What are the must-see attractions for a 2 days stay in Winter Park, FL?

For a two-day stay, you'd want to see the Charles Hosmer Morse Museum of American Art, which houses the largest collection of Tiffany glass anywhere. Then, head over to the scenic Rollins College campus, known for its beautiful architecture and lush gardens. You can also take a stroll along Park Avenue, Winter Park's main street, with its charming shops and restaurants.

What are the best apartments in Winter Park, FL?

Among the apartments in Winter Park, FL, Modern Tropical Pool Home , Downtown (Ivanhoe Village) Loft Apartment and Upscale Loft Space Close To Downtown are the most popular ones.

Which neighborhoods in Winter Park, FL are best for renting an apartment?

The best neighbourhoods for renting an apartment are generally considered to be the areas around Park Avenue, with its vibrant atmosphere and easy access to shops and restaurants, or the more residential areas of Winter Park Pines and the area surrounding the Winter Park Village, which offers a quieter and more family-friendly vibe.

What are the best apartments with a pool in Winter Park, FL?

Modern Tropical Pool Home , A Home Where Eclectic Luxury Meets Affordability and Condo\/apt - Near Disney - Universal - 3 Pools - Wifi - free Parking are the best apartments with a pool in Winter Park, FL.

What are the top cultural and historical sites in Winter Park, FL?

Winter Park is home to some great cultural and historical sites. The Albin Polasek Museum & Sculpture Gardens showcases the work of the renowned sculptor Albin Polasek, while the Morse Museum, as I mentioned, houses a stunning collection of Tiffany glass. For a glimpse into the city's history, visit the Winter Park Historical Museum, located in a charming old house.

What are the best apartments with a jacuzzi in Winter Park, FL?

The best apartments with a jacuzzi in Winter Park, FL are A Home Where Eclectic Luxury Meets Affordability , Condo\/apt - Near Disney - Universal - 3 Pools - Wifi - free Parking and Lakefront Studio Apartment (Private Entrance) .

What makes Winter Park, FL unique or famous?

Winter Park is famous for its beautiful natural setting, with its abundance of lakes and lush greenery. It's also known for its charming, walkable downtown area, lined with boutiques, art galleries, and restaurants. And of course, the city is home to Rollins College, a prestigious liberal arts institution that adds a touch of sophistication and intellectual energy to the area.

What are the best apartments for families and kids in Winter Park, FL?

The best apartments for families and kids in Winter Park, FL are Thornton Park's Historic Guest House - Private , Moniker Manor (Entire Home Near Downtown) and A Home Where Eclectic Luxury Meets Affordability .

Where can you find the best local markets and street food in Winter Park, FL?

The Winter Park Farmers' Market, held every Saturday morning at the Winter Park Village, is a great place to find local produce, artisanal goods, and a variety of food stalls. For street food, you can check out the food trucks that gather at various locations around town, particularly in the evenings.

What are the best pet friendly apartments in Winter Park, FL?

The best pet friendly apartments in Winter Park, FL are Modern Tropical Pool Home , Thornton Park's Historic Guest House - Private and A Home Where Eclectic Luxury Meets Affordability .

How is the public transportation system in Winter Park, FL?

Winter Park has a public transportation system, but it's not as extensive as in larger cities. The Lynx bus system offers service within the city and to nearby areas, but you'll likely need to rely on taxis or ride-sharing services for more extensive travel.

What are the best apartments with parking in Winter Park, FL?

Modern Tropical Pool Home , Downtown (Ivanhoe Village) Loft Apartment and Upscale Loft Space Close To Downtown are the best apartments with parking in Winter Park, FL.

Which seasonal events or festivals should apartment renters look forward to in Winter Park, FL?

Winter Park is known for its lively events. The Winter Park Sidewalk Art Festival, held in March, attracts artists and art lovers from across the country. In December, the city comes alive with holiday cheer during the Winter Park Christmas Parade and other festive events.

What amenities are typically included in apartments in Winter Park, FL?

