Vacation Rentals & Homes in Winter Park Florida

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........

10.0 Star Review

2 Bedrooms - Sleeps 4
Winter Park Vacation Rental
Pets Allowed

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, The Athlete Recovery Room, Warrior Yoga). Our neighborhood also has a gas station, 7-11 and ABC -all within 2 blocks walk. If you must get in a car,.......

1 Bedrooms - Sleeps 2
Winter Park Vacation Rental

In the heart of Winter Park, this charming 2-bedroom apartment offers non-stop chances for unwinding and exploring. Unwind by the sparkling outdoor pool while enjoying the convenience of free WiFi and a smart TV with satellite/cable channels. Indulge in home-cooked meals prepared in the fully stocked kitchen, complete with a stove, oven, refrigerator, grill, and all the necessary appliances and utensils. Enjoy your meals at the dining table, or step outside and fire up the grill for an alfresco .......

10.0 Star Review

2 Bedrooms - Sleeps 4
Winter Park Vacation Rental
Pets Allowed

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 community pool. Walmart, Publix, Costco, Target, and many restaurants are within a ten-minute drive. Orlando airport is about 20 to 25 minutes south on Semora.......

9.4 Star Review

4 Bedrooms - Sleeps 6
Winter Park Vacation Rental
Pets Allowed

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. Heated pool and hot tub! The pool, hot tub and grill stations are shared. Fastest internet speed available: 139MBPS download and 21.5 MBPS upload!.......

9.4 Star Review

2 Bedrooms - Sleeps 4
Winter Park Vacation Rental
Pets Allowed

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 offering fantastic sunset views and more! If you haven't explored Winter Park's Park Avenue, then you must!.......

10.0 Star Review

3 Bedrooms - Sleeps 6
Winter Park Vacation Rental
Pets Allowed

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 couches and chairs, new linens, two televisions (includes cable tv), central heat and air, new landscaping, irrigation and yard maintenance provided,.......

9.8 Star Review

2 Bedrooms - Sleeps 5
Winter Park Vacation Rental
Pets Allowed

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........

2 Bedrooms - Sleeps 8
Winter Park Vacation Rental
Pets Allowed

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 bungalow make this a wonderful vacation home that we hope your family will enjoy........

9.8 Star Review

2 Bedrooms - Sleeps 4
Winter Park Vacation Rental
Pets Allowed

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), utensils, plates / mugs. The guest house has a queen size CASPER bed (check it out online), great for couples or single travelers. Max we can take are.......

9.4 Star Review

1 Bedrooms - Sleeps 2
Winter Park Vacation Rental

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 connection. Wifi connected. Very comfortable fur.......

2 Bedrooms - Sleeps 4
Winter Park Vacation Rental
Pets Allowed

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 enjoyable........

9.8 Star Review

2 Bedrooms - Sleeps 4
Winter Park Vacation Rental

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 modern kitchen is fully stocked with basic cooking essential’s, a cozy living room with a smart tv, dining room with skylight.
Tastefully decorated .......

10.0 Star Review

3 Bedrooms - Sleeps 4
Winter Park Vacation Rental

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) and Disney's theme parks (34 miles). This house has 3 bedrooms and 2 bathrooms with a large fenced in back yard. The kitchen is fully furnished with a s.......

9.2 Star Review

3 Bedrooms - Sleeps 6
Winter Park Vacation Rental
Pets Allowed

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 speed available: 139MBPS download and 21.5 MBPS upload!.......

10.0 Star Review

2 Bedrooms - Sleeps 4
Winter Park Vacation Rental
Pets Allowed

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 Tour in operations since 1938.
All bookings require minimum 30 day stay!
Please message for pricing according to length of stay.


The .......

1 Bedrooms - Sleeps 2
Winter Park Vacation Rental

One month minimum to rent (30 nights).

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. Just minutes drive to grocery stores, bank and parks. It is truly convenient for everything! Come see it for yourself! Home away from home........

10.0 Star Review

3 Bedrooms - Sleeps 6
Winter Park Vacation Rental

Open kitchen / family room with dining area to comfortable seat 4, dining room and living room, screened in porch for watching sunsets, outdoor patio, 2 bedrooms each with a king size bed, large walk in shower in master bedroom, washer and dryer, 6 burner gas top stove and decor that celebrates Winter Park!
Cable TV in Family Room and Master Bed Room.
Games, Puzzles and Books
Outdoor Patio with table/chairs/ umbrella for anytime of day dining with an outdoor gas grill.
For rentals .......

