! 2 bedroom/2 bath only steps away from the art festival and all the wonderful shops and restaurants on Park Avenue. Newly renovated bright home with rich wood floors, updated kitchen and charm throughout. The convenience, comfort, and uniqueness of this bungalo.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Winter Park Private vacation home 4.8

2 bedroom 2 bath, 1350 sqft detached home
Family friendly layout with master bedroom suite, shared bedroom (2 twin beds), main living room furnished with a coastal feel. Master bedroom has a Westin Heavenly Mattress. Twin Mattresses are Twin XL, one is the Serta CF 3000 Plush Hybrid and the other is the Serta CF 3000 Medium Hybrid. Kitchen w.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Winter Park Apartment 4.6

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), .......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2

Vacation Home

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 flo.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Winter Park Private vacation home

Welcome home to your pondside retreat, perfect for relaxing longer stays with access to all the best of Central Florida. Ten minutes from Park Ave, museums, boat tours, fine dining and 1 hour to beach........read more

4 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Winter Park Private vacation home 4.9

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 corpora.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Winter Park Apartment 5.0

Indulge the senses in the calming aesthetics of this newly constructed guest house.
The residence features room for 4 guests across 2 bedrooms, a large bathroom with a walk-in shower that features dual shower heads & skylight.
A desk for remote workers, and plenty of room to spread out across the common (indoor & outdoor) areas.
Your mod.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Winter Park Private vacation home 4.8

Charming Farmhouse Themed cottage in beautiful Winter Park, FL. This home is centrally located near Rollins College (4 miles), UCF (6.5 miles), and Full Sail University (1.8 miles) as well as just a short drive away from Park Avenue in Winter Park (4.5 miles) and a hop, skip and a jump away from 417 which takes you to Downtown Orlando (11 miles) an.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Winter Park Apartment

Enjoy this PRIVATE and Sparkling clean entire home, first floor 2 bedroom/1 full bath luxury apartment near Park Avenue! Municipal golf course just a few blocks away. Tons of restaurants and bars nearby. Movie theatre just two blocks away, Publix supermarket two blocks away, Whole Foods 1/2 mile away and Trader Joe's 3/4 mile away. Fastest internet.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Winter Park Private vacation home

Welcome to Historic Winter Park Florida. Central Florida's gem Winter Park is filled with history, whimsy and magic as it is home to Rollins College, the Morse Museum with the world's most comprehensive collection of works by Louis Comfort Tiffany, delicious restaurants, Saturday Farmer's Market, unique stores along Park Avenue and the Scenic Boat .......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2

Vacation Home

Winter Park Apartment

You will fall in love with this beautiful fully furnished 2 bedroom 1 bathroom unit. It is conveniently located just steps from a peaceful walking/biking trail and golf course. The property has a wonderful pool, bocce ball court, grills and a fire pit. Come relax and enjoy!.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 3

Vacation Home

Winter Park Apartment 5.0

Tucked away in a peaceful cove, Studio Blue offers a relaxing retreat in the heart of Orlando. Enjoy serene morning walks through Mead Garden or 5 star dinners at one of the many locally owned restaurants lining Mills avenue. Here you're at the center of it all! Don't let the size fool you. Studio Blue packs all the amenities you need for work, pla.......read more

Studio
1 Bath(s) Sleeps 2

Vacation Home

Winter Park Villa 2.5

Unwind in our 4BR, 2BA tropical oasis in Winter Park, Florida. Sleeping 8, our home is a one-story delight featuring a private outdoor pool and custom Orlando skyline mural. With a designer bathroom, bright kitchen, large dining table, and spacious living room, your comfort is guaranteed. Each room is thoughtfully designed, offering multiple sleepi.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Winter Park Private vacation home 5.0

One month minimum to rent.

A hidden gem, this meticulous sun-filled 3 BR + Office/2.5 bath home offers ultra- privacy, tucked in a wonderful and established neighborhood. Easy stroll to charming downtown Park Avenue for shopping, restaurants, cafes, bistros, wine bars, museums, Farmers market, Rollins college, Lake Virginia and much more. J.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6

Vacation Home

Winter Park Private vacation home

This comfortable home has all the amenities and is right in the heart of Winter Park. Walking distance to award-winning restaurants and shopping boutiques including East End Market. Explore downtown Winter Park just an 5 minute car ride away. 30 minute drive to the theme parks and 1 hour from the beautiful Florida beaches. .......read more

2 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Winter Park Private vacation home

This centrally located bungalow will leave you and your family close to everything! Located right off I-4, you will be 5 min from Downtown Orlando, 5-7 min from Downtown Winter Park, 15 min from Universal Studios, and 25 min from Disney! Many local parks and a golf course within walking distance!

This house comes equipped with a large 70 inc.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home