Apartments in Winter Park often include standard amenities like central air conditioning, a washer and dryer, and a parking space. Some may also offer additional amenities, such as a swimming pool, fitness centre, or community room.

What leisure activities are available for relaxation in Winter Park, FL?

Winter Park offers a variety of leisure activities. You can relax by the lake at Mead Garden, enjoy a leisurely stroll through the scenic trails at the Kraft Azalea Garden, or take a boat ride on one of the many lakes. For a more active experience, you can rent a kayak or canoe and explore the waterways.

Winter Park, FL Holiday Apartments and Self Contained

9.0 80 reviews

Poolside Oasis Close To Theme Parks & Attractions

apartment, Altamonte Springs

This Altamonte Springs apartment is situated in a peaceful residential neighbourhood, just a short drive from the Altamonte Mall and Cranes Roost Park. It has received excellent ratings for its location, cleanliness and overall experience.
The property offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. The apartment comes equipped with a fully-equipped kitchen, air conditioning, a swimming pool, a garden, a bar, parking and internet access.

9.0 12 reviews

Under 15 Min To Downtown | Pooltable & Retro Games

apartment, Azalea Park

This three-bedroom, two-bathroom flat in Azalea Park offers excellent access to Downtown Orlando (under 24 kilometres), Orlando International Airport (32 kilometres), and the University of Central Florida (26 kilometres), placing you close to dining, shopping, and major attractions.
This modern apartment comfortably accommodates up to seven guests and features air conditioning, a kitchen, internet, and parking, making it an ideal base for work, school visits, or exploring the city.

10 2 reviews

Game Day Getaway-downtown Orlando

apartment, Orlando

This Orlando flat is located in the West Lake District, 1.1 kilometres from Camping World Stadium and 1.2 kilometres from Tinker Field.
This 4-bedroom, 2-bathroom flat sleeps 13 guests and offers a fully equipped kitchen with microwave and dishwasher, air conditioning, internet access, and on-site laundry facilities, with proximity to Orlando International Premium Outlets, Mall at Millenia, Universal Orlando Resort, and The Orlando Eye.

No reviews

1 Queen Bed

apartment, Fairview Shores

This apartment in Fairview Shores is located 9 kilometres from the Kia Centre and Church Street Station, and 11 kilometres from Camping World Stadium.
This 19 square metre studio flat accommodates two guests and features air conditioning, a private bathroom, a television, complimentary WiFi, a refrigerator, a microwave, and access to an outdoor swimming pool, with on-site private parking and a 24-hour front desk also provided.

9.8 16 reviews

Yania's Cozy Getaway

apartment, Azalea Park

This Azalea Park self-contained flat is conveniently located minutes from Waterford Lakes Town Centre and major highways, offering easy access to Orlando's theme parks.
The one-bedroom, one-bathroom apartment sleeps two guests and features a private patio, kitchenette with fridge and microwave, air conditioning, internet access, parking, and allows pets; nearby activities include fishing and exploring the area's attractions such as Florida Mall and Orlando International Premium Outlets.

9.5 39 reviews

A Cozy Retreat In The Heart Of The City!

apartment, Azalea Park

Golden Cove Rental, a three-bedroom house in Orlando's Azalea Park neighbourhood, is situated approximately 24km from Orlando International Airport, Interstate 4, and Orlando city centre.
This family-friendly property sleeps up to 10 guests, boasts a fully equipped kitchen with dishwasher, air conditioning, a garden, parking, and excellent guest reviews; nearby amenities include parks, shops, and restaurants.

9.2 5 reviews

Serenity Spring Lake King Suite

apartment, Conway

This Conway apartment, situated approximately 8 kilometres from Orlando International Airport and 6.4 kilometres from Church Street Station, offers easy access to Camping World Stadium and Holy Land Experience.
The 33-square-metre self-catering flat comprises one bedroom, one bathroom, and can accommodate three guests, featuring a fully equipped kitchenette, free Wi-Fi, private parking, and garden access.