10.0 Star Review

2 Bedrooms - Sleeps 4
Winter Park Vacation Rental

Welcome to Winter Park Citrus Escape! Our cozy 6-bed home (sleeps 8) is perfect for families and friends seeking a relaxing Florida vacation. As soon as you step inside, you'll feel at home in our tastefully decorated and fully equipped property.

Our living room features a comfortable sofa and recliner, a large 70” smart flat-screen TV, and a record player, perfect for creating a cozy and inviting atmosphere. Above the record player is our interactive vinyl wall art, where guests can ch.......

8.8 Star Review

3 Bedrooms - Sleeps 8
Winter Park Vacation Rental
Pets Allowed

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***.......

9.8 Star Review

2 Bedrooms - Sleeps 5
Winter Park Vacation Rental

Soak up the Florida sun and explore the Orlando area with ease from this 2-bed, 1-bath vacation rental in Winter Park! You’ll have everything you need for your extended stay, including a well-stocked kitchen, in-home laundry, and free WiFi. Plus, shopping and dining in Winter Park Village or on Park Avenue is just a short walk away! Ready to explore the area? Take the 6-mile drive to downtown Orlando for endless entertainment options. Disney World and Universal Studios are minutes away too!

10.0 Star Review

2 Bedrooms - Sleeps 4
Winter Park Vacation Rental
Pets Allowed

Location, Location, Location!!! Greatest location! Well appointed condo -one block from Park Avenue! This is a Downstairs unit. It is two bedroom / two bath - living room, separate dining room , split floor plan, enclosed porch and an additional private patio. There is a washer and dryer in the unit. 2 parking spaces. Walking distance to all the wonderful shops and restaurants. Located Next to Lake Virginia which has a jogging trail. Come stay with us and take a stroll down the famous brick-.......

2 Bedrooms - Sleeps 4
Winter Park Vacation Rental

Winter Park home ready for your event, vacation or executive rental.
Updated kitchen, granite countertops, wood floors, granite and slate.
Washer and dryer.
BBQ, 4 flat screen TVs, WIFI TV, Netflix, Prime Video & high speed internet.
1 King bed, 2 queen beds with feather beds and linens in each room. 1 sofa.
Open living area, screened in outdoor area viewing private fenced backyard.
2.5 miles to Park Ave, 1.3 miles to Baldwin Park
Convenient walking and running paths around.......

10.0 Star Review

3 Bedrooms - Sleeps 6
Winter Park Vacation Rental
Pets Allowed

Welcome to our charming 2-bedroom, 2-bathroom home nestled in the heart of Winter Park! Located just a short stroll away from Park Avenue, you'll find yourself immersed in the vibrant atmosphere of this highly desirable neighborhood. 



This home features natural wood flooring, bright natural light, and comfortable living areas, including a screened Florida Room. This home comes fully furnished with a king-size bed in the master bedroom and two twin-size beds in the second bedroom. F.......

2.0 Star Review

2 Bedrooms - Sleeps 6
Winter Park Vacation Rental

This cozy, quaint Winter Park home was built in 1925. The house has updated appliances and plenty of space. There are two big bedrooms with their own bathroom. Plus two single beds for guests. Do not forget our large dining and living room. We are mere minutes from historic Park Avenue where you have the finest in dining available. You can use the entire back yard and the private brick patio area for you and guests. Or take a stroll down to the lake where you may sit down and enjoy the sunset.

9.6 Star Review

2 Bedrooms - Sleeps 6
Winter Park Vacation Rental
Pets Allowed

Our home is located in Winter Park and can serve as a central base to live like a local. You can enjoy all of the great shops and restaurants on Park Avenue within driving distance from the home. The location is great to hit all the sites in Winter Park or drive to the theme parks, Outlets and experience Winter Park or Orlando as a local. The home is away from the tourist traps and in a secure neighborhood, just recommend renting a car to move around. Come stay here with the family or if you're .......