9.4 183 reviews

Renovated Comfy Downtown Orlando Duplex. Sleeps 8.

apartment, Orlando

This Orlando duplex is centrally located, minutes from Lake Eola and Thornton Park, and a short 32-kilometre drive from the theme parks.
The stylish, fully-remodelled two-bedroom, two-bathroom property sleeps eight guests and features a fully equipped kitchen, free parking for two cars, and a unique Zen room with ensuite bathroom.

9.5 75 reviews

3bd In Downtown Orlando

apartment, Fairview Shores

This Fairview Shores holiday home enjoys a prime location opposite Dubsdread Golf Course, offering easy access to Universal Orlando Resort, Walt Disney World Resort, and SeaWorld Orlando.
Sleeping six guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen, air conditioning, a private garden with patio, and parking; modern furnishings and luxurious bedding complete this self-catering house.

10 63 reviews

Stylish & Cozy King Bed Retreat @ Baldwin Park

apartment, Orlando

This fully furnished two-bedroom house is situated near Baldwin Park, a short drive (minutes) from Downtown Orlando, Orlando International Airport (MCO), and several theme parks.
The 2-bathroom property, sleeping up to 5 guests, boasts a private backyard with a fire pit, high-speed internet, a fully equipped kitchen including a dishwasher, and keyless entry; peaceful walking trails are also nearby, with Downtown Disney easily accessible.

9.6 68 reviews

Private And Modern Couples Retreat Close To It All

apartment, Azalea Park

This Azalea Park apartment rental is conveniently located approximately 24km from Orlando International Airport (MCO) and central Orlando, and 48km from Walt Disney World Resort, Universal Orlando Resort, and SeaWorld.
The self-contained one-bedroom flat offers guests a private patio, kitchenette with fridge, freezer and microwave, free parking for two cars, smart TV with streaming services, free Wi-Fi, and access to a shared laundry.

8.6 4 reviews

King Bed Escape: Private Patio, Grill, Fire Pit Near Everything In Orlando

apartment, Azalea Park

This Azalea Park apartment, ideally situated in Orlando, offers easy access to Downtown Orlando, the University of Central Florida, and Orlando International Airport.
The 70-square-metre self-catering flat comprises one bedroom, one bathroom, sleeps four, and boasts a private backyard with a barbecue and fire pit, a fully equipped kitchen, and a smart TV.

Best family friendly Winter Park, FL Holiday Apartments and Self Contained Accommodations

Among the 321 accommodations in Winter Park, FL, here are the 4 best family friendly holiday apartments

9.8 39 reviews

Travel Themed Property With Backyard Oasis

apartment, Casselberry

This six-bedroom apartment is located in Maitland, a suburb of Orlando, just 15 kilometres from Casselberry and within walking distance of a Walmart Supercenter and various restaurants. The apartment is rated excellent by previous guests and offers a comfortable and convenient base for exploring the many attractions of Orlando.
The apartment spans 232 square metres and comfortably accommodates up to 14 guests. It features a private pool, an outdoor kitchen, a fire pit, a game room, a travel-themed design, and a separate one-bedroom "Castaway Island" apartment.

8.0 1 review

3 Bedroom Corner Suite

apartment, Orlando

This Orlando apartment is situated in the South Eola district, a short walk from Lake Eola and within 2km of Church Street Station.
The 186 square metre property offers three bedrooms, two bathrooms, sleeps six, and includes a balcony, free Wi-Fi, covered parking, and is close to Universal Orlando Resort and other attractions.

9.7 116 reviews

The Sunrise House

apartment, Orlando

This Orlando bungalow, situated in the Audubon Park district, offers easy access to Mills 50's attractions, Downtown Orlando (8km), and Winter Park (6km), placing guests within convenient reach of major theme parks.
Sleeping up to nine guests, the three-bedroom, one-bathroom property boasts a mid-century modern design, including smart TVs, a dedicated workspace, laundry facilities, and a garden; nearby activities include exploring Audubon Park and enjoying the local breweries and restaurants.

9.4 46 reviews

Florida Vacation With Pool Fun For Families

apartment, Casselberry

This charming three-bedroom house is located in Casselberry, just 5km from Altamonte Mall and within 10km of Cranes Roost Park and Red Bug Lake Park, offering easy access to shopping and outdoor activities. The property consistently receives excellent ratings for location, cleanliness, and overall user experience.
The house comfortably accommodates up to 7 guests and provides a fully equipped kitchen, a private pool, a garden with barbecue facilities, and free Wi-Fi. Enjoy the Florida sunshine with al fresco dining and relax by the pool, while exploring the nearby golf courses and parks.

Best Winter Park, FL holiday apartments with a kitchen

9.9 153 reviews

Spacious 3 Br Home Perfect For Orlando Getaway

apartment, Casselberry

This Casselberry house, near Dew Drop Park, offers easy access to Orlando's major attractions, including Disney World and Universal Studios, a short drive away (distances vary depending on the specific attraction).
The three-bedroom, two-bathroom property sleeps six, features a fully equipped kitchen with dishwasher, free parking, a fenced backyard, and Wi-Fi; nearby activities include the park's lake, playground, and pavilion.

8.6 11 reviews

7.3miles To Airport + 20miles To Disney + 8.2miles To Dt!

apartment, Orlando

This house is located in Orlando, just 800 metres from Ventura Country Club and within 10 kilometres of several shopping centres, offering a peaceful retreat close to amenities. It has received excellent user ratings, making it a popular choice for travellers.
The property features three bedrooms, two bathrooms, and can accommodate up to 10 guests. The house is equipped with a fully fitted kitchen, air conditioning, a terrace, a garden, and parking, providing everything you need for a comfortable stay.

10 4 reviews

Mills 50 1br | Sleeps 4 | Workspace | Free Parking

apartment, Orlando

This 1-bedroom flat is located in Orlando's Mills 50 arts district, a walkable area with murals and dining, and is a short drive to Downtown Orlando, AdventHealth, and entertainment venues like the Kia Centre, approximately 7.4 kilometres away.
This flat accommodates up to four guests with a queen bed and sofa bed, offering a spa-style bathroom with rainfall shower, a dedicated workspace with natural light, and is equipped with a fridge, freezer, microwave, air conditioning, and parking, with pets welcome.

8.4 11 reviews

New! Modern Home - 4 Beds 2.5 Baths - 5 Minutes From Downtown

apartment, Orlando

This Orlando apartment rental, located in the Holden-Paramore district, is a 15-minute walk from the Kia Center and 12 minutes from Grand Avenue Park, offering easy access to Universal Orlando Resort and ICON Park (short drive).
The four-bedroom, two-and-a-half-bathroom property sleeps ten guests and includes amenities such as Wi-Fi, a fully equipped kitchen, in-unit laundry, and covered parking.