9.0 Star Review

3 Bedrooms - Sleeps 6
Winter Park Vacation Rental

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 e.......

8.0 Star Review

1 Bedrooms - Sleeps 4
Winter Park Vacation Rental
Pets Allowed

PET FRIENDLY 🐾 Book the Cloud 9 Suite, located in the heart of downtown Winter Park FL and Orlando! Beautifully furnished with updates, this Tiny Home will make you feel right at home. Close to Whole Foods/Publix, and Winter Park Village, which has a chain of retail, dining, and entertainment !.......

2 Bedrooms - Sleeps 2
Winter Park Vacation Rental

 Casa Winter Park accommodates the need for personal space while enjoying, at the same time, the gathering with several family members under the same planned event.  4 bedrooms , 4 baths , great pool , 2 gazebos. Dog friendly , no cats, pet fee required. 
2 min from Park Av Historic Winter Park , Rolling College ,  Full sail , Kraft Azalea Garden, 3 min from The  Morse Museum,  Casa Feliz Historic  Museum , Scenic Boat Tour, Winter Park Farmers Market, 

9.8 Star Review

4 Bedrooms - Sleeps 8
Winter Park Vacation Rental
Pets Allowed

Welcome to beautiful Winter Park, Florida and your home away from home in our trendy, super-convenient 1/1 King bed condo. Newly renovated, and furnished with upscale brands (West Elm, Restoration Hardware, Natuzzi) and attention to detail and comfort, you will enjoy sunlit spaces, a tropical retro vibe and easy access to all of the wonders of Winter Park, Orlando and the attractions........

10.0 Star Review

1 Bedrooms - Sleeps 2
Winter Park Vacation Rental

Warm and stylish getaway. Very spacious bedrooms open dining and family room. Relax outside with beautifully lit paved patio area. Great for the whole family! Pets are always welcome. Centrally located 5 minutes from downtown Winter Park 10 minutes from downtown Orlando 20 minutes away from theme parks........

3 Bedrooms - Sleeps 8
Winter Park Vacation Rental
Pets Allowed

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........

10.0 Star Review

2 Bedrooms - Sleeps 4
Winter Park Vacation Rental
Pets Allowed

Modern, clean and unique. Second floor penthouse unit overlooking the pool area. Gorgeous acacia wood floors, quartz counter tops, high-end cabinetry and fixtures, great new furnishings and mattresses, 8' solid core interior doors, high 10' ceilings, spacious open layout with a balcony offering fantastic sunset views 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 .......

10.0 Star Review

3 Bedrooms - Sleeps 6
Winter Park Vacation Rental
Pets Allowed

Our home has high quality furniture, linens, cookware and tableware for your family dinners. There are large and small appliances (including airfryer) to help with preparation.
Enjoy a fully-furnished 3 bedrooms, 2 baths, 1600 square-foot, single-story house in the heart of Winter Park, a wonderful town that is adjacent to Orlando and that is home to an array of restaurants, galleries, museums, up-scale shops, businesses, professional offices, parks, lakes and hiking and biking trails. Rol.......

10.0 Star Review

3 Bedrooms - Sleeps 5
Winter Park Vacation Rental

Beautiful Acacia wood flooring, with marble in the bathrooms and porcelain tile in the kitchen. Quartz countertops, ceilings are 10 feet high and there is a balcony with two sliding glass doors going to it from the master bedroom and living/family room. Very open floor plan. There is 1114 square feet of space inside, but it feels larger than that. Beautiful furnishings including an Italian leather couch. Large TV in the living room with the fastest WiFi available in the area - Hulu is programmed.......

8.0 Star Review

2 Bedrooms - Sleeps 4
WINTER PARK Vacation Rental
Pets Allowed

Enjoy our newly renovated home in Winter Park. We are centrally located and within minutes from Rollins College and Park Avenue. Downtown is only a short drive and the theme parks are a 30 minute drive. Our home comes fully stocked with everything you need to feel at home during your stay. The master bedroom comes equipped with a comfortable king size bed and a smart tv. Both t.v's in the house have firesticks so you can log into your streaming accounts. We allow pets(and charge a pet fee). Th.......

8.8 Star Review

2 Bedrooms - Sleeps 4
Winter Park Vacation Rental
Pets Allowed