Frequently asked questions about apartment rentals in Winter Park, FL

What are the must-see attractions for a 2 days stay in Winter Park, FL?
For a two-day stay, you'd want to see the Charles Hosmer Morse Museum of American Art, which houses the largest collection of Tiffany glass anywhere. Then, head over to the scenic Rollins College campus, known for its beautiful architecture and lush gardens. You can also take a stroll along Park Avenue, Winter Park's main street, with its charming shops and restaurants.
What are the best apartments in Winter Park, FL?
Among the apartments in Winter Park, FL, Modern Tropical Pool Home , Downtown (Ivanhoe Village) Loft Apartment and Upscale Loft Space Close To Downtown are the most popular ones.
Which neighborhoods in Winter Park, FL are best for renting an apartment?
The best neighbourhoods for renting an apartment are generally considered to be the areas around Park Avenue, with its vibrant atmosphere and easy access to shops and restaurants, or the more residential areas of Winter Park Pines and the area surrounding the Winter Park Village, which offers a quieter and more family-friendly vibe.
What are the best apartments with a pool in Winter Park, FL?
Modern Tropical Pool Home , A Home Where Eclectic Luxury Meets Affordability and Condo\/apt - Near Disney - Universal - 3 Pools - Wifi - free Parking are the best apartments with a pool in Winter Park, FL.
What are the top cultural and historical sites in Winter Park, FL?
Winter Park is home to some great cultural and historical sites. The Albin Polasek Museum & Sculpture Gardens showcases the work of the renowned sculptor Albin Polasek, while the Morse Museum, as I mentioned, houses a stunning collection of Tiffany glass. For a glimpse into the city's history, visit the Winter Park Historical Museum, located in a charming old house.
What are the best apartments with a jacuzzi in Winter Park, FL?
The best apartments with a jacuzzi in Winter Park, FL are A Home Where Eclectic Luxury Meets Affordability, Condo\/apt - Near Disney - Universal - 3 Pools - Wifi - free Parking and Lakefront Studio Apartment (Private Entrance).
What makes Winter Park, FL unique or famous?
Winter Park is famous for its beautiful natural setting, with its abundance of lakes and lush greenery. It's also known for its charming, walkable downtown area, lined with boutiques, art galleries, and restaurants. And of course, the city is home to Rollins College, a prestigious liberal arts institution that adds a touch of sophistication and intellectual energy to the area.
What are the best apartments for families and kids in Winter Park, FL?
The best apartments for families and kids in Winter Park, FL are Thornton Park's Historic Guest House - Private, Moniker Manor (Entire Home Near Downtown) and A Home Where Eclectic Luxury Meets Affordability.
Where can you find the best local markets and street food in Winter Park, FL?
The Winter Park Farmers' Market, held every Saturday morning at the Winter Park Village, is a great place to find local produce, artisanal goods, and a variety of food stalls. For street food, you can check out the food trucks that gather at various locations around town, particularly in the evenings.
What are the best pet friendly apartments in Winter Park, FL?
The best pet friendly apartments in Winter Park, FL are Modern Tropical Pool Home , Thornton Park's Historic Guest House - Private and A Home Where Eclectic Luxury Meets Affordability.
How is the public transportation system in Winter Park, FL?
Winter Park has a public transportation system, but it's not as extensive as in larger cities. The Lynx bus system offers service within the city and to nearby areas, but you'll likely need to rely on taxis or ride-sharing services for more extensive travel.
What are the best apartments with parking in Winter Park, FL?
Modern Tropical Pool Home , Downtown (Ivanhoe Village) Loft Apartment and Upscale Loft Space Close To Downtown are the best apartments with parking in Winter Park, FL.
Which seasonal events or festivals should apartment renters look forward to in Winter Park, FL?
Winter Park is known for its lively events. The Winter Park Sidewalk Art Festival, held in March, attracts artists and art lovers from across the country. In December, the city comes alive with holiday cheer during the Winter Park Christmas Parade and other festive events.
What amenities are typically included in apartments in Winter Park, FL?
Apartments in Winter Park often include standard amenities like central air conditioning, a washer and dryer, and a parking space. Some may also offer additional amenities, such as a swimming pool, fitness centre, or community room.
What leisure activities are available for relaxation in Winter Park, FL?
Winter Park offers a variety of leisure activities. You can relax by the lake at Mead Garden, enjoy a leisurely stroll through the scenic trails at the Kraft Azalea Garden, or take a boat ride on one of the many lakes. For a more active experience, you can rent a kayak or canoe and explore the waterways.

Popular destinations

Best Winter Park, FL holiday apartments with air conditioning

10 204 reviews

Stylish Newly Updated Home In Winter Park

apartment, Fairview Shores

This Fairview Shores apartment is conveniently located just 16km from Orlando's main attractions, offering easy access to I-4 and the vibrant local amenities of Fairview Shores. It has received excellent ratings for its location, cleanliness, and user experience.
This spacious property comfortably sleeps 10 guests and features a well-equipped kitchen, a relaxing garden, and modern amenities like a smart TV and dimmable smart mirrors. The apartment also provides thoughtful touches like fragrance-free cleaning products, a dedicated workspace, and a fire extinguisher.

9.6 65 reviews

Downtown Private Efficiency Lake Eola Central Business District

apartment, Orlando

This studio apartment is located in downtown Orlando, just a short walk from Lake Eola, the Dr. Philips Center, Amway Arena, and Publix. It has received excellent user ratings, making it a popular choice for travellers.
The apartment is compact, measuring just 14 square metres, and includes a kitchenette, a private entrance, and a comfortable bedroom. It also offers access to streaming services, air conditioning, and parking.

9.9 192 reviews

Cozy Lakefront Apartment

apartment, Altamonte Springs

This apartment is located in Altamonte Springs, just a short distance from the tranquil shores of a lake and a pool, offering a peaceful escape from the hustle and bustle. It has received excellent ratings for user experience, location and cleanliness.
The flat is a private, detached second-floor unit above a garage, ideal for one guest. Amenities include a fully equipped kitchen, outdoor seating areas with lake and pool views, a swimming pool, and a garden. There is also parking available and guests are provided with coffee, tea, sweeteners, and spring water.

10 21 reviews

Elvis Studio Near Ucf | Private | Ev | Parking

apartment, Goldenrod

Villa Elvis is a luxury studio in Orlando, Goldenrod, situated 16 kilometres from UCF, 24 kilometres from Camping World Stadium, 24 kilometres from Downtown Orlando, and 40 kilometres from Universal Studios.
This pet-friendly apartment offers a private entrance, terrace, dedicated workspace, fully equipped kitchen, in-unit laundry, and an on-site EV charger for up to two guests.

Best pet-friendly Winter Park, FL holiday apartments

Among the 321 accommodations in Winter Park, FL, here are the 4 best pet friendly holiday apartments

9.9 31 reviews

Neón Lake House Retreat In Downtown Orlando

apartment, Orlando

This retro-boho flat offers a waterfront escape on a peaceful lake, just a short drive from Downtown Orlando's attractions including Lake Eola Park, the Amway Centre, and the Dr. Phillips Centre for the Performing Arts.
This five-bedroom, three-bathroom flat accommodates up to 14 guests, featuring a fully equipped kitchen, air conditioning, a swimming pool, parking, and direct lake access for outdoor relaxation.

9.5 22 reviews

Cozy Pet Friendly Home Near Cp Wp And Downtown

apartment, Fairview Shores

This Fairview Shores house is conveniently located just 6km from Downtown Orlando, and within a short drive of Universal Studios Florida (23km) and Walt Disney World Resort (35km).
Sleeping 15 guests, this five-bedroom, four-bathroom property boasts a fully equipped kitchen with dishwasher, air conditioning, private parking, Wi-Fi, and a fenced rear yard; nearby Wekiva Springs State Park offers opportunities for outdoor recreation.

9.5 52 reviews

Citrus Oasis: 4br Pool Home

apartment, Goldenrod

This Goldenrod apartment, perfect for families or groups of up to eight, boasts four bedrooms, two bathrooms, and a private pool and hot tub, located in a secluded area of Goldenrod; the precise distance to local attractions is unspecified.
The self-catering property features a fully equipped kitchen, open-plan living space, and additional amenities including a garden, parking, and high-speed internet access.

No reviews

Close To Camping World, Kia Center, City Soccer

apartment, Orlando

This Orlando flat is located in a quiet residential area, 2.1 kilometres from Camping World Stadium and 6.4 kilometres from Downtown Orlando.
This 98 square metre residence offers three bedrooms, two bathrooms, and sleeping arrangements for up to eight guests, with amenities including air conditioning, a kitchen with a fridge and microwave, and a screened patio, while being pet-friendly with a fenced garden.

Best apartment offers in Winter Park, FL

321 Holiday apartments in Winter Park, FL

Poolside Oasis Close To Theme Parks & Attractions